Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Tetrazolo[1,5-a]quinoxaline based Azetidinones ＆ Thiazolidinones as Potent Antibacterial ＆ Antifungal Agents

  • Kumar, Shiv (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University)) ;
  • Khan, S.A. (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University)) ;
  • Alam, Ozair (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University)) ;
  • Azim, Rizwan (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University)) ;
  • Khurana, Atul (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University)) ;
  • Shaquiquzzaman, M. (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University)) ;
  • Siddiqui, Nadeem (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University)) ;
  • Ahsan, Waquar (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University))
  • Received : 2010.12.20
  • Accepted : 2011.05.19
  • Published : 2011.07.20
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Abstract

4-Chlorotetrazolo[1,5-a]quinoxaline (III) was synthesized by azide (2+3) cycloaddition of 2,3-dichloroquinoxaline (II). Compound (III) on further refluxing with hydrazine hydrate furnished 4-hydrazinotetrazolo[1,5-a]quinoxaline (IV). Further refluxing of (IV) with different aromatic aldehydes in methanol yielded corresponding Schiff's bases V(a-j). Various 4-aminotetrazolo[1,5-a]quinoxaline based azetidinones VII(a-j) were synthesized by stirring the compounds V(a-j), at low temperature, with equimolar mixture of chloroacetylchloride & triethylamine in dry benzene, while 4-aminotetrazolo[1,5-a]quinoxaline based thiazolidinones VIII(a-j) were synthesized by refluxing Schiff's bases V(a-j) with thioglycolic acid in oil-bath. The structures of all the compounds were confirmed on the basis of $^1H$-NMR & FT-IR spectral data. All the newly synthesized compounds were screened for in-vitro antimicrobial activity against E. coli, S. aureus, K. pneumoniae & P. aeruginosa & antifungal activity against C. albicans. Few of them have exhibited the promising activity.

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References

  1. Grande, F.; Aiello, F.; Grazia, O. D.; Brizz,i A.; Garofalo, A.; Neamati, N. Bioorg. Med. Chem. 2007, 15, 288. https://doi.org/10.1016/j.bmc.2006.09.073
  2. Amin, K. M.; Ismail, M. M. F.; Noaman, E.; Soliman, D. H.; Ammar, Y. A. Bioorg. Med. Chem. 2006, 14, 6917. https://doi.org/10.1016/j.bmc.2006.06.038
  3. Zarranz, B.; Jaso, A.; Aldana, I.; Monge, A. Bioorg. Med. Chem. 2004, 12, 3711. https://doi.org/10.1016/j.bmc.2004.04.013
  4. Lee, H.; Cho, S.; Namgoong, K.; Jung, J. K.; Yang, S. Bioorg. Med. Chem. Lett. 2004, 14, 1235. https://doi.org/10.1016/j.bmcl.2003.12.046
  5. Diana, P.; Martorana, A.; Barraja, P.; Montalbaro, A. J. Med. Chem. 2008, 51, 2387. https://doi.org/10.1021/jm070834t
  6. Chung, H. J.; Jung, O. J.; Chae, M. J.; Hong, S. Y.; Chung, K. H.; Lee, S. K. Bioorg. Med. Chem. Lett. 2005, 15, 3380. https://doi.org/10.1016/j.bmcl.2005.05.022
  7. Katsuyuki, A.; Obata, T.; Yamazaki, Y.; Mori, Y.; Hirokawa, H.; Koseki, J.; Hattori, T.; Niitsu, K.; Takeda, S.; Aburada, M.; Miyamoto, K. Chem. Pharm. Bulletin 2007, 55, 255. https://doi.org/10.1248/cpb.55.255
  8. Carta, A.; Loriga, M.; Paglietti, G.; Mattana, A.; Fiori, P. L.; Mollicotti, P.; Sechi, L.; Zanetti, S. Eur. J. Med. Chem. 2004, 39, 195. https://doi.org/10.1016/j.ejmech.2003.11.008
  9. Carta, A.; Paglietti, G.; Nikookar, M. E. R.; Sanna, P.; Sechi, L.; Zanetti, S. Eur. J. Med. Chem. 2002, 37, 355. https://doi.org/10.1016/S0223-5234(02)01346-6
  10. Tandon, V. K.; Yadav, D. B.; Maurya, H. K.; Chaturvedi, A. K.; Shukla, P. K. Bioorg. Med. Chem. 2006, 14, 6120. https://doi.org/10.1016/j.bmc.2006.04.029
  11. Kotharkar, S. A.; Shinde, D. B. Bioorg. Med. Chem. Lett. 2006, 16, 6181. https://doi.org/10.1016/j.bmcl.2006.09.040
  12. Mashevskaya, I. V.; Makhmudov, R. R.; Aleksandrova, G. A.; Golovnira, O. V.; Duvalov, A. V.; Maslivets, A. N. Pharm. Chem. J. 2001, 35, 196. https://doi.org/10.1023/A:1010475811489
  13. Mashevskaya, I. V.; Tolmacheva, I. A.; Voronova, E. V.; Odegova, T. F.; Alkeksandrova, G. A.; Goleneva, A. F.; Kot'tsova, S. V.; Maslivets, A. N. Pharm. Chem. J. 2002, 36, 86.
  14. Vyas, D. A.; Chauhan, N. A.; Parikh, A. R. Indian J. Chem. 2007, 46B, 1699.
  15. Jaso, A.; Zarranz, B.; Aldana, I.; Monge, A. Eur. J. Med. Chem. 2003, 38, 791. https://doi.org/10.1016/S0223-5234(03)00137-5
  16. Zarranz, B.; Jaso, A.; Aldana, I.; Monge, A. Bioorg. Med. Chem. 2003, 11, 2149. https://doi.org/10.1016/S0968-0896(03)00119-6
  17. Jaso, A.; Zarranz, B.; Aldana, I.; Monge, A. J. Med. Chem. 2005, 48, 2019. https://doi.org/10.1021/jm049952w
  18. Seitz, L. E.; Suling, W. J.; Reynolds, R. C. J. Med. Chem. 2002, 45, 5604. https://doi.org/10.1021/jm020310n
  19. Burguete, A.; Pontiki, E.; Litina, D. H.; Villar, R.; Vicente, E.; Solano, B.; Ancizu, S.; Aldana, I.; Monge, A. Bioorg. Med. Chem. Lett. 2007, 17, 6439. https://doi.org/10.1016/j.bmcl.2007.10.002
  20. Wagle, S.; Adhikari, A. V.; Kumari, N. S. Indian J. Chem. 2008, 47B, 439.

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