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004-AJOMC 30726 (35-38)

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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.

Keywords

Benzothiazole 4-Thiazolidinone Thioglycolic acid Schiff bases, Biological activities

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Baraskar, A. R., Sonawane, R., Kshirsagar, Y., & Pathan, S. (2024). Synthesis and Characterization of 4-Thiazolidinones Derivatives with 6-Chlorobenzothiazole Moiety. Asian Journal of Organic & Medicinal Chemistry, 8(3), 35–38. https://doi.org/10.14233/ajomc.2023.AJOMC-P30726
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References

  1. 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).
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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).
  8. A. Gursoy and N. Terzioglu, Synthesis and Isolation of New Regioisomeric 4-Thiazolidinones and their Anticonvulsant Activity, Turk. J. Chem., 29, 247 (2005).
  9. 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
  10. 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).
  11. R.P. Gore, Microwave Assisted Synthesis, Characterization of Azole Thiazolidinoneacetamides, J. Pharm. Res., 8, 1624 (2014).
  12. 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
  13. 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).
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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

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