Efficient Synthesis and Antimicrobial Activity of 2-Pyridyl-4-thiazolidinones from 2-Chloro Nicotinaldehydes

Document Type : Research Note

Authors

1 Crop Protection Chemicals Division, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad-500 007, Telangana, INDIA

2 Biology Division, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad-500 007, Telangana, INDIA

Abstract

Several new 2-pyridyl-4-thiazolidinones are synthesized in an efficient manner evading using any catalyst or base. Simple workup procedure, good yields, and mild reaction conditions are the salient features of this method. All the synthesized compounds are screened
for antimicrobial activity against several organisms.

Keywords

Main Subjects


[1] Roth H.J., Kleemann A., “Pharmaceutical Chemistry. Drug Synthesis Eds. Prentice Hall Europe, London, 1: 407-  (1998).
[2] Bakhite E.A., Abdel-Rahman A.E., Mohamed O.S., Thabet E.A., Synthesis and Reactions of some New Heterocyclic Compounds Containing the Thienyl Thieno[2,3-b]pyridine Moiety, Phosphorus Sulfur Silicon and the Related Elements, 179: 1983-2006 (2004).
[3] Singh S.P., Parmar S.S., Raman K., Stenberg V., Chemistry and Biological Activity of Thiazolidinones, Chem. Rev., 81: 175-203 (1981).
[4] Trost B.M. ed., “Comprehensive Organic Synthesis”, Pergamon Press, Oxford 2: 133 (1991).
[5] Kucukguzel G., Kocatepe A., De Clercq E., Sahin, F., Gulluce M., Synthesis and Biological Activity of
4-Thiazolidinones, Thiosemicarbazides Derived from Diflunisal Hydrazide,
Eur. J. Med. Chem., 41: 353-359 (2006).
[6] Tenorio R.P., Carvalho C.S., Pessanha C.S., de Lima J.G., de Faria A.R., Alves A.J., de Melo E.J.T.,
Goes A.J.S., Synthesis of Thiosemicarbazone and 4-Thiazolidinone Derivatives and Their in Vitro anti-Toxoplasma gondii Activity, Bioorg. Med. Chem. Lett., 15: 2575-2578 (2005).
[8] Eid A.I., Ragab F.A., EI-Ansary S.L., EI-Gazayerly S.M., Mourad F.E., Synthesis of New 7-Substituted 4-Methylcoumarin Derivatives of Antimicrobial Activity, Arch. Pharm. 327: 211-213 (1994).
[10] Capan G., Ulusoy N., Ergenc N., Kiraz M., New 6-Phenylimidazo[2,1-b]thiazole Derivatives: Synthesis and Antifungal Activity, Montasch Chem., 130: 1399-1407 (1999).
[13] Gududuru V., Hurh E., Dalton J.T., Miller D.D., Discovery of 2-arylthiazolidine-4-carboxylic Acid Amides as a New Class of Cytotoxic Agents for Prostate Cancer, J. Med. Chem., 48: 2584-2588 (2005).
[14] Havrylyuk D., Mosula L., Zimenkovsky B., Vasylenko O., Gzella A., Lesyk R., Synthesis and Anticancer Activity Evaluation of 4-thiazolidinones Containing Benzothiazole Moiety, Eur. J. Med. Chem., 45: 5012-5021 (2010).
[17] Babaoglu K., Page M.A., Jones V.C., McNeil M.R., Dong C., Naismith J.H., Lee R.E., Novel Inhibitors of an Emerging Target in Mycobacterium Tuberculosis; Substituted Thiazolidinones as Inhibitors of dTDP-Rhamnose Synthesis, Bioorg. Med. Chem. Lett., 13: 3227-3230 (2003).
[18] Andres C.J., Bronson J.J., D’Andrea S.V., Deshpande M.S., Falk P.J., Grant-Young K.A., Harte W.E., Ho H.–T., Misco P.F., Robertson J.G., Stock D., Sun Y., Walsh A.W., 4-Thiazolidinones: Novel Inhibitors of the Bacterial Enzyme MurB, Bioorg. Med. Chem. Lett., 10: 715-717 (2000).
[19] Mahran M.A., EI-Nassry S.M.F., Allam S.R., Elzawawy L.A., Synthesis of Some New Benzothiazole Derivatives as Potential Antimicrobial and Antiparasitic Agents, Die Pharmazie 58: 527-530 (2003).
[20] Hu J., Wang Y., Wei X., Wu X., Chen G., Cao G., Shen X., Zhang X., Tang Q., Liang G., Li X., Synthesis and Biological Evaluation of Novel Thiazolidinone Derivatives as Potential Anti-Inflammatory Agents, Eur. J. Med. Chem., 64: 292-301 (2013).
[21] Schenone S., Bruno O., Ranise A., Bondavalli F., Filippelli W., Falcone G., Giordano L., Vitelli M.R., 3-Arylsulphonyl-5-arylamino-1,3,4-thiadiazol-2(3H)ones as Anti-Inflammatory and Analgesic Agents, Bioorg. Med. Chem., 9: 2149-2153 (2001).
[22] Barreca M.L., Chimirri A., Luca L.D., Monforte A.–M., Monforte P., Rao A., Zappala M., Balzarini J.,
De Clercq E., Pannecouque C., Witvrouw, M., Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as Potent Anti-HIV-1 Agents, Bioorg. Med. Chem. Lett.,11: 1793-1796 (2001).
[23] Suzuki M., Morita K., Yukioka H., Miki N., Mizutani A., Synthesis and Herbicidal Activity of
4-Thiazolone Derivatives and Their Effect on Plant Secretory Pathway,
J. Pesti. Sci., 28: 37-43 (2003).
[24] Rawal R.K., Prabhakar Y.S., Katti S.B., De Clercq E., 2-(Aryl)-3-furan-2-ylmethyl-thiazolidin-4-ones as Selective HIV-RT Inhibitors, Bioorg. Med. Chem., 13: 6771-6776 (2005).
[25] Dayam R., Sanchez T., Clement O., Shoemaker R., Sei S., Neamati N., β-Diketo Acid Pharmacophore Hypothesis. 1. Discovery of a Novel Class of HIV-1 Integrase Inhibitors, J. Med. Chem., 48: 111-120 (2005).
[26] Diurno M.V., Mazzoni O., Piscopo E. Calignano A., Giordano F., Bolognese A., Synthesis and Antihistaminic Activity of Some Thiazolidin-4-ones,  J. Med. Chem., 35: 2910-2912 (1992).
[27] Reddy K.A., Lohray B.B., Bhushan V., Bajji A.C., Reddy K.V., Reddy P.R., Hari Krishna T., Rao I.N., Jajoo H.K., Mamidi Rao N.V.S., Chakrabarti R., Kumar T.D., Rajagopalan R., Novel Antidiabetic and Hypolipidemic Agents. 3. Benzofuran-Containing Thiazolidinediones, J. Med. Chem., 42: 1927-1940 (1999).
[28] Bolognese A.,Correale G.,Manfra M.,Lavecchia A., Novellino E., Barone V., Thiazolidin-4-one Formation. Mechanistic and Synthetic Aspects of the Reaction of Imines and Mercaptoacetic Acid under Microwave and Conventional Heating, Org. Biomol. Chem., 2: 2809-2813 (2004).
[29] Cunico W., Gomes C.R.B., Ferreira M.L.G., Capri L.R., Soares M., Wardell S.M.S.V., One-Pot Synthesis of 2-isopropyl-3-benzyl-1,3-thiazolidin-4-ones and 2-phenyl-3-isobutyl-1,3-thiazolidin-4-ones From Valine, Arenealdehydes and Mercaptoacetic Acid, Tetrahedron Lett., 48:6217-6220 (2007).
[30] Srivastava T., Haq W., Katti S.B.,Carbodiimide Mediated Synthesis of 4-Thiazolidinones by One-Pot Three-Component Condensation, Tetrahedron, 58: 7619-7624 (2002).
[31] Srivastava S.K., Srivastava S.L., Srivastava S.D., Synthesis of 5-aryl-2-3-(2-chlorophenothiazinoacetamidyl)-1,3-thiazolidin-4-Ones as Antifungal and Anticonvulsant, J. Ind. Chem. Soc., 77:104-105 (2000).
[32] Sharma R.C., Kumar D., Synthesis of some New Thiazolidin-4-Ones as Possible Antimicrobial Agents, J. Ind. Chem. Soc., 77: 492-493 (2002).
[33] Gududuru V., Nguyen V., Dalton J.T., Miller D.D., Efficient Microwave Enhanced Synthesis of
4-Thiazolidinones,
Synlett, 13: 2357-2358 (2004).
[34] Zhou Z.-Z., Huang W., Ji F.-Q., Ding M.-W., Yang G.-F., Construction of a Combinatorial Library of
2-(4-oxo-4H-1-benzopyran-3-yl)-4-thiazolidinones by Microwave –Assisted One-Pot Parallel Syntheses,
Heteroatom Chem., 18: 381-389 (2007).
[35] Holmes C.P., 1996 WO 96/ 00148.
[36] Stephanie E., Justus A., Hodges J.C., Wilson M.W., Generation of a Library of 4-thiazolidinones Utilizing Polymer Supported Quench (PSQ) Reagent Methodology, Biotech. Bioeng., 61: 17-22 (2000).
[37] Kumar Ch.N.S.S.P., Srihari E., Ravinder M., Kumar K.P., Murthy U.S.N., Jayathirtha Rao V., DBU Promoted Facile Synthesis of New Thieno[2,3-b]Pyridine/ Quinoline Derivatives and Their Antimicrobial Evaluation,  J. Het. Chem., 50: E131-E135 (2013).
[38] Reddy N.T., Ravinder M., Bagul P., Ravikanti K., Bagul C., Nanubolu J.B., Srinivas K., Banarjee S.K., Jayathirtha Rao V., Synthesis and Biological Evaluation of New Epalrestat Analogues as Aldose Reductase Inhibitors (ARIs), Eur. J. Med. Chem., 71: 53-66 (2014).
[39] Gangadasu B., Narender P., Bharath Kumar S., Ravinder M., Ananda Rao B., Ramesh Ch., China Raju B., Jayathirtha Rao V., Facile and Selective Synthesis of Chloronicotinaldehydes by the Vilsmeier Reaction, Tetrahedron, 62: 8398-8403 (2006).
[40] Amaresh R.R., Perumal P.T., A Novel Route to the Synthesis of 3-Pyridine Carboxaldehydes by Vilsmeier Reagent, Syn. Commun., 30(13): 2269-2274 (2000).
[41] NCCL-National Committee for Clinical Laboratory Standards (NCCLS). Standard Methods for Dilution Antimicrobial susceptibility tests for Bacteria Which Grow Aerobically. Nat. Comm., Clin Lab Stands Villanova, (1982).