Baker’s yeast catalyzed one-pot synthesis of bioactive 2-[benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acids

Anusaya S. Chavan; Arun S. Kharat; Manisha R. Bhosle; Ramrao A. Mane

doi:10.1515/hc-2017-0130

Article Open Access

Baker’s yeast catalyzed one-pot synthesis of bioactive 2-[benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acids

Anusaya S. Chavan , Arun S. Kharat , Manisha R. Bhosle and Ramrao A. Mane

Published/Copyright: March 21, 2018

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From the journal Heterocyclic Communications Volume 24 Issue 2

Abstract

An efficient and simple one-pot protocol has been developed for synthesis of substituted derivatives of 2-hydrazono-4-thiazolidinone-5-acetic acids 4a–j and 6a–g by cyclocondensation of aryl/pyrazolyl aldehyde, thiosemicarbazide and maleic anhydride in acetonitrile in the presence of readily available whole cell biocatalyst, baker’s yeast (Saccharomyces cerevisiae). The reaction is enhanced by ultrasonication.

Keywords: baker’s yeast; 2-hydrazono-4-thiazolidinon-5-yl-acetic acids; one-pot multicomponent reaction; ultrasonication

Introduction

Thiazolidinone ring system is a core component of penicillins and cephalosporins and many derivatives display a wide spectrum of therapeutic activities [1] including antibacterial [2], [3], anti-inflammatory [4], [5], anticancer [6], [7], [8], [9], antitubercular [10], anticonvulsant [11], analgesic [12], antimicrobial [12], [13], [14], [15], and COX-2 inhibitory properties [16]. 1,3-Thiazolidine-2,4-dione is an essential component of clinical antidiabetic agents ciglitazone and pioglitazone and others bioactive compounds [17], [18], [19], [20] (Figure 1). In search for an efficient antidiabetic agent, chemists are paying attention to synthesis of new 1,3-thiazolidin-4-ones developing efficient synthetic protocols. Due to the therapeutic significance of hydrazono-4-thiazolidinone derivatives, several protocols have been reported [17], [18], [19], [20], [21] for their synthesis. A two-step synthesis is usually used for obtaining 2-hydrazono-4-thiazolidinone-5-acetic acids starting from aldehydes [18], [19]. The aldehyde is condensed with thiosemicarbazide and the resultant thiosemicarbazone is then allowed to react with maleic anhydride by thia-Michael addition to furnish the desired hydrazonothiazolidinone. Many hydrazonothiazolidinones have been prepared by carrying one-pot tandem cyclocondensation of aldehyde, maleic acid and thiosemicarbazide in toluene in the presence of p-toluenesulfonic acid as catalyst under microwave assisted irradiation at 100–120°C [18]. Hydrazonothiazolidinone acetic acids with a pyrazolyl scaffold have been synthesized in a similar manner starting from a pyrazolecarbaldehyde [17].

Figure 1

Selected bioactive agents with a thiazolidine-2,4-dione scaffold.

Enzymes are well explored as biocatalysts. Baker’s yeast, one of the widely used whole cell source of biocatalysts [22], [23], [24] has been used to aid Hantzsch dihydropyridine synthesis [25], synthesis of polyhydroquinoline [26], Biginelli reaction for synthesis of dihydropyrimidinones [27], aldol condensation and Knoevenagel condensation [28]. It has been reported that biocatalysts display their catalytic behavior even in organic solvents, making way to easy solubilization of organic substrates [29], [30], [31], [32], [33].

Considering the information discussed above and in continuation of our earlier work on biocatalysis [28], [34], [35], [36], [37], [38], in this report we describe the use of activated baker’s yeast as a source of a biocatalyst for accelerating the synthesis of substituted 2-hydrazono-4-thiazolidinone-5-acetic acids [17], [18], [19], [20], [21]. This report described an improved approach to the synthesis of the desired products.

Results and discussion

A one-pot multi-component cyclocondensation protocol was developed for synthesis of aryl-substituted 2-hydrazono-4-thiazolidine-1,3-one-5-acetic acids 4a–j (Scheme 1) and pyrazol-4-yl substituted analogs 6a–g (Scheme 2). The cornerstone of this work was finding that baker’s yeast catalyzes these preparations. Initially, the cyclocondensation of benzaldehyde (1a), thiosemicarbazide (2) and maleic anhydride (3) in ethanol was run as a two-step model reaction. In the first step, a mixture of benzaldehyde and thiosemicarbazide was stirred in ethanol at room temperature in the presence of baker’s yeast for 4 h to furnish the intermediate thiosemicarbazone in 76% yield. Then the intermediate thiosemicarbazone was allowed to react with maleic anhydride in ethanol in the presence of yeast at room temperature. This treatment gave the desired product 4a in 65% yield after 48 h. It was found that both steps are catalyzed by baker’s yeast. This finding prompted us to undertake cyclocondensation leading to 4a by the reaction of benzaldehyde (1a), thiosemicarbazide (2) and maleic anhydride (3) in ethanol in the presence of baker’s yeast at room temperature as a one-step procedure. This reaction furnished the desired product 4a after 48 h with an enhanced yield of 70%.

Scheme 1

Synthesis of compounds 4a–j.

Scheme 2

Synthesis of compounds 6a–f.

The use of ultrasonication for organic transformations is well explored [37]. The ultrasonication is also used for disruption of the biological cells for the release of their interiors [39], [40], [41]. In this work, ultrasonication was used to disrupt baker’s yeast cells for the release of intracellular enzymes that catalyze the reaction. The use of ultrasonication at room temperature resulted in a remarkable decrease of the reaction time from 48 h to 4 h. Interestingly, an attempted reaction under ultrasonication but in the absence of baker’s yeast did not produce any product 4a even after 40 h.

The model reaction was also screened using different solvents and varying the temperature. It was found that the reaction is best conducted in acetonitrile at room temperature. The optimized conditions are given in Experimental. Overall, products 4a–j (Scheme 1) were obtained under the optimized conditions in the yields varying from 82% to 93%. In a similar way, the pyrazole analogs 6a–g (Scheme 2) were synthesized in the yields of 71%–96%.

Conclusion

An alternative environmentally friendly baker’s yeast-catalyzed synthetic route to known 2-hydrazono-1,3-thiazolidin-4-ones-5-carboxylic acids 4a–j and 6a–g was developed. Sonication-assisted disruption of the baker’s yeast cell wall provides the intracellular enzymes that catalyze the reaction. The synthesis is operationally simple, is conducted at room temperature, and the desired product is obtained in short reaction time and with high yield.

Experimental

Melting points were determined in an open capillary tube and are uncorrected. ¹³C NMR spectra were recorded in DMSO-d₆ on a Bruker AvIII HD-300 spectrometer operating at 75 MHz. The purity of products was checked by TLC using silica gel-coated aluminum sheets, and visualization was accomplished by treatment with iodine or exposure to ultraviolet light. The ultrasonication-assisted reactions were carried out in a Bandelin Sonorexbath reactor operating at a frequency of 35 kHz and a nominal power of 200 W.

General procedure for synthesis of compounds 4a–j

A mixture of baker’s yeast (1 g) and acetonitrile (15 mL) was sonicated at 35 kHz at room temperature for 30 min. After addition of a benzaldehyde 1a–j or a pyrazol-4-carbaldehyde 5a–f (5 mmol), thiosemicarbzide (5.5 mmol) and maleic anhydride (5.5 mmol) the mixture was stirred at room temperature for an additional 3.5 h. The progress of the reaction was monitored by thin layer chromatography on silica gel using ethyl acetate/petroleum ether (2:8) as eluent. The mixture was treated with ethyl acetate (30 mL), filtered through a pad of Celite (1 g), and the filtrate was concentrated under reduced pressure. The residue of product 4a–j was crystallized from ethanol. The mp’s and spectral data for all compounds 4a–j are virtually identical with those reported previously [1], [2].

2-(N-Benzylidenehydrazono)-1,3-thiazolidin-4-one-5-acetic acid (4a)

Yield 93%; off-white powder; mp 252–254°C; ¹³C NMR: δ 36.7, 43.6, 127.7, 128.8, 130.7, 134.2, 156.3, 164.3, 171.7, 175.5. HRMS (ESI). Calcd for C₁₂H₁₁N₃O₃S (M+H)⁺: m/z 278.0677. Found: m/z 278.0676.

2-(N-2-Nitrobenzylidene)2-hydrazono-1,3-thiazolidin-4-one-5-acetic acid (4b)

Yield 92%; pale yellow powder; mp 270–271°C; ¹³C NMR: δ 36.8, 43.7, 120.5, 127.8, 128.9, 130.7, 156.3, 164.8, 171.6, 175.6. HRMS (ESI). Calcd for C₁₂H₁₀N₄O₅S (M+H)⁺: m/z 322.0411. Found: m/z 322.0410.

2-(4-Flurobenzylidenehydrazono)-4-thiazolidinone-5-acetic acid (4c)

Yield 90%; off-white powder; mp 276–278°C; ¹³C NMR: δ 36.8, 43.6, 115.8, 116.1, 129.8, 129.9, 130.8, 130.9, 155.1, 165.2, 161.9, 171.8, 175.5. HRMS (ESI). Calcd for C₁₂H₁₀FN₃O₃S (M+H)⁺: m/z 296.0499. Found: m/z 296.0499.

2-(4-Methoxybenzylidenehydrazono)-1,3-thiazolidin-4-one-5-acetic acid (4d)

Yield 93%; off-white powder; mp 254–256°C; ¹³C NMR: δ 36.7, 43.6, 55.2, 127.6, 128.9, 130.7, 134.3, 156.3, 164.3, 171.8 and 175.4. HRMS (ESI). Calcd for C₁₃H₁₃N₃O₄S (M+H)⁺: m/z 307.1356. Found: m/z 307.1356.

2-(4-Hydroxybenzylidenehydrazono)-1,3-thiazolidin-4-one-5-carboxylic acid (4e)

Yield 85%; off-white powder; mp 255–257°C; ¹³C NMR: δ 36.7, 43.6, 126.3, 127.8, 134.3, 155.2, 164.4, 170.9 and 175.3. HRMS (ESI). Calcd for C₁₂H₁₁N₃O₄S (M+H)⁺: m/z 293.1230. Found: m/z 293.1220.

2-(4-Chlorobenzylidenehydrazono)-1,3-thiazolidin-4-one-5-acetic acid (4f)

Yield 87%; off-white powder; mp 273–274°C; ¹³C NMR: δ 36.6, 43.5, 127.6, 128.8, 131.6, 133.2, 154.3, 164.3, 171.6 and 175.5. HRMS (ESI). Calcd for C₁₂H₁₀ClN₃O₃S (M+H)⁺: m/z 311.0131. Found: m/z 311.0131.

2-(4-N,N Dimethylaminobenzylidenehydrazono)-1,3-thiazolidin- 4-one-5-acetic acid (4g)

Yield 82%; off-white powder; mp 278–279°C; ¹³C NMR: δ 36.9, 39.3, 43.6, 118.7, 119.4, 128.3, 130.7, 156.3, 164.4, 171.8, 175.5. HRMS (ESI). Calcd for C₁₄H₁₆N₄O₃S (M+H)⁺: m/z 320.0943. Found: m/z 320.0944.

2-(Cinnamylidenehydrazono)-1,3-thiazolidin-4-one-5-acetic acid (4h)

Yield 84%; white powder; mp 192–194°C; ¹³C NMR: δ 36.7, 43.5, 119.4, 127.6, 128.7, 130.7, 134.3, 138.3, 156.3, 164.3, 171.6, 175.5. HRMS (ESI). Calcd for C₁₄H₁₃N₃O₃S (M+H)⁺: m/z 304.0791. Found: m/z 304.0790.

2-(3,4-Dimethoxybenzylidene)hydrazono)-1,3-thiazolidin-4-one-5-acetic acid (4i)

Yield 90%; off-white powder; mp 232–234°C; ¹³C NMR: δ 38.4, 44.5, 56.2, 114.4, 115.4, 122.5, 127.1, 149.5, 149.9, 152.1, 177.0, 177.3. HRMS (ESI). Calcd for C₁₄H₁₅N₃O₅S (M+H)⁺: m/z 337.0732. Found: m/z 337.0732.

2-(2-Hydroxybenzylidenehydrazono)-1,3-thiazolidin-4-one-5-acetic acid (4j)

Yield 82%; off-white powder; mp 236–238°C; ¹³C NMR: δ 38.4, 44.5, 115.0, 118.2, 121.8, 130.3, 135.2, 149.5, 158.6, 163, 177.0, 177.3. HRMS (ESI). Calcd for C₁₂H₁₁N₃O₄S (M+H)⁺: m/z 293.0470. Found: m/z 293.0460.

General procedure for synthesis of compounds 6a–f

A mixture containing a pyrazole-4-carbaldehyde 5a–f and other reagents as described above in acetonitrile (20 mL) was allowed to react for 8 h. Workup was conducted as described above.

2-[(1,3-Diphenylpyrazol-4-yl)methylenehydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acid (6a)

Yield 82%; off-white powder; mp 263–265°C; ¹³C NMR: δ 36.8, 43.7, 116.7, 118.8, 127.1, 128.5 (2C), 128.6 (2C), 128.8 (2C), 129.5 (2C), 129.6, 132.0, 138.9, 149.1, 151.6, 171.7, 175.4; MS (ESI): m/z 420 (M+H)⁺. Anal. Calcd for C₂₁H₁₇N₅O₃S: C, 60.13; H, 4.09; N, 16.70; S, 7.64. Found: C, 60.33; H, 4.04; N, 16.57; S, 7.61.

2-{[1-Phenyl-3-(4-methylphenyl)pyrazol-4-yl]methylenehydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid (6b)

Yield 96%; off-white powder; mp 230–232°C; ¹³C NMR: δ 20.9, 36.8, 43.7, 116.6, 118.8, 127.0, 128.5 (2C), 129.1 (2C), 129.6 (2C), 130.8, 138.0, 138.9, 149.2, 151.7, 162.7, 166.7, 171.8, 175.4; MS (ESI): m/z 434 (M+H)⁺. Anal. Calcd for C₂₂H₁₉N₅O₃S: C, 60.96; H, 4.42; N, 16.16; S, 7.40. Found: C, 61.00; H, 4.48; N, 16.20; S, 7.35.

2-{[1-Phenyl-3-(4-methoxyphenyl)pyrazol-4-yl]methylenehydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid (6c)

Yield 80%; off-white powder; 242–243°C; ¹³C NMR: δ 36.9, 43.7, 55.2, 113.9, 114.3, 116.4, 118.8 (2C), 124.4 (2C), 126.9 (2C), 139.6, 130.0, 138.9, 149.3, 151.5, 159.6, 162.7, 171.8, 175.5; MS (ESI): m/z 450 (M+H)⁺. Anal. Calcd for C₂₂H₁₉N₅O₄S: C, 58.79; H, 4.26; N, 15.58; S, 7.13. Found: C, 58.60; H, 4.30; N, 15.52 and S, 7.20.

2-{[1-Phenyl-3-(4-flurophenyl)pyrazol-4-yl]methylenehydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid (6d)

Yield 82%; off-white powder; mp 249–250°C; ¹³C NMR: δ 36.7, 43.7, 114.2, 115.2, 115.4, 117.2 (2C), 127.1 (2C), 128.6 (2C), 129.6, 130.8, 130.9, 138.8, 150.4, 162.8, 163.5, 171.8 and 175.4; MS (ESI): m/z 438 (M+H)⁺. Anal. Calcd for C₂₁H₁₆FN₅O₃S: C, 57.66; H, 3.69; 4.34; N, 16.01; S, 7.33. Found: C, 57.60; H, 4.00; N, 16.08; S, 7.29.

2-{[1-Phenyl-3-(4-nitrophenyl)pyrazol-4-yl]methylenehydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid (6e)

Yield 78%; off-white powder; mp 260–262°C; ¹³C NMR: δ 36.7, 43.8, 117.5, 117.9, 118.7, 118.9 (2C), 123.9 (2C), 127.4 (2C), 128.9, 129.7, 131.4, 134.4, 138.8, 148.9, 163.2, 171.7 and 175.4; MS (ESI): m/z 465 (M+H)⁺. Anal. Calcd for C₂₁H₁₆N₆O₅S: C, 54.31; H, 3.47; N, 18.09; S, 6.90. Found: C, 54.60; H, 3.40; N, 18.04; S, 6.89.

2-{[1-Phenyl-3-(4-bromophenyl)pyrazol-4-yl]methylenehydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid (6f)

Yield 71%; off-white powder; mp 200–202°C; ¹³C NMR: δ 38.4, 44.8, 106.1, 177.5, 177.9, 163.7, 118.9 (2C), 123.9 (1C), 132.4 (2C), 126.4, 128.9, 129.7 (2c), 131.4, 134.3, 138.8, 148.9, 163.2, 171.7 and 175.4; MS (ESI) m/z 465 (M+H)⁺. Anal. Calcd for C₂₁H₁₆BrN₅O₃S: C, 50.61; H, 3.24; N, 14.05; S, 6.43. Found: C, 50.63; H, 3.19; N, 14.04; S, 6.39.

Acknowledgments

The authors are thankful to Professor D. B. Ingle for discussion and guidance. The authors thank SAIF, Central Drug Research Institute (CDRI), Lucknow for spectral analysis.

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Received: 2017-6-25

Accepted: 2017-11-6

Published Online: 2018-3-21

Published in Print: 2018-4-25

This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Articles in the same Issue

https://doi.org/10.1515/hc-2017-0130

Keywords for this article

baker’s yeast; 2-hydrazono-4-thiazolidinon-5-yl-acetic acids; one-pot multicomponent reaction; ultrasonication

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