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Synthesis and Biological Evaluation of Novel Series of 3-Substituted 2-Methoxy-6-(5-phenyl-[1,3,4]oxadiazol-2-yl)pyridine Derivatives as Antimicrobial Agents
Corresponding Author(s) : B. Bharath Kumar Goud
Asian Journal of Chemistry,
Vol. 27 No. 12 (2015): Vol 27 Issue 12
Abstract
A series of novel 2-methoxy-3-phenyl-6-(5-phenyl-[1,3,4]oxadiazol-2-yl)pyridine (6a-h) have been synthesized from bromo methoxy picoline as starting material. Finally, oxadiazoles were coupled with various boronic acids using Suzuki coupling reactions to give the target compounds. The newly synthesized compounds were evaluated for their efficacy as antimicrobial agents against various Gram-positive and Gram-negative strains of bacteria and fungal strains. Compounds 6g and 6h possessing fluoro groups at second and fourth positions of the aniline ring exhibited broad spectrum inhibition against all the strains tested. Moreover, other compounds also found to be potential fungal agents in comparison to the standard drugs.
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References
M.L. Behnke, PCT Int. Appl., 2009126691 (2009).
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.
V. Padmavathi, G.S. Reddy, A. Padmaja, P. Kondaiah and A. 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.
Z.-H. Xiao, Huaxue Shiji, 30, 415 (2008).
T. Asberom, PCT Tnt. Appl., 2005097768 (2005).
B. Trivedi, PCT Int. Appl., 2012076989 (2012).
M. Christakakou, M. Schön, M. Schnürch and M.D. Mihovilovic, Synlett, 24, 2411 (2013); doi:10.1055/s-0033-1339870.
X.J. Ren, Youji Huaxue, 29, 1147 (2009).
C.D. Pan, M.C. Liu, L. Zhang, H.Y. Wu, J.C. Ding and J. Cheng, Catal. Commun., 9, 508 (2008); doi:10.1016/j.catcom.2007.06.022.
M.P. Hutt, E.F. Elslager and L.M. Werbel, J. Heterocycl. Chem., 7, 511 (1970); doi:10.1002/jhet.5570070308.
S.L. Gaonkar, K.M. Rai and B. Prabhuswamy, Eur. J. Med. Chem., 41, 841 (2006); doi:10.1016/j.ejmech.2006.03.002.
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.
S. Vuoti, J. Autio, M. Laitila, M. Haukka and J. Pursiainen, Eur. J. Inorg. Chem., 397 (2008); doi:10.1002/ejic.200700705.
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.
National Committee for Clinical Laboratory Standards (NCCLS), Standard Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria, Nat. Comm. Lab. Stands, Villanova, p. 242 (1982).