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One-pot green synthesis, biological evaluation, and in silico study of pyrazole derivatives obtained from chalcones

  • Emma Ghazaryan , Armen Karapetyan EMAIL logo , Yana Gharibyan , Tigran Gharibyan , Asya Vorskanyan , Siranush Harutyunyan , Margarita Dovlatyan , Aleksandr Yengoyan and Tiruhi Gomktsyan
Published/Copyright: November 11, 2024
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Green Processing and Synthesis
From the journal Green Processing and Synthesis Volume 13 Issue 1

Abstract

Several chalcones and their pyrazole derivatives have been synthesized using traditional methods under microwave (MW) and ultrasonic (US) irradiation. The latter were synthesized using US-assisted and MW-assisted one-pot techniques. The use of this technology led to a reduction in reaction time and energy consumption, as well as an increase in the yield of the final products, which means more efficient synthesis. An in silico study was conducted and the plant growth-stimulating effects of the synthesized compounds were revealed. To study the growth-regulating activity of the synthesized compounds, a study of aqueous suspensions at a concentration of 50 and 25 mg·L−1 was carried out on the viability, germination, and growth of seeds.

Graphical abstract

Keywords: green chemistry; MW-assisted; US-assisted synthesis; chalcone; pyrazole

1 Introduction

The chemical modification of functionally substituted chalcones has great and still not fully disclosed potential prospects. It still attracted the increased attention of numerous researchers, which is reflected in the annually increasing number of publications in high-ranking journals [1,2,3,4,5,6,7,8]. Currently, a wide range of schemes is available for the synthesis of various chalcone analogs. A series of derivatives with various heterocycles was synthesized using chalcones. In some cases, green energy sources are used for the synthesis of chalcones when the molecules are activated under ultrasonic [9,10,11,12,13,14,15,16] or microwave [17,18,19,20,21,22,23] irradiation.

Chalcones and their derivatives exhibit a wide range of biological activities. Among these, compounds with anti-inflammatory [24,25,26,27,28], anticancer [29,30,31,32,33,34], antimalarial [35,36], antiviral [37,38], antimicrobial [9,17,18,39,40,41,42], antioxidant [43,44,45,46], anti-diabetic [47,48,49], anticonvulsant [50], antihypertensive [51,52], antileishmanial [53,54], analgesic [28], antihistaminic [55], and anti-Alzheimer [56] activities have been discovered.

Over the last decade, one-pot synthesis techniques have been increasingly used [57,58,59,60,61,62,63]. One-pot synthesis is a strategy for increasing the efficiency of a chemical reaction in which reactants are added sequentially one at a time without intermediate treatment. This is highly desirable for chemists because eliminating the time-consuming process of separating and purifying chemical intermediates can save time and resources. The sequential synthesis in one container is also called telescopic synthesis. However, these syntheses are performed under ordinary conditions, most often with heat.

In connection with the above, the final goal of this study was the one-pot synthesis of pyrazole derivatives of chalcones. For this purpose, environmentally friendly ultrasound and microwave methods were used, which results were compared with conventional synthetic methods. The synthesized compounds were examined for their biological properties.

2 Materials and methods

2.1 General

Microwave (MW)-assisted syntheses were performed on a MAS-II Plus microwave synthesis workstation (SINEO) with a maximum irradiation power of 1,000 W. An ultrasonic generator I10-840 with an operating frequency of 22 kHz ± 10% and a maximal pulse power of 1,000 W was used for the sonochemical synthesis. Before carrying out the necessary syntheses with MW and ultrasonic (US) irradiations, a lot of works were done to optimize the experimental conditions. The irradiation power and reaction time were changed. Based on this, the following conditions were applied in all experiments: irradiation power of 30% (300 W) at boiling and exposure time of 30 min.

The structure and purity of the synthesized compounds were confirmed by 1H and 13C NMR spectra obtained at 30°C on a Varian Mercury-300 NMR spectrometer (300 and 75 MHz, respectively) in a mixture of CCl4/DMSO-d6 solvents (3:1), using a standard pulse sequence and TMS as an internal standard. The progress of the reactions and purity of the obtained compounds were checked by TLC on Silufol UV-254 plates using an acetone/hexane mixture (2:1 or 1:1) as the eluent. Elemental analysis was performed using a Eurovector EA3000 CHN analyzer. Melting points were determined using a Stuart SMP10 apparatus and uncorrected.

2.2 Conventional, MW-assisted, and US-assisted synthesis of chalcones 1a–1m were carried out in a similar way

To a solution of 0.001 mol of substituted aldehyde in 10 mL of methanol, 0.001 mol of substituted acetophenone and 10 mL of 5% NaOH solution were slowly added. The mixture was boiled for 4 h at a temperature of 80–85°C (or irradiated for 30 min at a temperature of 80–85°C) and left overnight. The precipitate that formed was filtered, thoroughly washed with water, and dried. The resulting chalcones were recrystallized from ether. The 1H and 13C NMR spectral parameters, as well as the elemental analysis data for chalcones 1a–1m synthesized by all three methods, are very similar. The files were stored in the Zenodo Repository doi: 10.5281/zenodo.11108499.

2.3 One-pot conventional and MW-assisted synthesis of pyrazole derivatives 2a–2n were carried out in a similar way

A solution of 0.001 mol of substituted aldehyde and 0.001 mol of substituted acetophenone in 10 mL of methanol and 10 mL of a 5% NaOH solution was boiled for 4 h (or irradiated for 30 min at a temperature – 80–85°C) and left overnight at room temperature. The next day, 0.004 mol of phenylhydrazine was added and heated at a temperature – 80−85°C for 14−15 h (or irradiated for 30 min at a temperature – 80−85°C). The resulting precipitate was filtered, thoroughly washed with water, dried, and purified by boiling it in hexane. 1H and 13C NMR spectra and elemental analysis data for pyrazole derivatives 2a–2n are given in the Zenodo Repository doi: 10.5281/zenodo.11108499.

3 Results

The synthesis plan was as follows: (1) chalcone synthesis using the conventional method under the influence of MW irradiation and US irradiation and (2) one-pot conventional, US-assisted, and MW-assisted synthesis of pyrazole derivatives.

In the first stage, 13 chalcones (1a–m) were prepared by Claisen–Schmidt condensation between substituted benzaldehydes and acetophenones. Then, by reacting these chalcones with phenylhydrazine, the one-pot synthesis of pyrazole derivatives was carried out both by the conventional method and under the influence of microwave and ultrasonic irradiation according to a well-known route (Scheme 1).

Scheme 1 Synthesis of chalcones and corresponding pyrazole derivatives.
Scheme 1

Synthesis of chalcones and corresponding pyrazole derivatives.

Most synthesized compounds have been described in the literature. The novelty of this study lies in the one-pot synthesis of pyrazole derivatives of chalcones, both by the traditional method and under the influence of US and MW irradiations, and a comparative analysis of the results of these methods. A comparative analysis of the physicochemical characteristics of these compounds is presented in Tables 1 and 2, respectively.

Table 1

Comparison of physicochemical characteristics of chalcone 1 obtained by the conventional method and under the influence of MW and US irradiations

No R R1 Conventional (5% NaOH) MW-assisted* (2.5% NaOH) US-assisted* (2.5% NaOH)
Yield (%) mp (°C) Reaction time (h) Yield (%) mp (°C) Yield (%) mp (°C)
1a H H 99 52 4.5 90 52 99 53
1b Cl H 95 112 4.5 95 111 80 112
1c Cl Cl 99 156 4.5 90 156 86 156
1d Cl Br 87 167 4.5 79 167 84 167
1e Cl CH3 94 151 4.5 88 151 76 152
1f N(Me)2 Br 42 140 4.5 41 140 54 140
1g Br Br 90 186 4.5 94 186 82 186
1h OCH3 CH3 83 100 4.5 76 100 72 100
1i OCH3 Cl 83 121 4.5 93 120 84 121
1j OCH3 Br 94 146 4.5 91 146 62 146
1k Cl OCH3 95 132 4.5 82 132 79 132
1l Br OCH3 97 154 4.5 87 154 96 154
1m OCH3 OCH3 93 103 4.5 95 103 96 103

*Reaction times are 0.5 h.

Table 2

Comparison of physicochemical characteristics of pyrazole derivatives 2 synthesized by the conventional and MW-assisted methods using one-pot methodology

No R R1 Conventional (5% NaOH) MW-assisted* (2.5% NaOH)
Yield (%) mp (°C) Reaction time (h) Yield (%) mp (°C)
2a H H 36 129 18 42 130
2b Cl H 41 130 18 50 130
2c Cl Cl 32 150 18 41 150
2d Cl Br 36 176 18 47 176
2e Cl CH3 29 146 18 35 146
2f N(CH3)2 Br 51 185 18 55 185
2g Br Br 42 185 18 34 185
2h OCH3 CH3 26 146 18 45 146
2i OCH3 Cl 30 160 18 40 161
2j OCH3 Br 53 176 18 50 176
2k Cl OCH3 22 147 18 38 146
2l Br OCH3 27 143 18 31 143
2m OCH3 OCH3 46 134 18 51 135
2n Br OCH3 32 101 18 42 101

*Reaction time: 2 h (1 h at each stage).

In the MW-assisted one-pot synthesis of pyrazole derivatives, the reaction time was reduced by nine times compared to the traditional methods, and the product yields increased (Table 2).

However, in experiments with US irradiation, the yields of the final products were low; therefore, this method is not recommended for the synthesis of pyrazole derivatives, and Table 2 shows only the MW-assisted data.

As expected, chalcones 1a–m were in the sterically preferred E form (Scheme 2a). This is evidenced by the value of the vicinal spin–spin interaction constant between olefin protons: 15.4–15.7 Hz, corresponding to their mutual trans-orientation.

Scheme 2 The structure of chalcones (a) and their pyrazole derivatives (b).
Scheme 2

The structure of chalcones (a) and their pyrazole derivatives (b).

In the 1H NMR spectra of pyrazole derivatives, in addition to the geminal spin-spin interaction constant between the protons of the methylene group (17.1–17.3 Hz), interaction constants of these protons with the methine proton are observed equally to 12.2 and 6.9 Hz, corresponding to trans and gauche orientations, which indicates the equatorial location of the Ar group (Scheme 2b).

3.1 Plant growth-stimulating properties of the synthesized compounds

The obtained compounds were subjected to laboratory vegetation tests to determine their herbicidal, fungicidal, and growth-regulatory properties. Almost all the compounds obtained showed a stimulating effect on plant growth.

The experiments were carried out on the seeds and seedlings of common beans (Phaseolus vulgaris L.). The effects of aqueous suspensions of compounds 1,2 at concentrations of 50 and 25 mg·L−1 on seed viability, germination, and seedling growth were studied. These data were compared with the effects of pure water solutions of the same concentration. All data are presented in Table 3.

Table 3

Plant growth stimulatory activity of compounds 1,2 compared with pure water solutions, which activity was taken as 100%

No Activity (%) No Activity (%) No Activity (%) No Activity (%)
Concentration Concentration Concentration Concentration
50 mg·L−1 25 mg·L−1 50 mg·L−1 25 mg·L−1 50 mg·L−1 25 mg·L−1 50 mg·L−1 25 mg·L−1
1a 43 64 1h 74 85 2b 80 127 2i 83 66
1b 46 86 1i 73 54 2c 85 80 2j 110 134
1c 100 100 1j 63 126 2d 77 62 2k 154 137
1d 85 93 1k 83 66 2e 88 52 2l 88 96
1e 58 99 1l 60 49 2f 81 128 2m 100 117
1f 79 97 1m 75 72 2g 78 111 2n 85 73
1g 78 60 2a 80 132 2h 78 75

The activity of the tested compounds varied between 43 and 154% compared to water solutions, with an activity of 100%. In some cases (1a, 1b, 1d, 1e, 1f, 1h, 1j and 2a, 2b, 2f, 2g, 2j, 2l, 2m), the growth-stimulating effect of solutions with a lower concentration (25 mg·L−1) was higher than that of the more concentrated (50 mg·L−1) solutions. Compounds that showed activity above 100% in the experiment were selected for further study and field trials using solutions with concentrations less than 25 mg·L−1.

3.2 In silico study

3.2.1 Calculation of ADMET properties and biological activity

Physicochemical and pharmacokinetic values and a prediction of the possible toxicity of substances were calculated using the online platforms SwissADME [64] and ADMETlab v 2.0 [65]. Based on PASSonline, data on the possible therapeutic effects of the resulting substances were obtained [66].

The synthesized compounds complied with Lipinski’s rule, as the molar mass of the resulting compounds did not exceed 500 g·mol−1 and the number of hydrogen atoms capable of forming donor and acceptor hydrogen bonds did not exceed five (Table 4).

Table 4

Physicochemical values of the synthesized compounds 2

No Physicochemical properties Pharmacokinetics Druglikeness Medicinal chemistry
Molar mass (g·mol−1) Num. heavy atoms Num. H-bond acceptors Num. H-bond donors GI absorption BBB permeant Log Kp (skin permeation) (cm·s−1) Lipinski Bioavailability score Leadlikeness Synthetic accessibility
2a 298.38 23 1 0 H Yes −4.56 Yes 0.55 No 3.36
2b 332.83 24 1 0 H Yes −4.32 Yes 0.55 No 3.37
2c 367.27 25 1 0 H Yes −4.08 Yes 0.55 No 3.38
2d 411.72 25 1 0 H Yes −4.31 Yes 0.55 No 3.43
2e 346.85 25 1 0 H Yes −4.14 Yes 0.55 No 3.48
2f 420.34 27 1 0 H Yes −4.72 Yes 0.55 No 3.72
2g 456.17 25 1 0 H Yes −4.54 Yes 0.55 No 3.44
2h 342.43 26 2 0 H Yes −4.58 Yes 0.55 No 3.52
2i 362.85 26 2 0 H Yes −4.52 Yes 0.55 No 3.43
2j 407.30 26 2 0 H Yes −4.74 Yes 0.55 No 3.48
2k 362.85 26 2 0 H Yes −4.52 Yes 0.55 No 3.44
2l 407.30 26 2 0 H Yes −4.74 Yes 0.55 No 3.48
2m 358.43 27 3 0 H Yes −4.96 Yes 0.55 No 3.57
2n 421.33 27 2 0 H Yes −4.88 Yes 0.55 No 3.60

The tested compounds showed high absorption through the gastrointestinal tract (GIT) and blood–brain barrier (BBB) (Figure 1).

Figure 1 Map of compounds passing through the gastrointestinal tract and BBB based on lipophilicity and topological index of the polar surface of the studied compounds. BBB – passage through the BBB, HIA – passage through the gastrointestinal tract, PGP + active transport, PGP – passive transport.
Figure 1

Map of compounds passing through the gastrointestinal tract and BBB based on lipophilicity and topological index of the polar surface of the studied compounds. BBB – passage through the BBB, HIA – passage through the gastrointestinal tract, PGP + active transport, PGP – passive transport.

These substances are divided into three clusters with similar properties (1, 2, and 3). In some cases, there is an almost complete coincidence of these compounds within one cluster.

Toxicity studies showed that none of the compounds had toxic effects on the skin and eyes, and all compounds, except two, had mutagenic and carcinogenic properties. None of the compounds exhibited any hepatotoxicity (Table 5).

Table 5

Predicted toxicity of tested compounds

No Carcinogenicity AMES toxicity Irritant effect Rat oral acute toxicity Hepatotoxicity
Eyes Skin
2a Yes Yes No No No No
2b Yes Yes No No No No
2c Yes Yes No No Yes No
2d Yes No No No Yes No
2e Yes Yes No No No No
2f Yes Yes No No Yes No
2g No No No No Yes No
2h Yes Yes No No No No
2i Yes Yes No No No No
2j Yes No No No Yes No
2k Yes Yes No No No No
2l Yes No No No Yes No
2m Yes Yes No No No No
2n No No No No Yes No

Using PASSonline, it was shown that the resulting substituted pyrazoles, depending on the substituent, exhibited similar therapeutic activity. All the substances showed fairly high activity (above average). Based on their therapeutic effects, these substances were divided into four groups (Table 6).

Table 6

Data on possible therapeutic activity of the studied compounds

Top activity
Possible therapeutic effect No Pa/Pi
5-O-(4-Coumaroyl)-d-quinate 3′-monooxygenase inhibitor 2a 0.84/0.004
2b 0.886/0.003
2d 0.800/0.008
2k 0.762/0.012
2e 0.849/0.004
2i 0.762/0.012
2c 0.886/0.003
Antiobesity 2g 0.737/0.005
(S)-6-Hydroxynicotine oxidase inhibitor 2f 0.697/0.007
Aspulvinone dimethylallyltransferase inhibitor 2j 0.810/0.031
2l 0.810/0.031
2h 0.707/0.061
2m 0.795/0.035
2n 0.786/0.038

4 Conclusions

Thus, it has been established that the microwave- and ultrasonic-assisted synthesis of chalcones can be carried out in high yields and with much less time than when synthesizing them using conventional methods. When synthesizing pyrazole derivatives based on chalcones using the one-pot methodology, good product yields were achieved and the reaction times were significantly reduced, which contributed to energy savings.

The synthesized pyrazole derivatives exhibited pronounced growth-stimulating activity. The study showed that the synthesized compounds freely pass through the GIT and the BBB do not have a toxic effect on the skin and eyes and presumably have inhibitory activity against obesity, 5-O-(4-coumaroyl)-d-quinate 3′-monooxygenase, (S)-6-hydroxynicotine oxidase, and aspulvinone dimethylallyltransferase.

  1. Funding information: This work was supported by the State Committee for Science of the Ministry of Education and Science of the Republic of Armenia under the framework of Scientific Project No. 21T-1D165.

  2. Author contributions: Tiruhi Gomktsyan and Emma Ghazaryan: conceptualization, data curation, validation, investigation, visualization, and methodology; Yana Gharibyan and Tigran Gharibyan: resources, software, formal analysis, visualization, and methodology; Armen Karapetyan and Asya Vorskanyan: resources, data curation, formal analysis, validation, investigation, visualization, and methodology; Siranush Harutyunyan and Margarita Dovlatyan: analysis of growth stimulator activity, investigation, and visualization; and Aleksandr Yengoyan: conceptualization, supervision, validation, investigation, methodology, writing – original draft, project administration, writing – review, and editing.

  3. Conflict of interest: The authors state no conflict of interest.

  4. Data availability statement: The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request, and NMR spectral data are presented in the supplementary material and in the Zenodo repository.

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Received: 2024-05-14
Accepted: 2024-08-29
Published Online: 2024-11-11

© 2024 the author(s), published by De Gruyter

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

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https://doi.org/10.1515/gps-2024-0105
Keywords for this article
green chemistry; MW-assisted; US-assisted synthesis; chalcone; pyrazole
Creative Commons
BY 4.0

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  53. Immobilisation of catalase purified from mushroom (Hydnum repandum) onto glutaraldehyde-activated chitosan and characterisation: Its application for the removal of hydrogen peroxide from artificial wastewater
  54. Sodium titanium oxide/zinc oxide (STO/ZnO) photocomposites for efficient dye degradation applications
  55. Effect of ex situ, eco-friendly ZnONPs incorporating green synthesised Moringa oleifera leaf extract in enhancing biochemical and molecular aspects of Vicia faba L. under salt stress
  56. Biosynthesis and characterization of selenium and silver nanoparticles using Trichoderma viride filtrate and their impact on Culex pipiens
  57. Photocatalytic degradation of organic dyes and biological potentials of biogenic zinc oxide nanoparticles synthesized using the polar extract of Cyperus scariosus R.Br. (Cyperaceae)
  58. Assessment of antiproliferative activity of green-synthesized nickel oxide nanoparticles against glioblastoma cells using Terminalia chebula
  59. Chlorine-free synthesis of phosphinic derivatives by change in the P-function
  60. Anticancer, antioxidant, and antimicrobial activities of nanoemulsions based on water-in-olive oil and loaded on biogenic silver nanoparticles
  61. Study and mechanism of formation of phosphorus production waste in Kazakhstan
  62. Synthesis and stabilization of anatase form of biomimetic TiO2 nanoparticles for enhancing anti-tumor potential
  63. Microwave-supported one-pot reaction for the synthesis of 5-alkyl/arylidene-2-(morpholin/thiomorpholin-4-yl)-1,3-thiazol-4(5H)-one derivatives over MgO solid base
  64. Screening the phytochemicals in Perilla leaves and phytosynthesis of bioactive silver nanoparticles for potential antioxidant and wound-healing application
  65. Graphene oxide/chitosan/manganese/folic acid-brucine functionalized nanocomposites show anticancer activity against liver cancer cells
  66. Nature of serpentinite interactions with low-concentration sulfuric acid solutions
  67. Multi-objective statistical optimisation utilising response surface methodology to predict engine performance using biofuels from waste plastic oil in CRDi engines
  68. Microwave-assisted extraction of acetosolv lignin from sugarcane bagasse and electrospinning of lignin/PEO nanofibres for carbon fibre production
  69. Biosynthesis, characterization, and investigation of cytotoxic activities of selenium nanoparticles utilizing Limosilactobacillus fermentum
  70. Highly photocatalytic materials based on the decoration of poly(O-chloroaniline) with molybdenum trichalcogenide oxide for green hydrogen generation from Red Sea water
  71. Highly efficient oil–water separation using superhydrophobic cellulose aerogels derived from corn straw
  72. Beta-cyclodextrin–Phyllanthus emblica emulsion for zinc oxide nanoparticles: Characteristics and photocatalysis
  73. Assessment of antimicrobial activity and methyl orange dye removal by Klebsiella pneumoniae-mediated silver nanoparticles
  74. Influential eradication of resistant Salmonella Typhimurium using bioactive nanocomposites from chitosan and radish seed-synthesized nanoselenium
  75. Antimicrobial activities and neuroprotective potential for Alzheimer’s disease of pure, Mn, Co, and Al-doped ZnO ultra-small nanoparticles
  76. Green synthesis of silver nanoparticles from Bauhinia variegata and their biological applications
  77. Synthesis and optimization of long-chain fatty acids via the oxidation of long-chain fatty alcohols
  78. Eminent Red Sea water hydrogen generation via a Pb(ii)-iodide/poly(1H-pyrrole) nanocomposite photocathode
  79. Green synthesis and effective genistein production by fungal β-glucosidase immobilized on Al2O3 nanocrystals synthesized in Cajanus cajan L. (Millsp.) leaf extracts
  80. Green stability-indicating RP-HPTLC technique for determining croconazole hydrochloride
  81. Green synthesis of La2O3–LaPO4 nanocomposites using Charybdis natator for DNA binding, cytotoxic, catalytic, and luminescence applications
  82. Eco-friendly drugs induce cellular changes in colistin-resistant bacteria
  83. Tangerine fruit peel extract mediated biogenic synthesized silver nanoparticles and their potential antimicrobial, antioxidant, and cytotoxic assessments
  84. Green synthesis on performance characteristics of a direct injection diesel engine using sandbox seed oil
  85. A highly sensitive β-AKBA-Ag-based fluorescent “turn off” chemosensor for rapid detection of abamectin in tomatoes
  86. Green synthesis and physical characterization of zinc oxide nanoparticles (ZnO NPs) derived from the methanol extract of Euphorbia dracunculoides Lam. (Euphorbiaceae) with enhanced biosafe applications
  87. Detection of morphine and data processing using surface plasmon resonance imaging sensor
  88. Effects of nanoparticles on the anaerobic digestion properties of sulfamethoxazole-containing chicken manure and analysis of bio-enzymes
  89. Bromic acid-thiourea synergistic leaching of sulfide gold ore
  90. Green chemistry approach to synthesize titanium dioxide nanoparticles using Fagonia Cretica extract, novel strategy for developing antimicrobial and antidiabetic therapies
  91. Green synthesis and effective utilization of biogenic Al2O3-nanocoupled fungal lipase in the resolution of active homochiral 2-octanol and its immobilization via aluminium oxide nanoparticles
  92. Eco-friendly RP-HPLC approach for simultaneously estimating the promising combination of pentoxifylline and simvastatin in therapeutic potential for breast cancer: Appraisal of greenness, whiteness, and Box–Behnken design
  93. Use of a humidity adsorbent derived from cockleshell waste in Thai fried fish crackers (Keropok)
  94. One-pot green synthesis, biological evaluation, and in silico study of pyrazole derivatives obtained from chalcones
  95. Bio-sorption of methylene blue and production of biofuel by brown alga Cystoseira sp. collected from Neom region, Kingdom of Saudi Arabia
  96. Synthesis of motexafin gadolinium: A promising radiosensitizer and imaging agent for cancer therapy
  97. The impact of varying sizes of silver nanoparticles on the induction of cellular damage in Klebsiella pneumoniae involving diverse mechanisms
  98. Microwave-assisted green synthesis, characterization, and in vitro antibacterial activity of NiO nanoparticles obtained from lemon peel extract
  99. Rhus microphylla-mediated biosynthesis of copper oxide nanoparticles for enhanced antibacterial and antibiofilm efficacy
  100. Harnessing trichalcogenide–molybdenum(vi) sulfide and molybdenum(vi) oxide within poly(1-amino-2-mercaptobenzene) frameworks as a photocathode for sustainable green hydrogen production from seawater without sacrificial agents
  101. Magnetically recyclable Fe3O4@SiO2 supported phosphonium ionic liquids for efficient and sustainable transformation of CO2 into oxazolidinones
  102. A comparative study of Fagonia arabica fabricated silver sulfide nanoparticles (Ag2S) and silver nanoparticles (AgNPs) with distinct antimicrobial, anticancer, and antioxidant properties
  103. Visible light photocatalytic degradation and biological activities of Aegle marmelos-mediated cerium oxide nanoparticles
  104. Physical intrinsic characteristics of spheroidal particles in coal gasification fine slag
  105. Exploring the effect of tea dust magnetic biochar on agricultural crops grown in polycyclic aromatic hydrocarbon contaminated soil
  106. Crosslinked chitosan-modified ultrafiltration membranes for efficient surface water treatment and enhanced anti-fouling performances
  107. Study on adsorption characteristics of biochars and their modified biochars for removal of organic dyes from aqueous solution
  108. Zein polymer nanocarrier for Ocimum basilicum var. purpurascens extract: Potential biomedical use
  109. Green synthesis, characterization, and in vitro and in vivo biological screening of iron oxide nanoparticles (Fe3O4) generated with hydroalcoholic extract of aerial parts of Euphorbia milii
  110. Novel microwave-based green approach for the synthesis of dual-loaded cyclodextrin nanosponges: Characterization, pharmacodynamics, and pharmacokinetics evaluation
  111. Bi2O3–BiOCl/poly-m-methyl aniline nanocomposite thin film for broad-spectrum light-sensing
  112. Green synthesis and characterization of CuO/ZnO nanocomposite using Musa acuminata leaf extract for cytotoxic studies on colorectal cancer cells (HCC2998)
  113. Review Articles
  114. Materials-based drug delivery approaches: Recent advances and future perspectives
  115. A review of thermal treatment for bamboo and its composites
  116. An overview of the role of nanoherbicides in tackling challenges of weed management in wheat: A novel approach
  117. An updated review on carbon nanomaterials: Types, synthesis, functionalization and applications, degradation and toxicity
  118. Special Issue: Emerging green nanomaterials for sustainable waste management and biomedical applications
  119. Green synthesis of silver nanoparticles using mature-pseudostem extracts of Alpinia nigra and their bioactivities
  120. Special Issue: New insights into nanopythotechnology: current trends and future prospects
  121. Green synthesis of FeO nanoparticles from coffee and its application for antibacterial, antifungal, and anti-oxidation activity
  122. Dye degradation activity of biogenically synthesized Cu/Fe/Ag trimetallic nanoparticles
  123. Special Issue: Composites and green composites
  124. Recent trends and advancements in the utilization of green composites and polymeric nanocarriers for enhancing food quality and sustainable processing
  125. Retraction
  126. Retraction of “Biosynthesis and characterization of silver nanoparticles from Cedrela toona leaf extracts: An exploration into their antibacterial, anticancer, and antioxidant potential”
  127. Retraction of “Photocatalytic degradation of organic dyes and biological potentials of biogenic zinc oxide nanoparticles synthesized using the polar extract of Cyperus scariosus R.Br. (Cyperaceae)”
  128. Retraction to “Green synthesis on performance characteristics of a direct injection diesel engine using sandbox seed oil”
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