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Bridging chiral de-tert-butylcalix[4]arenes: Optical resolution based on column chromatography and structural characterization

  • Wen-Shan Liu EMAIL logo , Hong-Ying Li , Hai-Xia Zhang , Xiu-Yuan Han , Xi-Chun Guo and Chuan-Hua Ding EMAIL logo
Published/Copyright: March 2, 2022
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Open Chemistry
From the journal Open Chemistry Volume 20 Issue 1

Abstract

As the third-generation supramolecular main structure, calixarenes, especially chiral calixarenes, have been applied to various fields. In this study, the bridging chiral de-tert-butylcalix[4]arene derivatives with an amide group attached to a chiral point was synthesized for the first time, which provided a new group for its structural derivation at the bridging chiral position. The racemic compound 2 was optically resolved by column chromatography on silica gel with the aid of the chiral auxiliary (1S)-(+)-10-camphorsulfonyl chloride, and finally a pair of optically pure bridging chiral de-tert-butylcalix[4]arene derivatives 4a and 4b were obtained. The results of experimental and calculated ECD showed that compounds 4a and 4b were a pair of enantiomers, and their absolute configurations were designated S and R, respectively. This study provides new idea for the derivatization of specific chiral groups based on bridging chiral calix[4]arenes and their chiral resolution.

Graphical abstract

Keywords: de-tert-butylcalix[4]arene; (1S)-(+)-10-camphorsulfonyl chloride; synthesis; chiral resolution; ECD

1 Introduction

With its unique three-dimensional cavity structure, calixarene has become the third-generation supramolecular host molecule after crown ether and cyclodextrin. Calixarenes derivatives are widely used in biomedicine [1], nanoscience [2], and chemical sensors [3]. In particular, the application of chiral calixarenes derivatives in chiral recognition [4,5] and molecular asymmetric catalysis [6,7,8] has broad application prospects.

Intrinsically chiral calixarenes contain two major family members: inherently chiral calixarenes [9,10] and bridging chiral calixarenes [11,12,13]. Inherently chiral calixarenes are derived from asymmetric substitution only on the phenyl rings and (or) oxygen atom. The bridging chiral calixarenes exhibit asymmetric substitution on the bridged methylene group. Figure 1 takes de-tert-butylcalix[4]arenes as an example to show its two intrinsically chiral structures. Although inherently chiral calixarenes have been studied for decades and applied to many fields, its chiral recognition ability and asymmetric catalytic efficiency are often not satisfactory. The exciting thing is that the unique bridging chiral calixarenes will provide a platform for the construction of specific chiral hosts and catalysts and will point out a new direction for future development. However, there are two main reasons that limit the further application of bridging chiral calixarenes, one is the problem of optical purification of bridging chiral calixarenes, and the other is the lack of further derivable groups on the chiral structure, such as amide, amino, or carboxyl groups. Here, we focus on the derivation of amide group. As an important derivative group, amide can be modified to the required groups through reduction reaction, Hoffman degradation reaction, and so on.

Figure 1 Intrinsically chiral calix[4]arenes: (a) shows inherently chiral calixarenes and (b) shows bridging chiral calixarenes.
Figure 1

Intrinsically chiral calix[4]arenes: (a) shows inherently chiral calixarenes and (b) shows bridging chiral calixarenes.

In this study, we introduced an amide group on the chiral group of the chiral calixarenes for the first time and used chiral auxiliary (1S)-(+)-10-camphorsulfonyl chloride to perform optical resolution on it by column chromatography. The absolute configurations of the enantiomers 4a and 4b were determined by electron circular dichroism (ECD) experiment and calculation. This study provides a new method for the structure derivation and chiral resolution of bridging chiral calix[4]arenes.

2 Results and discussion

Using de-tert-butylcalix[4]arenes as the starting material, bridging chiral de-tert-butylcalix[4]arene derivative 1 monobridge-substituted with an equatorial N,N′-dimethylformamidyl group could be prepared through a homologous anionic ortho-Fries rearrangement in high yield [9]. As shown in the synthetic route of Figure 2, first, the N,N′-dimethylformamide group was hydrolyzed in toluene under the action of strong acid methanesulfonic acid and formed an unstable lactone structure with the phenol hydroxyl group on the ortho-benzene of the chiral center. The reaction solution did not require posttreatment, and ammonia water was added at 0°C to obtain the bridging chiral de-tert-butylcalix[4]arene with an equatorial amide group 2. Subsequently, (1S)-(+)-10-camphorsulfonyl chloride was used as a chiral auxiliary, and under the action of Cs2CO3 in CH3CN at room temperature, a nucleophilic substitution reaction occurred with the phenolic hydroxyl group on compound 2 to obtain a pair of diastereomeric mixtures 3a and 3b. The molar ratio between the chiral auxiliary and compound 2 was 1:1. Fortunately, the R f values of the diastereomers 3a and 3b were 0.46 and 0.40, respectively, with visible separation points. They could be successfully separated through silica gel column chromatography, with the total yield reaching 86% (2a, 45%; 2b, 41%). Finally, the chiral auxiliary (1S)-(+)-10-camphorsulfonyl group on the diastereomers 3a and 3b was removed to obtain a pair of enantiomers 4a ( [ α ] D 25 = –7.7) and 4b ( [ α ] D 25 = +7.8) under alkaline conditions.

Figure 2 Reagents and conditions: (a) methanesulfonic acid, toluene, 120°C; (b) NH3·H2O, 0°C; (c) (1S)-(+)-10-camphorsulfonyl chloride, Cs2CO3, CH3CN, rt; and (d) NaOH, CH3CN/H2O, 80°C.
Figure 2

Reagents and conditions: (a) methanesulfonic acid, toluene, 120°C; (b) NH3·H2O, 0°C; (c) (1S)-(+)-10-camphorsulfonyl chloride, Cs2CO3, CH3CN, rt; and (d) NaOH, CH3CN/H2O, 80°C.

The theoretical ECD spectra of 4a and 4b were calculated by quantum chemistry method, according to the relative spatial relationship between the bridging center and propyl group, and compared with those of methanol. As shown in Figure 3a, at room temperature, the experimental ECD spectra of 4a and 4b in MeOH at a concentration of 1.0 × 10−4 g/L showed a pair of excellent mirror images, proving that they were a pair of enantiomers. As shown in Figure 3b, the ECD spectra of compounds 4a and 4b calculated at TD-B3LYP/6-31G (d)//B3LYP/6-31G (d) level showed an acceptable fit with their experimental spectra in terms of band form and sign with respect to wavelength. According to the results of ECD experiment and calculation, the absolute configurations of compounds 4a and 4b could be assigned as S and R, respectively.

Figure 3 (a) Experimental ECD spectra of 4a (black line) and 4b (red line) in MeOH and (b) calculated ECD spectra of 4a (blue line) at the TD-B3LYP/6-31G(d)//B3LYP/6-31G(d) level.
Figure 3

(a) Experimental ECD spectra of 4a (black line) and 4b (red line) in MeOH and (b) calculated ECD spectra of 4a (blue line) at the TD-B3LYP/6-31G(d)//B3LYP/6-31G(d) level.

In the process of hydrolyzing N,N-dimethylformamide in compound 1, we tried many hydrolysis reagents, including strong acids such as p-toluenesulfonic acid, concentrated hydrochloric acid, concentrated sulfuric acid, and trifluoroacetic acid, as well as some strong bases. However, these hydrolysis reagents were difficult to react. In the end, under our continuous attempts and efforts to replace the reaction solvent, we found that methane sulfonic acid had a good hydrolysis effect on the N,N-dimethylformamide group of compound 1. Compared with several strong acids tried before, methanesulfonic acid is more acidic, resulting in the hydrolysis of N,N-dimethylformamide. Interestingly, when analyzing the structure of compound 2, we were pleasantly surprised to find that during the hydrolysis of compound 1, a propoxy group in the structure was also hydrolyzed to a phenolic hydroxyl group, which had been confirmed by 1H NMR spectrum and high-resolution mass spectrometry. As shown in Figure 4, according to the intermolecular hydrogen bond (H-bond) interaction, the phenolic hydroxyl group after the hydrolysis of the propoxy group and the phenolic hydroxyl group on the two ortho-benzene rings, respectively, formed intramolecular H-bond interactions, which marked the chemical shift of the phenol hydroxyl group after the hydrolysis of propoxy group larger, and the peak shaped wider and shorter. This indicated that the activity of phenolic hydroxyl group after hydrolysis of propoxy group was significantly higher than that of phenolic hydroxyl group on two ortho-benzene rings, which was conducive to the hydrolysis of N,N-dimethylformamide and the formation of lactone. In addition, according to the hydrogen spectrum structure of compound 3a, it was found that after the resolution reagent reacted with the phenolic hydroxyl group, the broad and low peak disappeared, which further indicated that the resolution reagent reacted with the phenolic hydroxyl group after the hydrolysis of propoxy group.

Figure 4 The chemical shift and peak characteristics of hydroxyl functional groups in compounds 2 and 3a: (a) shows the structure of compound 2, (b) shows the hydroxyl peak in compound 2, (c) shows the structure of compound 3a, and (d) shows the hydroxyl peak in compound 3a.
Figure 4

The chemical shift and peak characteristics of hydroxyl functional groups in compounds 2 and 3a: (a) shows the structure of compound 2, (b) shows the hydroxyl peak in compound 2, (c) shows the structure of compound 3a, and (d) shows the hydroxyl peak in compound 3a.

3 Conclusion

As the main structure of the third-generation supramolecular, calixarenes have been widely used in various fields. This study focused on the structure of bridging chiral de-tert-butylcalix[4]arene and obtained the first bridging chiral de-tert-butylcalix[4]arene with an amide group attached to the chiral point. Using the chiral auxiliary (1S)-(+)-10-camphorsulfonyl chloride, the racemic compound 2 was optically resolved to obtain a pair of optically pure bridging chiral calix[4]arene derivatives 4a and 4b, and the experimental and calculated results of ECD spectra proved that they were a pair of enantiomers. This study provides a new method for the derivatization and resolution of bridging chiral calixarenes.

4 Experimental section

General information: All chemicals were purchased from commercial sources and used without further purification. 1H nuclear magnetic resonance (NMR) and 13C NMR spectra were recorded at 300 MHz (1H) and at 75.5 MHz (13C). CDCl3 (δ 7.26 ppm) or TMS (δ 0.00 ppm) was used as an internal standard for 1H NMR spectra, and CDCl3 (δ 77.00 ppm) or TMS (δ 0.00 ppm) was used as an internal standard for 13C NMR spectra. The following abbreviations are used to indicate the multiplicity in NMR spectra: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, and J indicates the NMR coupling constant measured in Hertz. The courses of the reactions were monitored by thin layer chromatography (TLC) using TLC aluminium sheets with Silica gel 60 GF254. The column chromatography was performed using Silica gel 60. Optical rotations were measured using a polarimeter with a 1 dm path length. Experimental circular dichroism spectra were recorded in a quartz cuvette of 1 mm optical path length. High-resolution mass spectra (HRMS) were measured on a mass spectrometer equipped with a time of flight (TOF) system and an electrospray ionization (ESI) ion source.

Compound 2. A mixture of compound 1 (3.00 g, 5.06 mmol) and methanesulfonic acid (1.64 mL, 25.30 mmol) in toluene (100 mL) was stirred at 110°C for 3 h. After the reaction was completed by TLC analysis, the heating device was removed, and the reaction temperature was reduced to 0°C under the condition of ice bath. A 25% aqueous ammonia solution (40 mL) was slowly added dropwise, and the reaction was stopped after stirring for 1 h. The mixture was extracted with CH2Cl2 (3 mL × 60 mL) and washed with saturated NaCl solution (3 mL × 60 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (PE:EA = 3:1) to obtain the intermediate 2 (1.65 g, 62% yield).

Compound 2: White solid. M.p. 196.5–198.2°C. 1H NMR (400 MHz, DMSO-d 6) δ 9.14 (s, 1H), 8.72 (s, 1H), 8.63 (s, 1H), 7.49 (t, 2H), 7.31 (d, J = 7.2 Hz, 1H), 7.07–7.21 (m, 6H), 6.92 (dd, J = 1.6 Hz, J = 7.2 Hz, 1H), 6.83 (t, 1H), 6.61–6.68 (m, 2H), 6.55–6.60 (t, 1H), 5.57 (s, 1H), 4.14–4.24 (m, 2H), 4.10 (d, J = 13.6 Hz, 1H), 4.01–4.07 (m, 1H), 3.88–3.97 (m, 1H), 3.58 (d, J = 13.2 Hz), 3.47 (s, J = 12.8 Hz, 1H), 3.42 (d, J = 13.6 Hz, 1H), 1.92–2.02 (m, 2H), 1.21 (t, 3H); 13C NMR (100 MHz, DMSO-d 6) δ 172.7, 150.8, 150.5, 150.4, 148.1, 132.8, 128.1, 128.0, 127.6, 127.6, 127.4 (3C), 127.3, 127.3, 127.1, 126.9, 126.5, 126.5, 125.5, 124.4, 119.8, 118.8, 118.3, 116.9, 77.0, 30.6, 29.8 (2C), 29.2, 21.7, 9.6 ppm. HRMS (ESI): calcd for C32H31NO5 [M + H]+ 510.2280; found 510.2278.

Compounds 3a and 3b. To a stirred solution of compound 2 (1.50 g, 2.86 mmol) in dry CH3CN (80 mL) was slowly added Cs2CO3 (2.80 g, 8.58 mmol) under ice-bath. After stirring for 10 min, (1S)-10-camphorsulfonyl chloride (1.08 g, 4.29 mmol) was added, the reaction was continued for 2.5 h at room temperature until the reaction was completed and quenched with dilute hydrochloric acid solution. The aqueous layer was extracted with CH2Cl2, extracted twice, and the combined organic layers were washed with saturated NaCl solution and dried over anhydrous Na2SO4. The resulting residue was purified by column chromatography on silica gel (PE: EA = 2:1) to obtain the intermediates 3a and 3b (0.93 g, 45% yield for 3a; 0.85 g, 41% yield for 3b).

Compound 3a: White solid. M.p. 225.5–227.3°C. 1H NMR (400 MHz, DMSO-d 6) δ 9.82 (s, 1H), 9.12 (s, 1H), 7.43 (d, J = 7.8 Hz, 2H), 7.25 (d, J = 7.8 Hz, 2H), 7.05–7.19 (m, 6H), 6.97 (t, 1H), 6.85 (t, 1H), 6.62–6.72 (m, 2H), 5.74 (s, 1H), 4.53 (d, J = 13.2 Hz, 1H), 4.17–4.25 (m, 1H), 3.95–4.10 (m, 4H), 3.55–3.66 (m, 2H), 3.51 (d, J = 14.4 Hz, 1H), 3.50 (d, J = 14.4 Hz, 1H), 2.31–2.47 (m, 2H), 2.17–2.28 (m, 2H), 2.19 (t, 1H), 1.98–2.06 (m, 2H), 1.57–1.67 (m, 1H), 1.44–1.52 (m, 1H), 1.13 (t, 3H), 1.02 (s, 3H), 0.92 (s, 3H); 13C NMR (101 MHz, DMSO-d 6) δ 212.2, 171.1, 151.3, 150.4, 147.8, 141.8, 134.2, 133.4, 132.5, 130.4, 129.3, 129.2, 128.7, 128.2, 128.1, 127.7, 127.7, 127.5, 127.3, 127.2, 126.0, 124.9, 124.5, 124.0, 120.4, 118.6, 77.3, 56.5, 46.8, 46.2, 41.2, 40.9, 29.9, 29.8, 29.2, 28.9, 25.1, 24.0, 21.4, 18.2, 18.0, 8.8 ppm. HRMS (ESI): calcd for C32H31NO5 [M + H]+ 724.2944; found 724.2942.

Compound 3b: White solid. M.p. 232.4–234.2°C. 1H NMR (400 MHz, DMSO-d 6) δ 9.83 (s, 1H), 9.11 (s, 1H), 7.49–7.42 (m, 2H), 7.27 (m, 2H), 7.21–7.04 (m, 6H), 6.98 (t, 1H), 6.92–6.81 (m, 1H), 6.67 (m, 2H), 5.75 (s, 1H), 4.53 (d, J = 13.1 Hz, 1H), 4.26–4.15 (m, 2H), 4.05 (d, J = 2.0 Hz, 1H), 4.01 (d, J = 2.1 Hz, 1H), 3.82 (d, J = 14.3 Hz, 1H), 3.68–3.57 (m, 3H), 3.51 (d, J = 13.6 Hz, 1H), 2.44–2.34 (m, 2H), 2.28–2.19 (m, 2H), 2.13 (t, J = 4.5 Hz, 1H), 2.04–1.96 (m, 2H), 1.68–1.62 (m, 1H), 1.50–1.44 (m, 1H), 1.18–1.08 (m, 6H), 0.92 (s, 3H); 13C NMR (101 MHz, DMSO-d 6) δ 213.1, 172.0, 152.3, 151.4, 148.9, 143.1, 135.3, 134.5, 133.5, 131.5, 130.2, 130.2, 129.9, 129.3, 129.2, 128.8, 128.8, 128.6, 128.4, 128.2, 127.1, 126.1, 125.6, 125.0, 121.5, 119.7, 78.4, 57.5, 48.0, 46.8, 42.5, 41.9, 31.0, 30.8, 30.4, 30.0, 26.2, 25.4, 22.5, 19.2, 19.1, 9.9 ppm. HRMS (ESI): calcd for C32H31NO5 [M + H]+ 724.2944; found 724.2939.

Compounds 4a and 4b. To a solution of compound 3a (or 3b) (0.5 g, 0.69 mmol) in CH3CN (30 mL) and water (10 mL) was added NaOH (0.14 g, 3.45 mmol). The reaction mixture was heated to 80°C and stirred for 1 h. The reaction mixture was evaporated to dryness under reduced pressure. The residue was neutralized with dilute hydrochloric acid and extracted with CH2Cl2 (30 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, and evaporated to dryness. The product was further purified by silica gel column chromatography (PE:EA = 3:1) to give 4a (or 4b) as a white powder (0.34 g, 94% yield for 4a; 0.33 g, 92% yield for 4b).

Compound 4a: White solid. M.p. 192.4–196.3°C. 1H NMR (400 MHz, DMSO-d 6) δ 9.14 (s, 1H), 8.72 (s, 1H), 8.65 (s, 1H), 7.44–7.56 (m, 2H), 7.30 (d, J = 6.8 Hz, 1H), 7.05–7.21 (m, 6H), 6.92 (d, J = 7.2 Hz, 1H), 6.83 (t, 1H), 6.61–6.68 (m, 2H), 6.58 (t, 1H), 5.57 (s, 1H), 4.14–4.25 (m, 2H), 4.10 (d, J = 13.6 Hz, 1H), 3.99–4.06 (m, 1H), 3.89–3.97 (m, 1H), 3.58 (d, J = 13.2 Hz, 1H), 3.39–3.51 (m, 2H), 1.90–2.05 (m, 2H), 1.21 (t, 3H); 13C NMR (101 MHz, DMSO-d 6) δ 173.7, 151.9, 151.6, 151.5, 149.2, 133.9, 129.2, 129.1, 128.7, 128.7, 128.6, 128.5 (3C), 128.4, 128.3, 128.2, 127.9, 127.6, 127.6, 126.5, 125.5, 120.8, 119.9, 119.3, 78.1, 31.6, 30.9, 30.2, 30.0, 22.8, 10.7 ppm. HRMS (ESI): calcd for C32H31NO5 [M + H]+ 510.2280; found 510.2277.

Compound 4b: White solid. M.p. 197.7.4–199.3°C. 1H NMR (400 MHz, DMSO-d 6) δ 9.10 (s, 1H), 8.67 (d, 2H), 7.45–7.57 (m, 2H), 7.31 (d, J = 6.8 Hz, 1 H), 7.05–7.20 (m, 6H), 6.92 (d, J = 7.2 Hz, 1H), 6.83 (t, 1H), 6.61–6.68 (m, 2H), 6.58 (t, 1H), 5.58 (s, 1H), 4.15–4.26 (m, 2H), 4.10 (d, J = 13.2 Hz, 1H), 3.99–4.07 (m, 1H), 3.88–3.98 (m, 1H), 3.58 (d, J = 13.6 Hz, 1H), 3.39–3.52 (m, 2H), 1.90–2.05 (m, 2H), 1.21 (t, 3H); 13C NMR (101 MHz, DMSO-d 6) δ 173.8, 151.9, 151.6, 151.5, 149.3, 133.9, 129.2, 129.1, 128.7, 128.7 (2C), 128.5 (3C), 128.4, 128.4, 128.2, 128.0, 127.6, 127.6, 126.6, 125.5, 120.8, 119.9, 119.4, 78.1, 31.6, 30.9, 30.2, 30.0, 22.8, 10.7 ppm. HRMS (ESI): calcd for C32H31NO5 [M + H]+ 510.2280; found 510.2278.

Acknowledgments

We thank Shandong Key Laboratory of Clinical Applied Pharmacology for its support.

  1. Funding information: This study is supported by the Medical and Health Science and Technology Development Project of Shandong Province of China (202013050426, 2019WS598).

  2. Author contributions: Wen-Shan Liu: conceptualization, writing – original draft, methodology; Hong-Ying Li: methodology, writing – original draft; Hai-Xia Zhang: formal analysis; Xiu-Yuan Han: data curation, validation; Xi-Chun Guo: software; and Chuan-Hua Ding: project administration, funding acquisition.

  3. Conflict of interest: The authors report no conflicts of interest in this study.

  4. Ethical approval: The conducted research is not related to either human or animal use.

  5. Data availability statement: The data used to support the findings of this study are included within the supplementary information file.

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Received: 2021-09-13
Revised: 2022-01-12
Accepted: 2022-01-26
Published Online: 2022-03-02

© 2022 Wen-Shan Liu et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  31. Cytotoxic activity of guaiane-type sesquiterpene lactone (deoxycynaropicrin) isolated from the leaves of Centaurothamnus maximus
  32. Effects of welding parameters on the angular distortion of welded steel plates
  33. Simulation of a reactor considering the Stamicarbon, Snamprogetti, and Toyo patents for obtaining urea
  34. Effect of different ramie (Boehmeria nivea L. Gaud) cultivars on the adsorption of heavy metal ions cadmium and lead in the remediation of contaminated farmland soils
  35. Impact of a live bacterial-based direct-fed microbial (DFM) postpartum and weaning system on performance, mortality, and health of Najdi lambs
  36. Anti-tumor effect of liposomes containing extracted Murrayafoline A against liver cancer cells in 2D and 3D cultured models
  37. Physicochemical properties and some mineral concentration of milk samples from different animals and altitudes
  38. Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies
  39. Diagnostic and therapeutic radioisotopes in nuclear medicine: Determination of gamma-ray transmission factors and safety competencies of high-dense and transparent glassy shields
  40. Calculation of NaI(Tl) detector efficiency using 226Ra, 232Th, and 40K radioisotopes: Three-phase Monte Carlo simulation study
  41. Isolation and identification of unstable components from Caesalpinia sappan by high-speed counter-current chromatography combined with preparative high-performance liquid chromatography
  42. Quantification of biomarkers and evaluation of antioxidant, anti-inflammatory, and cytotoxicity properties of Dodonaea viscosa grown in Saudi Arabia using HPTLC technique
  43. Characterization of the elastic modulus of ceramic–metal composites with physical and mechanical properties by ultrasonic technique
  44. GC-MS analysis of Vespa velutina auraria Smith and its anti-inflammatory and antioxidant activities in vitro
  45. Texturing of nanocoatings for surface acoustic wave-based sensors for volatile organic compounds
  46. Insights into the molecular basis of some chalcone analogues as potential inhibitors of Leishmania donovani: An integrated in silico and in vitro study
  47. (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity
  48. On the relative extraction rates of colour compounds and caffeine during brewing, an investigation of tea over time and temperature
  49. Characterization of egg shell powder-doped ceramic–metal composites
  50. Rapeseed oil-based hippurate amide nanocomposite coating material for anticorrosive and antibacterial applications
  51. Chemically modified Teucrium polium (Lamiaceae) plant act as an effective adsorbent tool for potassium permanganate (KMnO4) in wastewater remediation
  52. Efficiency analysis of photovoltaic systems installed in different geographical locations
  53. Risk prioritization model driven by success factor in the light of multicriteria decision making
  54. Theoretical investigations on the excited-state intramolecular proton transfer in the solvated 2-hydroxy-1-naphthaldehyde carbohydrazone
  55. Mechanical and gamma-ray shielding examinations of Bi2O3–PbO–CdO–B2O3 glass system
  56. Machine learning-based forecasting of potability of drinking water through adaptive boosting model
  57. The potential effect of the Rumex vesicarius water seeds extract treatment on mice before and during pregnancy on the serum enzymes and the histology of kidney and liver
  58. Impact of benzimidazole functional groups on the n-doping properties of benzimidazole derivatives
  59. Extraction of red pigment from Chinese jujube peel and the antioxidant activity of the pigment extracts
  60. Flexural strength and thermal properties of carbon black nanoparticle reinforced epoxy composites obtained from waste tires
  61. A focusing study on radioprotective and antioxidant effects of Annona muricata leaf extract in the circulation and liver tissue: Clinical and experimental studies
  62. Clinical comprehensive and experimental assessment of the radioprotective effect of Annona muricata leaf extract to prevent cellular damage in the ileum tissue
  63. Effect of WC content on ultrasonic properties, thermal and electrical conductivity of WC–Co–Ni–Cr composites
  64. Influence of various class cleaning agents for prosthesis on Co–Cr alloy surface
  65. The synthesis of nanocellulose-based nanocomposites for the effective removal of hexavalent chromium ions from aqueous solution
  66. Study on the influence of physical interlayers on the remaining oil production under different development modes
  67. Optimized linear regression control of DC motor under various disturbances
  68. Influence of different sample preparation strategies on hypothesis-driven shotgun proteomic analysis of human saliva
  69. Determination of flow distance of the fluid metal due to fluidity in ductile iron casting by artificial neural networks approach
  70. Investigation of mechanical activation effect on high-volume natural pozzolanic cements
  71. In vitro: Anti-coccidia activity of Calotropis procera leaf extract on Eimeria papillata oocysts sporulation and sporozoite
  72. Determination of oil composition of cowpea (Vigna unguiculata L.) seeds under influence of organic fertilizer forms
  73. Activated partial thromboplastin time maybe associated with the prognosis of papillary thyroid carcinoma
  74. Treatment of rat brain ischemia model by NSCs-polymer scaffold transplantation
  75. Lead and cadmium removal with native yeast from coastal wetlands
  76. Characterization of electroless Ni-coated Fe–Co composite using powder metallurgy
  77. Ferrate synthesis using NaOCl and its application for dye removal
  78. Antioxidant, antidiabetic, and anticholinesterase potential of Chenopodium murale L. extracts using in vitro and in vivo approaches
  79. Study on essential oil, antioxidant activity, anti-human prostate cancer effects, and induction of apoptosis by Equisetum arvense
  80. Experimental study on turning machine with permanent magnetic cutting tool
  81. Numerical simulation and mathematical modeling of the casting process for pearlitic spheroidal graphite cast iron
  82. Design, synthesis, and cytotoxicity evaluation of novel thiophene, pyrimidine, pyridazine, and pyridine: Griseofulvin heterocyclic extension derivatives
  83. Isolation and identification of promising antibiotic-producing bacteria
  84. Ultrasonic-induced reversible blood–brain barrier opening: Safety evaluation into the cellular level
  85. Evaluation of phytochemical and antioxidant potential of various extracts from traditionally used medicinal plants of Pakistan
  86. Effect of calcium lactate in standard diet on selected markers of oxidative stress and inflammation in ovariectomized rats
  87. Identification of crucial salivary proteins/genes and pathways involved in pathogenesis of temporomandibular disorders
  88. Zirconium-modified attapulgite was used for removing of Cr(vi) in aqueous solution
  89. The stress distribution of different types of restorative materials in primary molar
  90. Reducing surface heat loss in steam boilers
  91. Deformation behavior and formability of friction stir processed DP600 steel
  92. Synthesis and characterization of bismuth oxide/commercial activated carbon composite for battery anode
  93. Phytochemical analysis of Ziziphus jujube leaf at different foliar ages based on widely targeted metabolomics
  94. Effects of in ovo injection of black cumin (Nigella sativa) extract on hatching performance of broiler eggs
  95. Separation and evaluation of potential antioxidant, analgesic, and anti-inflammatory activities of limonene-rich essential oils from Citrus sinensis (L.)
  96. Bioactivity of a polyhydroxy gorgostane steroid from Xenia umbellata
  97. BiCAM-based automated scoring system for digital logic circuit diagrams
  98. Analysis of standard systems with solar monitoring systems
  99. Structural and spectroscopic properties of voriconazole and fluconazole – Experimental and theoretical studies
  100. New plant resistance inducers based on polyamines
  101. Experimental investigation of single-lap bolted and bolted/bonded (hybrid) joints of polymeric plates
  102. Investigation of inlet air pressure and evaporative cooling of four different cogeneration cycles
  103. Review Articles
  104. Comprehensive review on synthesis, physicochemical properties, and application of activated carbon from the Arecaceae plants for enhanced wastewater treatment
  105. Research progress on speciation analysis of arsenic in traditional Chinese medicine
  106. Recent modified air-assisted liquid–liquid microextraction applications for medicines and organic compounds in various samples: A review
  107. An insight on Vietnamese bio-waste materials as activated carbon precursors for multiple applications in environmental protection
  108. Antimicrobial activities of the extracts and secondary metabolites from Clausena genus – A review
  109. Bioremediation of organic/heavy metal contaminants by mixed cultures of microorganisms: A review
  110. Sonodynamic therapy for breast cancer: A literature review
  111. Recent progress of amino acid transporters as a novel antitumor target
  112. Aconitum coreanum Rapaics: Botany, traditional uses, phytochemistry, pharmacology, and toxicology
  113. Corrigendum
  114. Corrigendum to “Petrology and geochemistry of multiphase post-granitic dikes: A case study from the Gabal Serbal area, Southwestern Sinai, Egypt”
  115. Corrigendum to “Design of a Robust sliding mode controller for bioreactor cultures in overflow metabolism via an interdisciplinary approach”
  116. Corrigendum to “Statistical analysis on the radiological assessment and geochemical studies of granite rocks in the north of Um Taghir area, Eastern Desert, Egypt”
  117. Corrigendum to “Aroma components of tobacco powder from different producing areas based on gas chromatography ion mobility spectrometry”
  118. Corrigendum to “Mechanical properties, elastic moduli, transmission factors, and gamma-ray-shielding performances of Bi2O3–P2O5–B2O3–V2O5 quaternary glass system”
  119. Erratum
  120. Erratum to “Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies”
  121. Special Issue on Applied Biochemistry and Biotechnology (ABB 2021)
  122. Study of solidification and stabilization of heavy metals by passivators in heavy metal-contaminated soil
  123. Human health risk assessment and distribution of VOCs in a chemical site, Weinan, China
  124. Preparation and characterization of Sparassis latifolia β-glucan microcapsules
  125. Special Issue on the Conference of Energy, Fuels, Environment 2020
  126. Improving the thermal performance of existing buildings in light of the requirements of the EU directive 2010/31/EU in Poland
  127. Special Issue on Ethnobotanical, Phytochemical and Biological Investigation of Medicinal Plants
  128. Study of plant resources with ethnomedicinal relevance from district Bagh, Azad Jammu and Kashmir, Pakistan
  129. Studies on the chemical composition of plants used in traditional medicine in Congo
  130. Special Issue on Applied Chemistry in Agriculture and Food Science
  131. Strip spraying technology for precise herbicide application in carrot fields
  132. Special Issue on Pharmacology and Metabolomics of Ethnobotanical and Herbal Medicine
  133. Phytochemical profiling, antibacterial and antioxidant properties of Crocus sativus flower: A comparison between tepals and stigmas
  134. Antioxidant and antimicrobial properties of polyphenolics from Withania adpressa (Coss.) Batt. against selected drug-resistant bacterial strains
  135. Integrating network pharmacology and molecular docking to explore the potential mechanism of Xinguan No. 3 in the treatment of COVID-19
  136. Chemical composition and in vitro and in vivo biological assortment of fixed oil extracted from Ficus benghalensis L.
  137. A review of the pharmacological activities and protective effects of Inonotus obliquus triterpenoids in kidney diseases
  138. Ethnopharmacological study of medicinal plants in Kastamonu province (Türkiye)
  139. Protective effects of asperuloside against cyclophosphamide-induced urotoxicity and hematotoxicity in rats
  140. Special Issue on Essential Oil, Extraction, Phytochemistry, Advances, and Application
  141. Identification of volatile compounds and antioxidant, antibacterial, and antifungal properties against drug-resistant microbes of essential oils from the leaves of Mentha rotundifolia var. apodysa Briq. (Lamiaceae)
  142. Phenolic contents, anticancer, antioxidant, and antimicrobial capacities of MeOH extract from the aerial parts of Trema orientalis plant
  143. Chemical composition and antimicrobial activity of essential oils from Mentha pulegium and Rosmarinus officinalis against multidrug-resistant microbes and their acute toxicity study
  144. Special Issue on Marine Environmental Sciences and Significance of the Multidisciplinary Approaches
  145. An insightful overview of the distribution pattern of polycyclic aromatic hydrocarbon in the marine sediments of the Red Sea
  146. Antifungal–antiproliferative norcycloartane-type triterpenes from the Red Sea green alga Tydemania expeditionis
  147. Solvent effect, dipole moment, and DFT studies of multi donor–acceptor type pyridine derivative
  148. An extensive assessment on the distribution pattern of organic contaminants in the aerosols samples in the Middle East
  149. Special Issue on 4th IC3PE
  150. Energetics of carboxylic acid–pyridine heterosynthon revisited: A computational study of intermolecular hydrogen bond domination on phenylacetic acid–nicotinamide cocrystals
  151. A review: Silver–zinc oxide nanoparticles – organoclay-reinforced chitosan bionanocomposites for food packaging
  152. Green synthesis of magnetic activated carbon from peanut shells functionalized with TiO2 photocatalyst for Batik liquid waste treatment
  153. Coagulation activity of liquid extraction of Leucaena leucocephala and Sesbania grandiflora on the removal of turbidity
  154. Hydrocracking optimization of palm oil over NiMoO4/activated carbon catalyst to produce biogasoline and kerosine
  155. Special Issue on Pharmacology and metabolomics of ethnobotanical and herbal medicine
  156. Cynarin inhibits PDGF-BB-induced proliferation and activation in hepatic stellate cells through PPARγ
  157. Special Issue on The 1st Malaysia International Conference on Nanotechnology & Catalysis (MICNC2021)
  158. Surfactant evaluation for enhanced oil recovery: Phase behavior and interfacial tension
  159. Topical Issue on phytochemicals, biological and toxicological analysis of aromatic medicinal plants
  160. Phytochemical analysis of leaves and stems of Physalis alkekengi L. (Solanaceae)
  161. Phytochemical and pharmacological profiling of Trewia nudiflora Linn. leaf extract deciphers therapeutic potentials against thrombosis, arthritis, helminths, and insects
  162. Pergularia tomentosa coupled with selenium nanoparticles salvaged lead acetate-induced redox imbalance, inflammation, apoptosis, and disruption of neurotransmission in rats’ brain
  163. Protective effect of Allium atroviolaceum-synthesized SeNPs on aluminum-induced brain damage in mice
  164. Mechanism study of Cordyceps sinensis alleviates renal ischemia–reperfusion injury
  165. Plant-derived bisbenzylisoquinoline alkaloid tetrandrine prevents human podocyte injury by regulating the miR-150-5p/NPHS1 axis
  166. Network pharmacology combined with molecular docking to explore the anti-osteoporosis mechanisms of β-ecdysone derived from medicinal plants
  167. Chinese medicinal plant Polygonum cuspidatum ameliorates silicosis via suppressing the Wnt/β-catenin pathway
  168. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part I
  169. Investigation of improved optical and conductivity properties of poly(methyl methacrylate)–MXenes (PMMA–MXenes) nanocomposite thin films for optoelectronic applications
  170. Special Issue on Applied Biochemistry and Biotechnology (ABB 2022)
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https://doi.org/10.1515/chem-2022-0130
Keywords for this article
de-tert-butylcalix[4]arene; (1S)-(+)-10-camphorsulfonyl chloride; synthesis; chiral resolution; ECD
Creative Commons
BY 4.0

Articles in the same Issue

  1. Regular Articles
  2. Photocatalytic degradation of Rhodamine B in aqueous phase by bimetallic metal-organic framework M/Fe-MOF (M = Co, Cu, and Mg)
  3. Assessment of using electronic portal imaging device for analysing bolus material utilised in radiation therapy
  4. A detailed investigation on highly dense CuZr bulk metallic glasses for shielding purposes
  5. Simulation of gamma-ray shielding properties for materials of medical interest
  6. Environmental impact assesment regulation applications and their analysis in Turkey
  7. Sample age effect on parameters of dynamic nuclear polarization in certain difluorobenzen isomers/MC800 asphaltene suspensions
  8. Passenger demand forecasting for railway systems
  9. Design of a Robust sliding mode controller for bioreactor cultures in overflow metabolism via an interdisciplinary approach
  10. Gamma, neutron, and heavy charged ion shielding properties of Er3+-doped and Sm3+-doped zinc borate glasses
  11. Bridging chiral de-tert-butylcalix[4]arenes: Optical resolution based on column chromatography and structural characterization
  12. Petrology and geochemistry of multiphase post-granitic dikes: A case study from the Gabal Serbal area, Southwestern Sinai, Egypt
  13. Comparison of the yield and purity of plasma exosomes extracted by ultracentrifugation, precipitation, and membrane-based approaches
  14. Bioactive triterpenoids from Indonesian medicinal plant Syzygium aqueum
  15. Investigation of the effects of machining parameters on surface integrity in micromachining
  16. The mesoporous aluminosilicate application as support for bifunctional catalysts for n-hexadecane hydroconversion
  17. Gamma-ray shielding properties of Nd2O3-added iron–boron–phosphate-based composites
  18. Numerical investigation on perforated sheet metals under tension loading
  19. Statistical analysis on the radiological assessment and geochemical studies of granite rocks in the north of Um Taghir area, Eastern Desert, Egypt
  20. Two new polypodane-type bicyclic triterpenoids from mastic
  21. Structural, physical, and mechanical properties of the TiO2 added hydroxyapatite composites
  22. Tribological properties and characterization of borided Co–Mg alloys
  23. Studies on Anemone nemorosa L. extracts; polyphenols profile, antioxidant activity, and effects on Caco-2 cells by in vitro and in silico studies
  24. Mechanical properties, elastic moduli, transmission factors, and gamma-ray-shielding performances of Bi2O3–P2O5–B2O3–V2O5 quaternary glass system
  25. Cyclic connectivity index of bipolar fuzzy incidence graph
  26. The role of passage numbers of donor cells in the development of Arabian Oryx – Cow interspecific somatic cell nuclear transfer embryos
  27. Mechanical property evaluation of tellurite–germanate glasses and comparison of their radiation-shielding characteristics using EPICS2017 to other glass systems
  28. Molecular screening of ionic liquids for CO2 absorption and molecular dynamic simulation
  29. Microwave-assisted preparation of Ag/Fe magnetic biochar from clivia leaves for adsorbing daptomycin antibiotics
  30. Iminodisuccinic acid enhances antioxidant and mineral element accumulation in young leaves of Ziziphus jujuba
  31. Cytotoxic activity of guaiane-type sesquiterpene lactone (deoxycynaropicrin) isolated from the leaves of Centaurothamnus maximus
  32. Effects of welding parameters on the angular distortion of welded steel plates
  33. Simulation of a reactor considering the Stamicarbon, Snamprogetti, and Toyo patents for obtaining urea
  34. Effect of different ramie (Boehmeria nivea L. Gaud) cultivars on the adsorption of heavy metal ions cadmium and lead in the remediation of contaminated farmland soils
  35. Impact of a live bacterial-based direct-fed microbial (DFM) postpartum and weaning system on performance, mortality, and health of Najdi lambs
  36. Anti-tumor effect of liposomes containing extracted Murrayafoline A against liver cancer cells in 2D and 3D cultured models
  37. Physicochemical properties and some mineral concentration of milk samples from different animals and altitudes
  38. Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies
  39. Diagnostic and therapeutic radioisotopes in nuclear medicine: Determination of gamma-ray transmission factors and safety competencies of high-dense and transparent glassy shields
  40. Calculation of NaI(Tl) detector efficiency using 226Ra, 232Th, and 40K radioisotopes: Three-phase Monte Carlo simulation study
  41. Isolation and identification of unstable components from Caesalpinia sappan by high-speed counter-current chromatography combined with preparative high-performance liquid chromatography
  42. Quantification of biomarkers and evaluation of antioxidant, anti-inflammatory, and cytotoxicity properties of Dodonaea viscosa grown in Saudi Arabia using HPTLC technique
  43. Characterization of the elastic modulus of ceramic–metal composites with physical and mechanical properties by ultrasonic technique
  44. GC-MS analysis of Vespa velutina auraria Smith and its anti-inflammatory and antioxidant activities in vitro
  45. Texturing of nanocoatings for surface acoustic wave-based sensors for volatile organic compounds
  46. Insights into the molecular basis of some chalcone analogues as potential inhibitors of Leishmania donovani: An integrated in silico and in vitro study
  47. (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity
  48. On the relative extraction rates of colour compounds and caffeine during brewing, an investigation of tea over time and temperature
  49. Characterization of egg shell powder-doped ceramic–metal composites
  50. Rapeseed oil-based hippurate amide nanocomposite coating material for anticorrosive and antibacterial applications
  51. Chemically modified Teucrium polium (Lamiaceae) plant act as an effective adsorbent tool for potassium permanganate (KMnO4) in wastewater remediation
  52. Efficiency analysis of photovoltaic systems installed in different geographical locations
  53. Risk prioritization model driven by success factor in the light of multicriteria decision making
  54. Theoretical investigations on the excited-state intramolecular proton transfer in the solvated 2-hydroxy-1-naphthaldehyde carbohydrazone
  55. Mechanical and gamma-ray shielding examinations of Bi2O3–PbO–CdO–B2O3 glass system
  56. Machine learning-based forecasting of potability of drinking water through adaptive boosting model
  57. The potential effect of the Rumex vesicarius water seeds extract treatment on mice before and during pregnancy on the serum enzymes and the histology of kidney and liver
  58. Impact of benzimidazole functional groups on the n-doping properties of benzimidazole derivatives
  59. Extraction of red pigment from Chinese jujube peel and the antioxidant activity of the pigment extracts
  60. Flexural strength and thermal properties of carbon black nanoparticle reinforced epoxy composites obtained from waste tires
  61. A focusing study on radioprotective and antioxidant effects of Annona muricata leaf extract in the circulation and liver tissue: Clinical and experimental studies
  62. Clinical comprehensive and experimental assessment of the radioprotective effect of Annona muricata leaf extract to prevent cellular damage in the ileum tissue
  63. Effect of WC content on ultrasonic properties, thermal and electrical conductivity of WC–Co–Ni–Cr composites
  64. Influence of various class cleaning agents for prosthesis on Co–Cr alloy surface
  65. The synthesis of nanocellulose-based nanocomposites for the effective removal of hexavalent chromium ions from aqueous solution
  66. Study on the influence of physical interlayers on the remaining oil production under different development modes
  67. Optimized linear regression control of DC motor under various disturbances
  68. Influence of different sample preparation strategies on hypothesis-driven shotgun proteomic analysis of human saliva
  69. Determination of flow distance of the fluid metal due to fluidity in ductile iron casting by artificial neural networks approach
  70. Investigation of mechanical activation effect on high-volume natural pozzolanic cements
  71. In vitro: Anti-coccidia activity of Calotropis procera leaf extract on Eimeria papillata oocysts sporulation and sporozoite
  72. Determination of oil composition of cowpea (Vigna unguiculata L.) seeds under influence of organic fertilizer forms
  73. Activated partial thromboplastin time maybe associated with the prognosis of papillary thyroid carcinoma
  74. Treatment of rat brain ischemia model by NSCs-polymer scaffold transplantation
  75. Lead and cadmium removal with native yeast from coastal wetlands
  76. Characterization of electroless Ni-coated Fe–Co composite using powder metallurgy
  77. Ferrate synthesis using NaOCl and its application for dye removal
  78. Antioxidant, antidiabetic, and anticholinesterase potential of Chenopodium murale L. extracts using in vitro and in vivo approaches
  79. Study on essential oil, antioxidant activity, anti-human prostate cancer effects, and induction of apoptosis by Equisetum arvense
  80. Experimental study on turning machine with permanent magnetic cutting tool
  81. Numerical simulation and mathematical modeling of the casting process for pearlitic spheroidal graphite cast iron
  82. Design, synthesis, and cytotoxicity evaluation of novel thiophene, pyrimidine, pyridazine, and pyridine: Griseofulvin heterocyclic extension derivatives
  83. Isolation and identification of promising antibiotic-producing bacteria
  84. Ultrasonic-induced reversible blood–brain barrier opening: Safety evaluation into the cellular level
  85. Evaluation of phytochemical and antioxidant potential of various extracts from traditionally used medicinal plants of Pakistan
  86. Effect of calcium lactate in standard diet on selected markers of oxidative stress and inflammation in ovariectomized rats
  87. Identification of crucial salivary proteins/genes and pathways involved in pathogenesis of temporomandibular disorders
  88. Zirconium-modified attapulgite was used for removing of Cr(vi) in aqueous solution
  89. The stress distribution of different types of restorative materials in primary molar
  90. Reducing surface heat loss in steam boilers
  91. Deformation behavior and formability of friction stir processed DP600 steel
  92. Synthesis and characterization of bismuth oxide/commercial activated carbon composite for battery anode
  93. Phytochemical analysis of Ziziphus jujube leaf at different foliar ages based on widely targeted metabolomics
  94. Effects of in ovo injection of black cumin (Nigella sativa) extract on hatching performance of broiler eggs
  95. Separation and evaluation of potential antioxidant, analgesic, and anti-inflammatory activities of limonene-rich essential oils from Citrus sinensis (L.)
  96. Bioactivity of a polyhydroxy gorgostane steroid from Xenia umbellata
  97. BiCAM-based automated scoring system for digital logic circuit diagrams
  98. Analysis of standard systems with solar monitoring systems
  99. Structural and spectroscopic properties of voriconazole and fluconazole – Experimental and theoretical studies
  100. New plant resistance inducers based on polyamines
  101. Experimental investigation of single-lap bolted and bolted/bonded (hybrid) joints of polymeric plates
  102. Investigation of inlet air pressure and evaporative cooling of four different cogeneration cycles
  103. Review Articles
  104. Comprehensive review on synthesis, physicochemical properties, and application of activated carbon from the Arecaceae plants for enhanced wastewater treatment
  105. Research progress on speciation analysis of arsenic in traditional Chinese medicine
  106. Recent modified air-assisted liquid–liquid microextraction applications for medicines and organic compounds in various samples: A review
  107. An insight on Vietnamese bio-waste materials as activated carbon precursors for multiple applications in environmental protection
  108. Antimicrobial activities of the extracts and secondary metabolites from Clausena genus – A review
  109. Bioremediation of organic/heavy metal contaminants by mixed cultures of microorganisms: A review
  110. Sonodynamic therapy for breast cancer: A literature review
  111. Recent progress of amino acid transporters as a novel antitumor target
  112. Aconitum coreanum Rapaics: Botany, traditional uses, phytochemistry, pharmacology, and toxicology
  113. Corrigendum
  114. Corrigendum to “Petrology and geochemistry of multiphase post-granitic dikes: A case study from the Gabal Serbal area, Southwestern Sinai, Egypt”
  115. Corrigendum to “Design of a Robust sliding mode controller for bioreactor cultures in overflow metabolism via an interdisciplinary approach”
  116. Corrigendum to “Statistical analysis on the radiological assessment and geochemical studies of granite rocks in the north of Um Taghir area, Eastern Desert, Egypt”
  117. Corrigendum to “Aroma components of tobacco powder from different producing areas based on gas chromatography ion mobility spectrometry”
  118. Corrigendum to “Mechanical properties, elastic moduli, transmission factors, and gamma-ray-shielding performances of Bi2O3–P2O5–B2O3–V2O5 quaternary glass system”
  119. Erratum
  120. Erratum to “Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies”
  121. Special Issue on Applied Biochemistry and Biotechnology (ABB 2021)
  122. Study of solidification and stabilization of heavy metals by passivators in heavy metal-contaminated soil
  123. Human health risk assessment and distribution of VOCs in a chemical site, Weinan, China
  124. Preparation and characterization of Sparassis latifolia β-glucan microcapsules
  125. Special Issue on the Conference of Energy, Fuels, Environment 2020
  126. Improving the thermal performance of existing buildings in light of the requirements of the EU directive 2010/31/EU in Poland
  127. Special Issue on Ethnobotanical, Phytochemical and Biological Investigation of Medicinal Plants
  128. Study of plant resources with ethnomedicinal relevance from district Bagh, Azad Jammu and Kashmir, Pakistan
  129. Studies on the chemical composition of plants used in traditional medicine in Congo
  130. Special Issue on Applied Chemistry in Agriculture and Food Science
  131. Strip spraying technology for precise herbicide application in carrot fields
  132. Special Issue on Pharmacology and Metabolomics of Ethnobotanical and Herbal Medicine
  133. Phytochemical profiling, antibacterial and antioxidant properties of Crocus sativus flower: A comparison between tepals and stigmas
  134. Antioxidant and antimicrobial properties of polyphenolics from Withania adpressa (Coss.) Batt. against selected drug-resistant bacterial strains
  135. Integrating network pharmacology and molecular docking to explore the potential mechanism of Xinguan No. 3 in the treatment of COVID-19
  136. Chemical composition and in vitro and in vivo biological assortment of fixed oil extracted from Ficus benghalensis L.
  137. A review of the pharmacological activities and protective effects of Inonotus obliquus triterpenoids in kidney diseases
  138. Ethnopharmacological study of medicinal plants in Kastamonu province (Türkiye)
  139. Protective effects of asperuloside against cyclophosphamide-induced urotoxicity and hematotoxicity in rats
  140. Special Issue on Essential Oil, Extraction, Phytochemistry, Advances, and Application
  141. Identification of volatile compounds and antioxidant, antibacterial, and antifungal properties against drug-resistant microbes of essential oils from the leaves of Mentha rotundifolia var. apodysa Briq. (Lamiaceae)
  142. Phenolic contents, anticancer, antioxidant, and antimicrobial capacities of MeOH extract from the aerial parts of Trema orientalis plant
  143. Chemical composition and antimicrobial activity of essential oils from Mentha pulegium and Rosmarinus officinalis against multidrug-resistant microbes and their acute toxicity study
  144. Special Issue on Marine Environmental Sciences and Significance of the Multidisciplinary Approaches
  145. An insightful overview of the distribution pattern of polycyclic aromatic hydrocarbon in the marine sediments of the Red Sea
  146. Antifungal–antiproliferative norcycloartane-type triterpenes from the Red Sea green alga Tydemania expeditionis
  147. Solvent effect, dipole moment, and DFT studies of multi donor–acceptor type pyridine derivative
  148. An extensive assessment on the distribution pattern of organic contaminants in the aerosols samples in the Middle East
  149. Special Issue on 4th IC3PE
  150. Energetics of carboxylic acid–pyridine heterosynthon revisited: A computational study of intermolecular hydrogen bond domination on phenylacetic acid–nicotinamide cocrystals
  151. A review: Silver–zinc oxide nanoparticles – organoclay-reinforced chitosan bionanocomposites for food packaging
  152. Green synthesis of magnetic activated carbon from peanut shells functionalized with TiO2 photocatalyst for Batik liquid waste treatment
  153. Coagulation activity of liquid extraction of Leucaena leucocephala and Sesbania grandiflora on the removal of turbidity
  154. Hydrocracking optimization of palm oil over NiMoO4/activated carbon catalyst to produce biogasoline and kerosine
  155. Special Issue on Pharmacology and metabolomics of ethnobotanical and herbal medicine
  156. Cynarin inhibits PDGF-BB-induced proliferation and activation in hepatic stellate cells through PPARγ
  157. Special Issue on The 1st Malaysia International Conference on Nanotechnology & Catalysis (MICNC2021)
  158. Surfactant evaluation for enhanced oil recovery: Phase behavior and interfacial tension
  159. Topical Issue on phytochemicals, biological and toxicological analysis of aromatic medicinal plants
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