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Efficient synthesis, X-ray diffraction study and antimicrobial activity of some novel thiazolidin-4-ones and perhydro-1,3-thiazin-4-ones

  • Deepika Gautam , Poonam Gautam and Ram P. Chaudhary EMAIL logo
Published/Copyright: February 19, 2013
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Heterocyclic Communications
From the journal Heterocyclic Communications Volume 19 Issue 1

Abstract

Condensations of thiosemicarbazones 1 derived from 1-tetralones with chloroacetic acid and 2-bromopropionic acid in the presence of N-methylpyridinium p-toluenesulfonate (an ionic liquid) yield the corresponding 2-substituted 4-thiazolidinones 2. The reactions of 1 with 3-chloropropionic acid afford perhydro-1,3-thiazinan-4-ones 3 in excellent yields. The structures of compounds 2 and 3 were established on the basis of elemental analysis, IR, NMR and mass spectral data. X-Ray crystallographic studies of compound 2a are reported. Compounds 1–3 were investigated for antimicrobial activities against Bacillus subtilis, Staphylococcus aureus (Gram-positive bacteria) and Pseudomonas aeruginosa, Escherichia coli (Gram-negative bacteria) and the fungi Aspergillus niger, Candida albicans and Aspergillus fumigatus. Thiazolidin-4-ones were found to be more active than perhydrothiazin-4-ones.

Keywords: antimicrobial activities; ionic liquid; perhydro-1,3-thiazin-4-ones; 4-thiazolidinones; thiosemicarbazones

Introduction

4-Thiazolidinones and perhydro-1,3-thiazin-4-ones have been exploited in the past few decades for their wide range of biological activities such as antifungal, anticonvulsant [1], anti-HIV [2], analgesic, diuretic, antiviral, antiprotozoal [3], antibacterial [4, 5], anticancer [6], anti-inflammatory [7–9], cytotoxic [10], antitumor [11] and antituberculosis [12–14] properties. Recently, 4-thiazolidinones have been considered as a new class of antidiabetic drugs and potent aldose reductase inhibitors. They also have potential for treating diabetic complications such as nephropathy, neuropathy and cataract [15]. Several methods for preparation of 4-thiazolidinones have been reported in the literature. The commonly employed methods involve either a one-pot, three-component cyclocondensation of amines, carbonyl compounds and mercaptoacetic acid, or a two-step synthesis of Schiff base intermediates followed by their cyclocondensation with mercaptoacetic acid. The reported methods involve hazardous solvents and a long reaction time of 10–20 h with moderate to poor yields. There are reports of using N,N′-dicyclohexylcarbodiimide (DCC) [16], anhydrous ZnCl2 [17, 18], Dean-Stark apparatus and molecular sieves for removal of water from the reaction mixture. In continuation of our work on the search for environmental friendly methods of synthesis of 4-thiazolidinones [19, 20], we now report a two-component cyclocondensation of thiosemicarbazones with halo acids yielding 2,5-disubstituted 4-thiazolidinones and perhydro-1,3-thiazin-4-ones under solvent-free conditions (Scheme 1).

Scheme 1 Reagents and conditions: (a) ClCH2COOH or CH3CH(Br)COOH, NaOAc, anhydrous EtOH; (b) ClCH2COOH, CH3CH(Br)COOH, N-methylpyridinium p-toluenesulfonate; (c) Cl(CH2)2COOH, NaOAc, AcOH, Ac2O; (d) Cl(CH2)2COOH, N-methylpyridinium p-toluenesulfonate.
Scheme 1

Reagents and conditions: (a) ClCH2COOH or CH3CH(Br)COOH, NaOAc, anhydrous EtOH; (b) ClCH2COOH, CH3CH(Br)COOH, N-methylpyridinium p-toluenesulfonate; (c) Cl(CH2)2COOH, NaOAc, AcOH, Ac2O; (d) Cl(CH2)2COOH, N-methylpyridinium p-toluenesulfonate.

Results and discussion

The synthesis and spectral characterization of compound 2a, obtained by reaction of 1a with chloroacetic acid, by conventional and solvent-free methods was reported [19] earlier by our group. In this paper, we report the X-ray crystallographic studies of compound 2a (Figure 1). Compound 2a crystallizes in the triclinic system having space group P-1 with the following parameters: a = 7.7239(13) Å, b = 8.746(2) Å, c = 11.1093(19) Å, α = 103.801(17)°, β = 95.285(14)°, γ = 116.05(2)°. The crystallographic data of compound 2a are reported in Table 1. The CIF file of compound 2a has been deposited with the Cambridge Structural Database and CCDC, no. 885668. The selected bond lengths and bond angles of 2a are reported in Table 2.

Figure 1 ORTEP drawing indicating molecular structure and atomic labeling of the (Z)-2-[(E)-(3,4-dihydronaphthalen-1(2H)ylidene)hydrazono]-thiazolidin-4-one (2a).
Figure 1

ORTEP drawing indicating molecular structure and atomic labeling of the (Z)-2-[(E)-(3,4-dihydronaphthalen-1(2H)ylidene)hydrazono]-thiazolidin-4-one (2a).

Table 1

Crystal data and structure refinement of (Z)-2-[(E)-(3,4-dihydronaphthalen-1(2H)ylidene)hydrazono]-thiazolidin-4-one (2a).

CCDC no.885668
Empirical formulaC13H13N3OS
Formula weight259.32
Temperature (K)293 (2)
Wavelength (Å)0.71073
Crystal systemTriclinic
Space groupP-1
Unit cell dimensions
 a (Å)7.7239(13)
 b (Å)8.746(2)
 c (Å)11.1093(19)
 α (°)103.801(17)
 β (°)95.285(14)
 γ (°)116.05(2)
 Volume (Å3)637.9(2)
 Z2
Density (calculated) (mg/m3)1.340
Absorption coefficient (mm-1)0.244
Crystal size (mm3)0.28 × 0.26 × 0.18
Theta range for data collection2.8994–29.0408
Reflections collected2813
Independent reflections2344
Data/restraints/parameters2813/0/165
Goodness-of-fit on F21.118
Final R indices [I > 2σ(I) = 2591 data]R1 = 0.1272, wR2 = 0.1943
R indices (all data)R1 = 0.0651, wR2 = 0.1868
Largest diff. peak and hole (eÅ-3)-0.441, 0.822
Table 2

Selected geometrical parameters of (Z)-2-[(E)-(3,4-dihydronaphthalen-1(2H)ylidene)hydrazono]-thiazolidin-4-one (2a).

EntryBond length (Å)EntryBond angle (°)
S(1)-C(1)1.767(5)C(1)-S(1)-C(4)90.7(3)
S(1)-C(4)1.802(6)C(5)-N(4)-N(3)113.7(5)
N(4)-N(3)1.410(6)C(1)-N(1)-C(3)116.3(5)
N(3)-C(1)1.280(7)C(6)-N(3)-N(1)110.3(5)
C(3)-O(1)1.221(7)N(1)-C(3)-C(4)112.3(5)
C(1)-N(3)1.364(7)N(3)-C(1)-N(1)122.0(5)
C(1)-N(1)1.279(7)N(3)-C(1)-S(1)125.5(4)
C(5)-C(6)1.512(8)S(1)-C(1)-N(1)112.3(4)
C(10)-C(11)1.397(11)C(6)-C(5)-C(14)119.7(5)
C(14)-C(13)1.503(10)C(5)-C(14)-C(13)120.9(5)

The reaction of 1-tetralone with thiosemicarbazide in ethanol containing a catalytic amount of hydrochloric acid gave hydrazinecarbothioamide 1a. Heating of 1a under reflux with 2-bromopropionic acid in the presence of anhydrous sodium acetate in absolute ethanol for 12 h gave 2c (Scheme 1) in 56% yield (conventional method). Compound 2c was obtained in 78% yield by cyclocondensation of 1a with 2-bromopropionic acid in the presence of an ionic liquid, N-methylpyridinium p-toluenesulfonate, at 100°C for 4 h (Table 3). The analog 2d was similarly prepared by adopting the procedure for 2c. The structures of 2c,d were established by elemental analysis and spectral (IR, NMR and mass) data.

Table 3

Synthesis of 4-thiazolidinones 2a–d and perhydro-1,3-thiazinan-4-ones 3a–b by conventional and solvent-free methods.

CompoundSolvent-free methodConventional method
Reaction time (h)Yield (%)Reaction time (h)Yield (%)
2a2.590 [19]563
2b2.588 [19]564
2c`781256
2d4761256
3a6751448
3b6741444

Heating of compound 1a under reflux with 3-chloropropionic acid in the presence of anhydrous sodium acetate and acetic anhydride in glacial acetic acid for 14 h furnished product 3a in 48% yield (conventional method). Compound 3a was obtained in 75% yield under solvent-free conditions using an ionic liquid (Table 3). The analog 3b was obtained in a similar way. The structures of 3a,b were established by elemental analysis and spectral data. The time of reaction and yields for the formation of compounds 2 and 3 by conventional methods as well as by solvent-free methods are reported in Table 3. The ionic liquid, N-methylpyridinium p-toluenesulfonate, was synthesized according to the literature [21]. The recovery of the ionic liquid was also attempted and it was found that it can be reused in two more cycles.

Antimicrobial studies

The antimicrobial screening of the synthesized compounds 2a–d and 3a,b was carried out using the disc diffusion method [22] by measuring the zone of inhibition. All compounds were screened in vitro for their antimicrobial activity against bacteria Bacillus subtilis, Staphylococcus aureus (Gram-positive bacteria) and Pseudomonas aeruginosa and Escherichia coli (Gram-negative bacteria) and fungi Aspergillus niger, Candida albicans and Aspergillus fumigatus at 40 μg/mL concentration. The standard drug, ampicillin trihydrate, was used for comparison purposes. Compounds 2a, 2c and 2d showed the highest activity against Gram-positive bacteria B. subtilis and S. aureus. Compounds 2b, 3a and 3b exhibited mild to moderate antibacterial activity in terms of the zone of inhibition (Table 4). Compounds 2a–d and 3a,b were also screened for antifungal activity and the results are reported in Table 5.

Table 4

Antibacterial activity of 4-thiazolidinones 2a–d and perhydro-1,3-thiazin-4-ones 3a,b.

CompoundZone of inhibition (mm)
Gram-positiveGram-negative
B. subtilisS. aureusP. aeruginosaE. coli
2a22231819
2b16151214
2c18191718
2d17161617
3a14121011
3b12131211
Ampicillin trihydrate26282421
DMSO0000
Table 5

Antifungal activity of 4-thiazolidinones 2a–d and perhydro-1,3-thiazin-4-ones 3a,b.

CompoundZone of inhibition (mm)
A. nigerC. albicansA. fumigates
2a181517
2b111214
2c161717
2d201918
3a161316
3b131413
Ampicillin trihydrate242522
DMSO000

Conclusion

A convenient and efficient method for the synthesis of 2-substituted 4-thiazolidinones and perhydro-1,3-thiazin-4-ones under solvent-free conditions using ionic liquid is reported. The reaction times are markedly reduced and the yields of the products are greater in comparison to the classical procedure. Thazolidine-4-ones were found to be more active than perhydro-1,3-thiazinan-4-ones as antimicrobial agents.

Experimental

All chemicals were obtained from Sigma and used without further purification. Melting points were determined in open capillaries and are uncorrected. Elemental analysis was done on a Carlo-Erba 1108 elemental analyzer. Mass spectra were recorded on TOF MS ES+ 2.44e 4 instrument. 1H NMR (400 MHz) and 13C NMR (100 MHz) spectra were recorded on a Bruker Avance II 400 NMR spectrometer using tetramethylsilane (TMS) as internal standard. IR spectra were recorded on an ABB FTIR spectrometer. Thin layer chromatography (TLC) was performed on silica gel G-coated plates using iodine vapor as visualizing agent. General procedures for synthesis of compounds 1a,b and 2a,b have been previously reported by our group [19]. X-Ray diffraction analysis was performed on an X Calibur EOS Oxford diffractometer. Compound 2a [19] was crystallized from ethyl acetate by the slow evaporation method to obtain a pale yellow crystal for single crystal X-ray diffraction studies.

Synthesis of N-methylpyridinium p-toluenesulfonate (ionic liquid)

Pyridine (0.55 mol) was added to methyl p-toluenesulfonate (0.5 mol) at 0–10°C and the mixture was stirred at room temperature for 1 h. The resultant solid of N-methylpyridinium p-toluenesulfonate was filtered, washed with ethyl acetate to remove unreacted substrates and dried. The physical parameters of the ionic liquid were in good agreement with those reported in the literature [21].

Solvent-free procedure for synthesis of 2

A mixture of 1 (0.025 mol), 2-bromopropionic acid (3.8 g, 0.025 mol) and the ionic liquid (2.0 g) was stirred at 100°C for 4 h. After the reaction was completed, as monitored by TLC, the mixture was poured into ice-cold water. The resultant precipitate of 2 was filtered, dried and crystallized from ethanol (Table 3).

Conventional procedure for synthesis of 2

A mixture of 1 (0.015 mol), 2-bromopropionic acid (2.3 g, 0.015 mol), anhydrous sodium acetate (2.46 g, 0.03 mol) and absolute ethanol (5 mL) was heated under reflux for 10 h. The mixture was cooled to room temperature and then poured into ice-cold water. The separated solid was filtered, washed with water and crystallized from ethanol (Table 3).

2-{(E)-[3,4-Dihydro-2H-naphthalen-(1E)-ylidene]-hydrazono}-5-methylthiazolidin-4-one (2c)

Mp 158–160°C; IR: ν 3132 (NH), 1713 (N-C=O), 1612 cm-1 (C=N); 1H NMR (CDCl3): δ 1.68 (d, 3H, CH3, J = 7 Hz), 1.90 (m, 2H, CH2), 2.81 (t, 2H, CH2, J = 6 Hz), 2.89 (t, 2H, CH2, J = 7 Hz), 4.06 (q, 1H, SCH, J = 7 Hz), 7.15 (d, 1H, ArH, J = 7 Hz), 7.23 (d, 1H, ArH, J = 7 Hz), 7.30 (t, 1H, ArH, J = 7 Hz), 8.21 (dd, 1H, ArH, J = 7 Hz, J = 1 Hz); 13C NMR (CDCl3): δ 175.9 (C=O), 162.2 (C=N), 140.9, 132.12, 130.25, 128.7, 126.4, 125.5 (ArC), 42.5 (SCH), 29.8 (CH2), 27.5 (CH2), 22.1 (CH2), 19.1 (CH3); MS: m/z 274 (M+H+, 100%). Anal. Calcd for C14H15N3SO: C, 61.53; H, 5.49; N, 15.38; S, 11.72. Found: C, 61.58; H, 5.60; N, 15.49; S, 11.83.

2-{(E)-[6-Methoxy-3,4-dihydronaphthalen-1(2H)-ylidene]-hydrazono}-5-methyl-thiazolidin-4-one (2d)

Mp 172–174°C; IR: ν 3070 (NH), 1705 (N-C=O), 1597 cm-1 (C=N); 1H NMR (DMSO-d6): δ 1.58 (d, 3H, CH3, J = 7 Hz), 1.87 (t, 2H, CH2, J = 6 Hz), 2.80 (m, 4H, 2CH2), 3.81 (s, 3H, OCH3), 3.99 (q, 1H, SCH, J = 7 Hz), 6.66 (s, 1H, ArH), 6.75 (d, 1H, ArH, J = 9 Hz), 8.08 (d, 1H, ArH, J = 9 Hz); 13C NMR (DMSO-d6): δ 181.7 (C=O), 165.5 (C=N), 164.9 (C-OCH3), 147.2, 131.7, 130.1, 117.9, 117.3 (ArC), 60.0 (OCH3), 34.9 (SCH), 34.9 (CH2), 32.0 (CH2), 27.0 (CH2), 24.1 (CH3); MS: m/z 304 (M+H+, 100%). Anal. Calcd for C15H17N3O2S: C, 59.40; H, 5.61; N, 13.86; S, 10.56. Found: C, 59.49; H, 5.69; N, 13.91; S, 10.86.

Solvent-free procedure for synthesis of 3

An equimolar mixture of 1 (0.025 mol) and 3-chloropropionic acid (2.71 g, 0.025 mol) and the ionic liquid (2.0 g) was stirred at 100°C for 6 h. After the reaction was completed, as monitored by TLC, the mixture was poured into ice-cold water. The resultant precipitate of 3 was filtered, dried and crystallized from ethanol (Table 3).

Conventional procedure for synthesis of 3

A mixture of 1 (0.005 mol), 3-chloropropionic acid (0.54 g, 0.005 mol), anhydrous sodium acetate (0.8 g, 0.010 mol), glacial acetic acid (3.0 mL) and acetic anhydride (1.0 mL) was heated under reflux for 10–14 h. The mixture was cooled to room temperature and poured into ice-cold water. The gummy product obtained was extracted with ethyl acetate (2 × 25 mL). The extract was washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The solid residue of 3 was crystallized from ethyl acetate.

2-{(E)-[3,4-Dihydronaphthalene-1(2H)-ylidene]hydrazono}-perhydro-1,3-thiazin-4-one (3a)

Mp 154–156°C; IR: ν 1697 (N-C=O) 1589 (C=N), 1543 cm-1 (C=C); 1H NMR (CDCl3): δ 1.89 (m, 2H, CH2), 2.79–3.07 (m, 8H, 4CH2), 7.15 (t, 1H, ArH, J = 7 Hz), 7.21–7.34 (m, 2H, ArH), 8.24 (dd, 1H, ArH, J = 7 Hz, J = 2 Hz), 9.72 (br, 1H, NH exchangeable with D2O); 13C NMR (CDCl3): δ 169.4 (C=O), 162.4 (C=N), 140.9, 132.5, 130.3, 128.8, 126.3, 125.4 (ArC), 34.3 (SCH2), 29.9, 27.4, 23.2, 22.7, 22.1 (CH2); MS: m/z 274 (M+H)+ (20), 233 (34), 231 (100%). Anal. Calcd for C14H15N3SO: C, 61.53; H, 5.49; N, 15.38; S, 11.72. Found: C, 61.45; H, 5.44; N, 15.32; S, 11.80.

2-{(E)-[6-Methoxy-3,4-dihydronaphthalen-1(2H)-ylidene]hydrazono}-perhydro-1,3-thiazin-4-one (3b)

Mp 139–140°C; IR: ν 1697 (N-C=O), 1589 (C=N), 1551 cm-1 (C=C); 1H NMR (CDCl3): δ 1.85–2.17 (m, 2H, CH2), 2.76–3.16 (m, 6H, 3CH2), 3.83 (s, 3H, OCH3), 6.65 (m, 1H, ArH), 6.78–6.81 (dd, 1H, ArH, J = 6 Hz, J = 3 Hz), 8.17 (m, 1H, ArH), 9.74 (br, 1H, NH exchangeable with D2O); 13C NMR (CDCl3): δ 169.5 (C=O), 162.6 (C=N), 140.8, 132.1, 130.1, 127.2, 125.1, 123.4 (ArC), 58.9 (OCH3), 33.4 (SCH2), 28.9, 27.2, 23.1, 22.4, 22.6 (CH2); MS: m/z 304 (M+H)+ (20%). Anal. Calcd for C15H17N3O2S: C, 59.40; H, 5.61; N, 13.86; S, 10.56. Found: C, 59.33; H, 5.56; N, 13.78; S, 10.45.

Corresponding author: Ram P. Chaudhary, Department of Chemistry, Sant Longowal Institute of Engineering and Technology, Longowal (Sangrur), Punjab 148106, India

The authorities of Sant Longowal Institute of Engineering and Technology, Longowal, India are gratefully acknowledged for providing the research facilities.

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Received: 2012-12-20
Accepted: 2012-12-28
Published Online: 2013-02-19
Published in Print: 2013-03-01

©2013 by Walter de Gruyter Berlin Boston

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  12. A simple and efficient synthesis of novel naphthyridine-1-H-pyrazole-4-carboxylic acid esters/carbaldehydes using Vilsmeier-Haack reagent
  13. Melamine-formaldehyde resin supported H+-catalyzed three-component synthesis of 1,8-dioxo-decahydroacridine derivatives in water and under solvent-free conditions
  14. A simple and efficient procedure for synthesis of symmetrical bis(4-amino-4H-1,2,4-triazole-5-thiols)
  15. Poly(ethylene)glycol/AlCl3 as a new and efficient system for multicomponent Biginelli-type synthesis of pyrimidinone derivatives
  16. Synthesis, crystal structure, and bioactivity of N-dichloroacetyl diazabicyclo compounds
https://doi.org/10.1515/hc-2012-0180
Keywords for this article
antimicrobial activities; ionic liquid; perhydro-1,3-thiazin-4-ones; 4-thiazolidinones; thiosemicarbazones
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Articles in the same Issue

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  2. Masthead
  3. Reviews
  4. Synthesis and applications of benzothiazole containing cyanine dyes
  5. Synthesis and chemistry of structurally unique hexasubstituted pyrazolines
  6. Research Articles
  7. Synthesis and characterization of heteroarylthio derivatives of 5,17-di-tert-butyl-11,23-diamido-25, 27-diprotected calix[4]arene
  8. New heterocyclic chalcones. Part 6. Synthesis and cytotoxic activities of 5- or 6-(3-aryl- 2-propenoyl)-2(3H)-benzoxazolones
  9. Novel benzofuran derivatives: synthesis and antitumor activity
  10. Synthesis, characterization and in vitro antimicrobial assessment of some novel 4H-1, 4-benzothiazines and their sulfone derivatives
  11. Efficient synthesis, X-ray diffraction study and antimicrobial activity of some novel thiazolidin-4-ones and perhydro-1,3-thiazin-4-ones
  12. A simple and efficient synthesis of novel naphthyridine-1-H-pyrazole-4-carboxylic acid esters/carbaldehydes using Vilsmeier-Haack reagent
  13. Melamine-formaldehyde resin supported H+-catalyzed three-component synthesis of 1,8-dioxo-decahydroacridine derivatives in water and under solvent-free conditions
  14. A simple and efficient procedure for synthesis of symmetrical bis(4-amino-4H-1,2,4-triazole-5-thiols)
  15. Poly(ethylene)glycol/AlCl3 as a new and efficient system for multicomponent Biginelli-type synthesis of pyrimidinone derivatives
  16. Synthesis, crystal structure, and bioactivity of N-dichloroacetyl diazabicyclo compounds
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