Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Solvent Free Microwave Accelerated Synthesis of Heterocyclic Thiazolidin-4-ones as Antimicrobial and Antifungal Agents

  • Received : 2010.01.04
  • Accepted : 2010.03.03
  • Published : 2010.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

A simple and efficient method has been developed for conversion of arenecarbaldehyde-3-methylquinoxalin-2-ylhydrazones to 3-(2-methylquinoxalin-3-yl)-2-(substitutedphenyl)thiazolidin-4-ones in good yields using microwave irradiation technique on silica as solid support under solvent free conditions. The synthesized compounds were characterized by elemental microanalysis, infrared spectroscopy, $^1H$ NMR, and mass spectroscopy. All the synthesized thiazolidinones were investigated for their antimicrobial and antifungal activities. The results of the biological activities revealed that the compounds 3b, 3d, 3f and 3h exhibited excellent antibacterial activities while 3d and 3h exhibited good antifungal activity.

Keywords

References

  1. Kurasawa, Y.; Takad, A. Heterocycles 1986, 24, 2321. https://doi.org/10.3987/R-1986-08-2321
  2. Kurasawa, Y.; Muramatsu, M.; Yamazaki, K.; Tajima, S.; Okamoto, Y.; Takada, A. J. Heterocycl. Chem. 1986, 23, 1379. https://doi.org/10.1002/jhet.5570230524
  3. Skata, G.; Makino, K.; Kurasawa, Y. Heterocycles 1988, 27, 2481. https://doi.org/10.3987/REV-88-397
  4. Metzner, J.; Lippmann, E.; Weber, F .G.; Westphal, G. Pharmazie 1981, 36, 368.
  5. Shinde, B. R.; Pai, N. R. Indian Drugs 1989, 27, 32.
  6. Boido, A.; Vazzana, I.; Sparatore, F. I L Farmaco 1994, 49, 97.
  7. Love, B.; Musser, J. H.; Brown, R. E.; Jones, H.; Kahen, R.; Huang, F. C.; Khandwala, A.; Sonnino, G. P.; Leibowitz, M. J. Med. Chem. 1985, 28, 363. https://doi.org/10.1021/jm00381a016
  8. Rao, V. S.; Chandra Sekhar, K. V. G. Synth. Comm. 2004, 34, 2153. https://doi.org/10.1081/SCC-120038493
  9. Kumar, D.; Chandra Sekhar, K. V. G.; Dhillon, H.; Rao, V. S.; Varma, R. S. Green Chem. 2004, 6, 156. https://doi.org/10.1039/b315031c
  10. Chandra Sekhar, K. V. G.; Rao, V. S.; Murali Krishna Kumar, M. J. Enzym. Inhib. Med. Ch. 2009, 24, 871. https://doi.org/10.1080/14756360802447750
  11. Banik, B. K.; Manhas, M. S.; Newas, S. N. ; Bose, A. K. Bioorg. Med. Chem. Lett. 1993, 33, 2363.
  12. Varma, R. S. Green Chem. 1999, 1, 43. https://doi.org/10.1039/a808223e
  13. Bolognese, A.; Correale, G.; Manfra, M.; Lavecchia, A.; Novellino, E.; Barone, V. Org. Biomol. Chem. 2004, 2, 2809. https://doi.org/10.1039/b405400h
  14. Sattigeri, V. J.; Soni, A.; Singhal, S.; Khan, S.; Pandya, M.; Bhateja, P.; Mathur, T.; Rattan, A.; Khanna, J.; Mehta, A. Arkovic 2005, ii, 46.
  15. Cacic, M.; Molnar, M.; Balic, T.; Rajkovic, V. Molecules 2009, 14, 2501. https://doi.org/10.3390/molecules14072501
  16. Singh, S. P.; Parmar, S. S.; Raman, K.; Stenberg, V. I. Chem. Rev. 1981, 81, 175. https://doi.org/10.1021/cr00042a003
  17. Hamama, W. S.; Ismail, M. A.; Shaaban, S.; Zoorob, H. H. J. Heterocyclic Chem. 2008, 45, 939. https://doi.org/10.1002/jhet.5570450401
  18. Garnaik, B. K.; Behera, R. K. Indian J. Chem. 1988, 27B, 1157.
  19. Vladzimirskaya, V.; Novikevich, T.; Demchuk, G. Farm. Zh. (Kiev) 1991, 6, 67.
  20. Lakhan, R.; Singh, R. L. J. Agric. Food Chem. 1991, 39, 580. https://doi.org/10.1021/jf00003a029
  21. Pawar, R. P.; Andurkar, M.; Vibhute, Y. B. J. Indian Chem. Soc. 1999, 76, 271.
  22. El-Feky, S. A. H. Pharmazie 1993, 48, 894.
  23. Grasso, S.; Chimirri, A.; Zappala, M. Farmaco 1986, 41, 713.
  24. Samir, B.; Wesam, K.; Ahmed, A. F. Eur. J. Med. Chem. 2007, 42, 948. https://doi.org/10.1016/j.ejmech.2006.12.025
  25. Baihua. US Pat 6821991, 2004.
  26. Shiho, D.; Tagami, S. J. Am. Chem. Soc. 1960, 82, 4044. https://doi.org/10.1021/ja01500a058
  27. Barry, A. L. The Antimicrobial Susceptibility Test, Principle and Practices, 4th ed.; ELBS: London, 1999; p 180.
  28. Seelay, H. W.; Denmark, P. J. V. Microbes in action; W. H. Freeman & Co: New York, 1972.
  29. Vyas, D. A.; Chauhan, N. A.; Parikh, A. R. Indian J. Chem. 2007, 46B, 1699.
  30. Prakash, O.; Bhardwaj, V.; Kumar, R.; Tyagi, P.; Aneja, K. R. Eur. J. Med. Chem. 2004, 39, 1073. https://doi.org/10.1016/j.ejmech.2004.06.011

Cited by

  1. Microwave-assisted synthesis of five-membered S-heterocycles vol.11, pp.2, 2014, https://doi.org/10.1007/s13738-013-0325-2
  2. Microwave-Mediated InCl3-Catalyzed Three-Component Annelation of Thiadiazinе Ring onto 4-Amino-4H-[1,2,4]Triazole-3-Thiol vol.50, pp.4, 2014, https://doi.org/10.1007/s10593-014-1509-0
  3. ChemInform Abstract: Solvent‐Free Microwave Accelerated Synthesis of Heterocyclic Thiazolidin‐4‐ones as Antimicrobial and Antifungal Agents. vol.41, pp.40, 2010, https://doi.org/10.1002/chin.201040175
  4. Synthesis of Triazoloquinoxalines as Antitubercular Agents vol.32, pp.8, 2011, https://doi.org/10.5012/bkcs.2011.32.8.2657
  5. Synthesis of thiazolidinimines/thiazinan-2-imines via three-component coupling of amines, vic-dihalides and isothiocyanates under metal-free conditions vol.51, pp.9, 2021, https://doi.org/10.1080/00397911.2021.1880594