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Synthesis, Antibacterial and Antifungal Evaluation of Novel 3-(5-Phenyl[1,3,4]oxadiazol-2-yl]-3,4-dihydro-2H-benzo[e][1,3]oxazines
Corresponding Author(s) : B. Bharath Kumar Goud
Asian Journal of Chemistry,
Vol. 26 No. 14 (2014): Vol 26 Issue 14
Abstract
Various novel 3-(5-phenyl[1,3,4]oxadiazol-2-yl]-3,4-dihydro-2H-benzo[e][1,3]oxazines (5a-g) have been synthesized from 5-phenyl-[1,3,4]oxadiazol-2-ylamine (1) and different salicylaldehydes (2a-g) as starting materials and 2-[(5-phenyl[1,3,4]oxadiazol-2-ylimino)methyl]phenols (3a-g) and 2-[(5-phenyl[1,3,4]oxadiazol-2-ylamino)methyl]phenols (4a-g) as intermediates. The newly synthesized compounds after structural confirmation were used to screen their antibacterial, antifungal and nematicidal activities and some of these compounds have been found as potential antimicrobial agents.
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- M.P. Hutt, E.F. Elslager and L.M. Werbel, J. Heterocycl. Chem., 7, 511 (1970); doi:10.1002/jhet.5570070308.
- F.A. Omar, N.M. Mahfouz and M.A. Rahman, Eur. J. Med. Chem., 31, 819 (1996); doi:10.1016/02235234(96)83976-6.
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- A. Husain and M. Ajmal, Acta Pharm., 59, 223 (2009); doi:10.2478/v10007-009-0011-1.
- S.L. Gaonkar, K.M. Rai and B. Prabhuswamy, Eur. J. Med. Chem., 41, 841 (2006); doi:10.1016/j.ejmech.2006.03.002.
- M.A. Ali and M. Shaharyar, Bioorg. Med. Chem. Lett., 17, 3314 (2007); doi:10.1016/j.bmcl.2007.04.004.
- Z.H Luo, S.Y. He, B.Q. Chen, Y.P. Shi, Y.M. Liu, C.W. Li and Q.S. Wang, Chem. Pharm. Bull., 60, 887 (2012); doi:10.1248/cpb.c12-00250.
- V.J. Ram, U.K. Singha and P.Y. Guru, Eur. J. Med. Chem., 25, 533 (1990); doi:10.1016/0223-5234(90)90148-V.
- P.J. Shirote and M.S. Bhatia, Chin. J. Chem., 28, 1429 (2010); doi:10.1002/cjoc.201090244.
- V. Padmavathi, G. Sudhakar Reddy, A. Padmaja, P. Kondaiah and Ali-Shazia, Eur. J. Med. Chem., 44, 2106 (2009); doi:10.1016/j.ejmech.2008.10.012.
- B. Jayashankar, K.M. Lokanath Rai, N. Baskaran and H.S. Sathish, Eur. J. Med. Chem., 44, 3898 (2009); doi:10.1016/j.ejmech.2009.04.006.
- F.A. Omar, N.M. Mahfouz and M.A. Rahman, Eur. J. Med. Chem., 31, 819 (1996); doi:10.1016/0223-5234(96)83976-6.
- M. Adib, E. Sheibani, M. Mostofi, K. Ghanbary and H.R. Bijanzadeh, Tetrahedron, 62, 3435 (2006); doi:10.1016/j.tet.2006.01.048.
- N. Zanatta, A.M.C. Squizani, L. Fantinel, F.M. Nachtigall, D.M. Borchhardt, H.G. Bonacorso and A.P. Martins, J. Braz. Chem. Soc., 16(6a), 1255 (2005); doi:10.1590/S0103-50532005000700025.
- F.A.J. Kerdesky, Tetrahedron Lett., 46, 1711 (2005); doi:10.1016/j.tetlet.2005.01.048.
- C.W. McBeth and G.B. Bergeson, Phytopathology, 43, 264 (1953).
- National Committee for Clinical Laboratory Standards (NCCLS), Standard methods for dilution antimicrobial susceptibility tests for bacteria, Nat. Comm. Lab. Stands, Villanova, 242 (1982).
References
M.P. Hutt, E.F. Elslager and L.M. Werbel, J. Heterocycl. Chem., 7, 511 (1970); doi:10.1002/jhet.5570070308.
F.A. Omar, N.M. Mahfouz and M.A. Rahman, Eur. J. Med. Chem., 31, 819 (1996); doi:10.1016/02235234(96)83976-6.
A. Zarghi, S.A. Tabatabai, M. Faizi, A. Ahadian, P. Navabi, V. Zanganeh and A. Shafiee, Bioorg. Med. Chem. Lett., 15, 1863 (2005); doi:10.1016/j.bmcl.2005.02.014.
A. Husain and M. Ajmal, Acta Pharm., 59, 223 (2009); doi:10.2478/v10007-009-0011-1.
S.L. Gaonkar, K.M. Rai and B. Prabhuswamy, Eur. J. Med. Chem., 41, 841 (2006); doi:10.1016/j.ejmech.2006.03.002.
M.A. Ali and M. Shaharyar, Bioorg. Med. Chem. Lett., 17, 3314 (2007); doi:10.1016/j.bmcl.2007.04.004.
Z.H Luo, S.Y. He, B.Q. Chen, Y.P. Shi, Y.M. Liu, C.W. Li and Q.S. Wang, Chem. Pharm. Bull., 60, 887 (2012); doi:10.1248/cpb.c12-00250.
V.J. Ram, U.K. Singha and P.Y. Guru, Eur. J. Med. Chem., 25, 533 (1990); doi:10.1016/0223-5234(90)90148-V.
P.J. Shirote and M.S. Bhatia, Chin. J. Chem., 28, 1429 (2010); doi:10.1002/cjoc.201090244.
V. Padmavathi, G. Sudhakar Reddy, A. Padmaja, P. Kondaiah and Ali-Shazia, Eur. J. Med. Chem., 44, 2106 (2009); doi:10.1016/j.ejmech.2008.10.012.
B. Jayashankar, K.M. Lokanath Rai, N. Baskaran and H.S. Sathish, Eur. J. Med. Chem., 44, 3898 (2009); doi:10.1016/j.ejmech.2009.04.006.
F.A. Omar, N.M. Mahfouz and M.A. Rahman, Eur. J. Med. Chem., 31, 819 (1996); doi:10.1016/0223-5234(96)83976-6.
M. Adib, E. Sheibani, M. Mostofi, K. Ghanbary and H.R. Bijanzadeh, Tetrahedron, 62, 3435 (2006); doi:10.1016/j.tet.2006.01.048.
N. Zanatta, A.M.C. Squizani, L. Fantinel, F.M. Nachtigall, D.M. Borchhardt, H.G. Bonacorso and A.P. Martins, J. Braz. Chem. Soc., 16(6a), 1255 (2005); doi:10.1590/S0103-50532005000700025.
F.A.J. Kerdesky, Tetrahedron Lett., 46, 1711 (2005); doi:10.1016/j.tetlet.2005.01.048.
C.W. McBeth and G.B. Bergeson, Phytopathology, 43, 264 (1953).
National Committee for Clinical Laboratory Standards (NCCLS), Standard methods for dilution antimicrobial susceptibility tests for bacteria, Nat. Comm. Lab. Stands, Villanova, 242 (1982).