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Synthesis and Antimicrobial Activity of Oxazolone, Imidazolone and Triazine Derivatives Containing Benzothiophene

  • Naganagowda, Gadada (Research Center for Bioorganic Chemistry (RCBC), Department of Chemistry, Faculty of Science, Chulalongkorn University) ;
  • Petsom, Amorn (Research Center for Bioorganic Chemistry (RCBC), Department of Chemistry, Faculty of Science, Chulalongkorn University)
  • Received : 2011.04.12
  • Accepted : 2011.09.01
  • Published : 2011.11.20

Abstract

3-Chloro-1-benzothiophene-2-carbonyl chloride 1 was reacted with glycine in acetone to give 3-chloro-1-benzothiophen-2-yl-carbonylaminoacetic acid 2. Various aldehydes on treatment with compound 2 in acetic anhydride to gave 1,3-oxazol-5-ones 3a-d. These oxazolones was treated with aromatic amines or hydrazides to get various imidazol-4-ones 4a-t or 5a-l. Oxazolones 3a-d was also treated with aromatic hydrazines, expansion of five member oxazole ring to six member triazine ring occurs to yield 1,2,4-triazin-6-ones 6a-h. The structures of all the synthesized compounds were confirmed by spectral data and had been screened for antibacterial activity.

Keywords

References

  1. Garcia-Valverde, M.; Tomas, T. Molecules 2005, 10, 318-320. https://doi.org/10.3390/10020318
  2. Boger, D. L. Chem. Rev. 1986, 86, 781-793. https://doi.org/10.1021/cr00075a004
  3. Monge, A.; Palop, J.; Ramirez, C.; Font, M.; Fernandez-Alvarez, E. Eur. J. Med. Chem. 1991, 26, 179-188. https://doi.org/10.1016/0223-5234(91)90027-K
  4. Labouta, I. M.; Eshba, N. H.; Salama, H. M. Farm. Sci. Ed. 1998, 16, 29-38.
  5. AbdEl-Samii, Z. K. J. Chem. Tech. Biotech. 1992, 53, 143-146.
  6. Leach, M. J.; Nobls, M. S. Eur. Pat. Appl-EP459, 829; Chem. Abstr. 1992, 116, 128970x.
  7. Maillard, J.; Vincent, M.; Morin, R.; Benard, M. Chem. Abstr. 1962, 57, 1525-1528.
  8. Najer, H.; Giudicelli, R.; Moral, C.; Menin, M. Bull. Soc. Chem. France. 1966, 153, 40-44.
  9. Kennedy, D. A.; Summers, L. A. J. Heterocycl. Chem. 1981, 409, 39-41.
  10. Yale, H. I.; Losee, K. J. Med. Chem. 1966, 9, 478-480. https://doi.org/10.1021/jm00322a007
  11. Piala, J. J.; Yale, H. L. Chem. Abstr. 1964, 61, 8317-8319.
  12. Capan, G.; Ulusoy, N.; Ergenc, N.; Kiraz, M. Monatsh. Chem. 1999, 130, 1399-1401.
  13. Vigorita, M. G.; Ottana, R.; Monforte, F.; Maccari, R.; Trovato, A.; Monforte, M. T.; Taviano, M. F. Bioorg. Med. Chem. Lett. 2001, 11, 2791-2793. https://doi.org/10.1016/S0960-894X(01)00476-0
  14. Kavitha, C. V.; Basappa, S.; Nanjunda, S.; Mantelingu, K.; Doreswamy, S.; Sridhar, M. A.; Prasad, J. S.; Rangappa, K. S. Bioorg. Med. Chem. 2006, 14, 2290-2293. https://doi.org/10.1016/j.bmc.2005.11.017
  15. Ottana, R.; Maccari, R.; Barreca, M. L.; Bruno, G.; Rotondo, A.; Rossi, A.; Chiricosta, G.; Paola, R.; Sautebin, L.; Cuzzocrea, S.; Vigorita, M. G. Bioorg. Med. Chem. 2005, 13, 4243-4226. https://doi.org/10.1016/j.bmc.2005.04.058
  16. Kucukguzel, G.; Kocatepe, A.; De Clercq, E.; Sahin, F.; Gulluce, M. Eur. J. Med. Chem. 2006, 41, 353-355. https://doi.org/10.1016/j.ejmech.2005.11.005
  17. Parkey, S.; Castle, N. J. Heterocycl. Chem. 1986, 23, 1571-1577. https://doi.org/10.1002/jhet.5570230563
  18. British Pharmacopoeia. 2005, Vol. IV, p. A300 Appendix XIV.
  19. Vincent, J. G.; Vincent, H. W. Proc. Soc. Exp. Biol. Med. 1944, 55, 162-165. https://doi.org/10.3181/00379727-55-14502

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