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Vol. 27 No. 10 (2015): Vol 27 Issue 10

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Synthesis and Antibacterial Studies of Some Alkynylated Benzo[a]phenoxazin-5-one and 1,4-Naphthoquinone Derivatives

https://doi.org/10.14233/ajchem.2015.19012
M.A. Ezeokonkwo
Department of Pure & Industrial Chemistry, University of Nigeria, Nsukka, Enugu State, Nigeria
F.O. Ugwuona
Department of Pure & Industrial Chemistry, University of Nigeria, Nsukka, Enugu State, Nigeria
I.C. Ugwu
Department of Veterinary Pathology and Microbiology, University of Nigeria, Nsukka, Nigeria

Corresponding Author(s) : M.A. Ezeokonkwo

mercy.ezeokonkwo@unn.edu.ng; mercy.ezeokonkwo@yahoo.com

Asian Journal of Chemistry, Vol. 27 No. 10 (2015): Vol 27 Issue 10

Abstract

Various 6-alkynyl-5H-benzo[a]phenoxazin-5-ones (5a-e) and 2-chloro-3-alkynyl-1,4-naphthoquinones (6a-e) were synthesized using modified Sonogashira protocol. The chemical structures of the synthesized compounds were established by spectroscopic data. In vitro antibacterial screening of these compounds was carried out on multi-resistant bacterial strains using gentamycin and ampicillin as a reference standard. The bacteria strains used were Gram-positive bacterium (Staphylococcus aureus) and Gram-negative bacteria (Pseudomonas aeruginosa, Escherichia coli I, Escherichia coli 12 and Klebsiella pneumonia). All the tested compounds showed moderate to excellent activity against one or more tested micro-organisms. Compounds 6d (MIC 0.30 mg/mL) and 6b (MIC 1.05 mg/mL) showed highest activity against Gram-negative (Klebsiella pneumoniae) and Gram-positive (Staphylococcus aureus) respectively.

Keywords

Sonogashira cross-coupling reaction Benzo[a]phenoxazin-5-ones 1 4-Naphthoquinones Terminal alkynes
Ezeokonkwo, M., Ugwuona, F., & Ugwu, I. (2015). Synthesis and Antibacterial Studies of Some Alkynylated Benzo[a]phenoxazin-5-one and 1,4-Naphthoquinone Derivatives. Asian Journal of Chemistry, 27(10), 3843–3850. https://doi.org/10.14233/ajchem.2015.19012
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References
  1. Z. Xu and E. Negishi, Org. Lett., 10, 4311 (2008); doi:10.1021/ol8017566.
  2. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 16, 4467 (1975); doi:10.1016/S0040-4039(00)91094-3.
  3. V.P.W. Bohm and W.A. Herrmann, Eur. J. Org. Chem., 3679 (2000); doi:10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.CO;2-X.
  4. D. Mery, K. Heuze and D. Astruc, Chem. Commun., 15, 1934 (2003); doi:10.1039/b305391c.
  5. A. Elangovan, Y. Wang and T.-I. Ho, Org. Lett., 5, 1841 (2003); doi:10.1021/ol034320+.
  6. B. Liang, M. Dai, J. Chen and Z. Yang, J. Org. Chem., 70, 391 (2005); doi:10.1021/jo048599z.
  7. Y. Liang, Y. Xie and J. Li, J. Org. Chem., 71, 379 (2006); doi:10.1021/jo051882t.
  8. A. Bernthsen, Ber. Deut. Chem. Ges., 20, 942 (1887); doi:10.1002/cber.188702001214.
  9. H. Brockmann, The Chemistry of Natural Product, Butterworths Publishers and Co. Ltd, London p. 405 (1961).
  10. T. Shimamoto, A. Tomoda, R. Ishida and K. Ohyashiki, Am. Assoc. Cancer Res., 7, 704 (2001).
  11. M.R. Lewis, P.P. Goland and H.A. Sloviter, Cancer Res., 9, 736 (1949).
  12. J.K. Horton, K.N. Thimmaiah, F.C. Harwood, J.F. Kuttesch and P.J. Houghton, Mol. Pharmocol. Abstr., 44, 552 (1993).
  13. B. Boothroyd and E.R. Clark, J. Chem. Soc., 1499 (1953); doi:10.1039/jr9530001499.
  14. T.U.S. Chu Daniel, Chem. Abstr., 104, 109663k (1986).
  15. T. Yuasa, Ann. Res. Inst. Tuberc., 11, 265 (1953).
  16. W.P. Rogers, J. Cymerman-Craig and G.P. Warwick, Br. J. Pharmacol., 10, 340 (1955); doi:10.1111/j.1476-5381.1955.tb00880.x.
  17. S. Gao, T. Takano, H.J. Sadak, C. Noda, N. Hori-Tamura, A. Tomoda and H. Yamamura, Br. J. Pharmacol., 137, 749 (2002); doi:10.1038/sj.bjp.0704939.
  18. A. Ribbentrop and N. Schauwann, Arch. Int. Pharmacodyn. Ther., 149, 374 (1964).
  19. P.N. Craig, Chem. Abstr., 55, 582 (1960); US Patent 2,947,747 (1961)..
  20. H.B. Rickert and W.M. Geiger, US Patent 2,945, 856 (1960).
  21. C.M. Murphy, H. Ravner and N.L. Smith, Ind. Eng. Chem., 42, 2479 (1950); doi:10.1021/ie50492a027.
  22. W.C. Holmes and A.R. Peterson, Stain Technol., 6, 79 (1931).
  23. W.C. Holmes, Amer. Dye Stuff Rept, 17, 626 (1929).
  24. G. Mannelli and E. Martiini, Ann. Chim. (Rome), 41, 68 (1951).
  25. S. Musha and T. Kitagawa, Chem. Abstr., 51, 127737 (1957).
  26. E. Ruzioka, Chem. Commun., 24, 930 (1964).
  27. E. Ruzioka, Abstract, 51, 1193 (1957).
  28. E. Ruzioka, Chem. Listy, 51, 969 (1959).
  29. N. Didry, M. Pinkas, and L. Dubreil, Ann Pharm., 44, 73 (1986).
  30. V.D. Kerkar, R.B. Mhaske, P.L. Kulkarni and A.R. Kulkarni, J. Pharm. Soc., 49, 184 (1987).
  31. V.P. Papageorgiou, A.N. Assimopoulou, E.A. Couladouros, D. Hepworth and K.C. Nicolaou, Angew. Chem. Int., 38, 270 (1999); doi:10.1002/(SICI)1521-3773(19990201)38:3<270::AID-ANIE270>3.0.CO;2-0.
  32. R.F. Silver and H.L. Holmes, Can. J. Chem., 46, 1859 (1968); doi:10.1139/v68-309.
  33. H. Tomozane, Y. Takeuchi, T. Choshi, S. Kishida and M. Yamato, Chem. Pharm. Bull.(Tokyo), 80, 925 (1990); doi:10.1248/cpb.38.925.
  34. C.K. Ryc, J.C. Ryu, C.Y. Chung and D.H. Kim, Proceeding Internal Congress of New Drug Development of the Pharmaceutical Society in Commemoration of the Society 40th Anniversary (1990).
  35. E.M. Hodnett, C. Wongwiechintana, W.J. Dunn and P. Marrs, J. Med. Chem., 26, 570 (1983); doi:10.1021/jm00358a021.
  36. T.S. Lin, L.Y. Zhu, S.P. Xu, A. Divo and A. Sartorelli, J. Med. Chem., 34, 1643 (1991); doi:10.1021/jm00109a016.
  37. C.Y. Chung, C.K. Ryu, J.C. Ryu and D.H. Kim, Proceedings of the Spring Convention of the Pharmaceutical Society, 34, 125 (1990).
  38. Y. Take, M. Sawada, H. Kunai, Y. Inouye and S. Nakamura, J. Antibiotics, 39, 557 (1986); doi:10.7164/antibiotics.39.557.
  39. T. Ngoc-Chau and N. Minh-Trile, Sciforum Electronic Conference Series, 13, c012 (2009).
  40. T.G. Emori and R.P. Gaynes, Clin. Microbiol. Rev., 6, 428 (1993); doi:10.1128/CMR.6.4.428.
  41. C.O. Okafor, Int. J. Rev. Commun. Heterocycl. Chem., 7, 392 (1977).
  42. C. Perez, M. Pauli and P. Bazerque, Acta Biol. Med. Exp., 15, 113 (1990).
  43. O.O. Ojo, A.O. Ajayi and I.I. Anibijuwon, J. Zhejiang Univ. Sci., 8, 189 (2007); doi:10.1631/jzus.2007.B0189.
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