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Abstract
The 4-thiazolidinone ring system is a fundamental structure which is present in a large variety of synthetic pharmaceuticals that has a wide range of potential biological effects. In this work, thioglycolic acid and 6-chloro-N-(substituted benzylidene)benzothiazol-2-amine were condensed in DMF solvent in the presence of ZnCl2 to obtain novel 3- (6-chlorobenzo[d]thiazol-2-yl)-2-(substituted aryl)thiazolidin-4-one derivatives. The structure of the synthesized compounds (3a-j) were confirmed using IR, 1H & 13C NMR and mass spectroscopy.
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References
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References
J.V. Popli, M.R. Kumbhare, A.R. Surana, M.R. Bhalerao and P.A. Agrawal, Benzothiazole Analogues and their Biological Aspects: A Review, Indian J. Chem., 60B, 1659 (2021).
A.A. Geronikaki, A.A. Lagunin, D.I. Hadjipavlou-Litina, P.T. Eleftheriou, D.A. Filimonov, V.V. Poroikov, I. Alam and A.K. Saxena, Computer-Aided Discovery of Anti-Inflammatory Thiazolidinones with Dual Cyclooxygenase/Lipoxygenase Inhibition, J. Med. Chem., 51, 1601 (2008); https://doi.org/10.1021/jm701496h
A.A. Bekhit, H.T.Y. Fahmy, S.A.F. Rostom and A. Bekhit, Synthesis and Biological Evaluation of Some Thiazolylpyrazole Derivatives as Dual Anti-inflammatory Antimicrobial Agents, Eur. J. Med. Chem., 45, 6027 (2010); https://doi.org/10.1016/j.ejmech.2010.10.001
S.K. Bhati and A. Kumar, Synthesis of New Substituted Azetidinoyl and Thiazolidinoyl-1,3,4-thiadiazino[6,5-b]indoles as Promising Antiinflammatory Agents, Eur. J. Med. Chem., 43, 2323 (2008); https://doi.org/10.1016/j.ejmech.2007.10.012
M.V. Diurno, O. Mazzoni, E. Piscopo, A. Calignano, F. Giordano and A. Bolognese, Synthesis and Antihistaminic Activity of Some Thiazolidin4-ones, J. Med. Chem., 35, 2910 (1992); https://doi.org/10.1021/jm00093a025
A. Rao, A. Chimirri, S. Ferro, A.M. Monforte, P. Monforte and M. Zappala, Microwave-Induced Synthesis of Benzimidazole and Thiazolidinone Derivatives as HIV-1 RT Inhibitors (VT-1030LP), ARKIVOC, 5, 147 (2004); https://doi.org/10.3998/ark.5550190.0005.514
K. Danylo, K. Dmytro, V. Olexandr, Z. Lucjusz and L. Roman, A Facile Synthesis and Anticancer Activity Evaluation of Spiro[thiazolidinoneisatin] conjugates, Sci. Pharm., 79, 763777 (2011).
A. Gursoy and N. Terzioglu, Synthesis and Isolation of New Regioisomeric 4-Thiazolidinones and their Anticonvulsant Activity, Turk. J. Chem., 29, 247 (2005).
N. Siddiqui, M.F. Arshad, S.A. Khan and W. Ahsan, Sulfonamide Derivatives of Thiazolidin-4-ones with Anticonvulsant Activity against Two Seizure Models: Synthesis and Pharmacological Evaluation, J. Enzyme Inhib. Med. Chem., 25, 485 (2010); https://doi.org/10.3109/14756360903282833
K.C. Asati, S.K. Srivastava and S.D. Srivastava, Synthesis of 5-Arylidene2-aryl-3-(benzotriazoloacetamidyl)-1,3-thiazolidin-4-ones as Analegesic and Antimicrobial Agents, Indian J. Chem., 45B, 526 (2006).
R.P. Gore, Microwave Assisted Synthesis, Characterization of Azole Thiazolidinoneacetamides, J. Pharm. Res., 8, 1624 (2014).
N.B. Patel and F.M. Shaikh, New 4-Thiazolidinones of Nicotinic Acid with 2-Amino-6-methylbenzothiazole and their Biological Activity, Sci. Pharm., 78, 753 (2010); https://doi.org/10.3797/scipharm.1009-15
S.R. Pattan, C.H. Suresh, V.D. Pujar, V.V.K. Reddy, V.P. Rasal and B.C. Koti, Synthesis and Antidiabetic Activity of 2-Amino-[5′(4-Sulphonylbenzylidine)-2,4-thiazolidinedione]-7-chloro-6-fluoro benzothiazole, Indian J. Chem., 44B, 2404 (2005).
N.B. Patel and F.M. Shaikh, Synthesis and Antimicrobial Activity of New 4-Thiazolidinone Derivatives Containing 2-Amino-6-methoxybenzothiazole, Saudi Pharm. J., 18, 129 (2010); https://doi.org/10.1016/j.jsps.2010.05.002
D. Havrylyuk, L. Mosula, B. Zimenkovsky, O. Vasylenko, A. Gzella and R. Lesyk, Synthesis and Anticancer Activity Evaluation of 4-Thiazolidinones Containing Benzothiazole Moiety, Eur. J. Med. Chem., 45, 5012 (2010); https://doi.org/10.1016/j.ejmech.2010.08.008
V. Patil, K. Tilekar, S. Mehendale-Munj, R. Mohan and C.S. Ramaa, Synthesis and Primary Cytotoxicity Evaluation of New 5-benzylidene2,4-thiazolidinedione Derivatives, Eur. J. Med. Chem., 45, 4539 (2010); https://doi.org/10.1016/j.ejmech.2010.07.014
G. Viscardi, P. Savarino, E. Barni and R. Carpignano, Heterocyclic Xazolopyridine intermediates, J. Heterocycl. Chem., 27, 1825 (1990); https://doi.org/10.1002/jhet.5570270657
R.P. Sonawane and A.R. Baraskar, Synthesis and Characterization of 6-Chloro-N-(substituted benzylidene)benzothiazol-2-amine by Microwave Irradiation, Heterocycles, 104, 2219 (2022); https://doi.org/10.3987/COM-22-14754
S.B. Desai, P.B. Desai and K.R. Desai, Synthesis of Some Schiff Bases, Thiazolidinones and Azetidinones Derived from 2,6-Diaminobenzo- [1,2-d:4,5-d]isthiazole and their Anticancer Activities, Heterocycl. Commun., 7, 83 (2001); https://doi.org/10.1515/HC.2001.7.1.83
A.N. Ayyash and A.O. Hammady, Synthesis and Bioactivity Screening of New 1, 3-Thiazolidin-4-One Compounds Bearing (Thiadiazols / Triazoles) Moieties, J. Phys. Conf. Ser., 1660, 012025 (2020); https://doi.org/10.1088/1742-6596/1660/1/012025