Issue

Vol. 25 No. 11 (2013): Vol 25 Issue 11

Copyright (c) 2013 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Biological Activity of Some 3-Aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines/6-bromo-3-aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines

https://doi.org/10.14233/ajchem.2013.14091
Davender Kumar Shukla
University School of Basic & Applied Sciences, Guru Gobind Singh Indraprastha University, Sector 16C, Dwarka, New Delhi-110 078, India
Manju Rani
University School of Basic & Applied Sciences, Guru Gobind Singh Indraprastha University, Sector 16C, Dwarka, New Delhi-110 078, India
Arif Ali Khan
University School of Basic & Applied Sciences, Guru Gobind Singh Indraprastha University, Sector 16C, Dwarka, New Delhi-110 078, India
Kavita Tiwari
University School of Biotechnology, Guru Gobind Singh Indraprastha University, Sector 16C, Dwarka, New Delhi-110 078, India
Rajinder K. Gupta
University School of Biotechnology, Guru Gobind Singh Indraprastha University, Sector 16C, Dwarka, New Delhi-110 078, India

Corresponding Author(s) : Arif Ali Khan

khanaarif@hotmail.com

Asian Journal of Chemistry, Vol. 25 No. 11 (2013): Vol 25 Issue 11

Abstract

N-(2-Hydroxy)-benzyl-arylamine (1) gives substantially pure 3-aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines/6-bromo-3-aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines (2) on cyclization with formaldehyde in methanol within 0.5-1.0 h at 65-68 ºC in excellent yields. The compounds thus prepared were screened for their antimicrobial studies against Gram-positive bacteria (Staphylococcus aureus, MTCC 96) and Gram-negative bacteria (E. coli, MTCC 739). For estimating antifungal activity the organism used is Candida albicans. Minimum inhibitory concentration of all the compounds was determined using the micro-broth dilution method.

Keywords

Arylamine Formaldehyde Cyclization Benz-1,3-oxazine Heterocyclic
Kumar Shukla, D., Rani, M., Ali Khan, A., Tiwari, K., & K. Gupta, R. (2013). Synthesis and Biological Activity of Some 3-Aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines/6-bromo-3-aryl-3,4-dihydro-2H-benz[e]-1,3-oxazines. Asian Journal of Chemistry, 25(11), 5921–5924. https://doi.org/10.14233/ajchem.2013.14091
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. B.K. Banik, S. Samajdar and I. Banik, Tetrahedron Lett., 44, 1699 (2003).
  2. V.N. Yuskovets and B.A. Ivin, Tetrahedron Lett., 44, 5279 (2003).
  3. J.D. Butler, D.M. Solano, L.I. Robins, M.J. Haddadin and M.J. Kurth, J. Org. Chem., 73, 234 (2008).
  4. R. Pedrosa, C. Andrés, P. Mendiguchía and J. Nieto, J. Org. Chem., 71, 8854 (2006).
  5. W.J. Burke, J. Am. Chem. Soc., 71, 609 (1949).
  6. G. Maffii, G. Bianchi, P. Schiatti and B. Silvestrini, Br. J. Pharmacol., 16, 231 (1961).
  7. H. Kai, Y. Morioka, Y. Koriyama, K. Okamoto, Y. Hasegawa, M. Hattori, K. Koike, H. Chiba, S. Shinohara, Y. Iwamoto, K. Takahashi and N. Tanimoto, Bioorg. Med. Chem. Lett., 18, 6444 (2008).
  8. Y. Tabuchi, Y. Ando, H. Kanemura, I. Kawasaki, T. Ohishi, M. Koida, R. Fukuyama, H. Nakamuta, S. Ohta, K. Nishide and Y. Ohishi, Bioorg. Med. Chem., 17, 3959 (2009).
  9. A.I. Vovk, A.M. Shivanyuk, R.V. Bugas, O.V. Muzychka and A.K. Melnyk, Bioorg. Med. Chem. Lett., 19, 1314 (2009).
  10. S. Wang, Y. Li, Y. Liu, A. Lu and Q. You, Bioorg. Med. Chem. Lett., 18, 4095 (2008).
  11. X. Li, U.H. Manjunatha, M.B. Goodwin, J.E. Knox, C.A. Lipinski, T.H. Keller, C.E. Barry III and C.S. Dowd, Bioorg. Med. Chem. Lett., 18, 2256 (2008).
  12. J.B. Chylinska, M. Janowiec and T. Urbarnsky, Br. J. Pharmacol., 43, 649 (1971).
  13. G.P. Moloney, D.J. Craik and M.N. Iskander, J. Pharm. Sci., 81, 692 (1982).
  14. N.A. Shakil, A. Dhawan, N.K. Sharma, V. Kumar, S. Kumar, M. Bose, H.G. Raj, C.E. Olsen, A.L. Cholli, L.A. Samuelson, J. Kumar, A.C. Watterson, V.S. Parmar and A.K. Prasad, Indian J. Chem. Sect. B, 42, 1958 (2003).
  15. B.M. Gurupadayya, Y.N. Manohara and M. Gopal, Indian J. Heterocyl. Chem., 15, 113 (2005).
  16. H. Ishida and Y. Rodrriguez, Polymer, 36, 3151 (1995).
  17. Y.-X. Wang and H. Ishida, J. Appl. Polym. Sci., 86, 2953 (2002).
  18. W.J. Burque and C.W. Stephens, J. Am. Chem. Soc., 74, 1518 (1952).
  19. Y.-X. Wang and H. Ishida, Macromol., 33, 2839 (2000).
  20. J.H. Billman and L.C. Dorman, J. Med. Chem., 6, 701 (1963).
  21. A. Rivera, G.I. Gallo and M. Gayon, Synth. Commun., 24, 2081 (1994).
  22. M. Reddy, M.R. Madan and V. Rajeshwer, Heterocycl. Commun., 10, 429 (2004).
  23. E.M. Campi, W.R. Jackson, Q.J. McCubbin and A.E. Trnacek, J. Chem. Soc., Chem. Commun., 2763 (1994).
  24. A.R. Katritzky and Y.-J. Xu, J. Org. Chem., 67, 8234 (2002).
  25. W.J. Burke and C.W. Stephens, J. Am. Chem. Soc., 7, 1518 (1952).
  26. M. Noda, J. Org. Chem., 24, 1209 (1959).
  27. J.K. Seydel, K.J. Schaper, E. Wempe and H.P. Cordes, J. Med. Chem., 19, 483 (1976).
  28. N. Ueyama, T. Yanagisawa, T. Kawai, M. Sonegawa, H. Baba, S. Mochizuki, K. Kosakai and T. Tomiyama, Chem. Pharm. Bull., 42, 1841 (1994).
  29. A.K. Kumar, L.K.M. Rai and K.B. Umesha, Indian J. Heterocycl. Chem., 10, 79 (2000).
  30. S.J. Joglekar and S.D. Samant, J. Indian Chem. Soc., 65, 110 (1988)
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0