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A Green Approach to Synthesize and in vitro Antimicrobial Activity of Indeno-Imidazole Derivatives and Ninhydrin-Nucleophile Adducts
Corresponding Author(s) : Samia Rifat
Asian Journal of Chemistry,
Vol. 28 No. 7 (2016): Vol 28 Issue 7
Abstract
Ninhydrin (1) reacted with weak nitrogen nucleophiles (2a-2f) in the presence of H2O/EtOH medium to give the corresponding indeno-imidazole derivatives (3a-3d) and ninhydrin-nucleophile adducts (3e-3f). The structures of the compounds (3a-3f) were confirmed by their UV, IR, 1H NMR, 13C NMR spectra and elemental analyses. The synthesized compounds were evaluated for their antimicrobial activity by Kirby-Bauer disk diffusion method. Most of the compounds showed good to moderate antimicrobial activity.
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References
J.D. Hepworth, C.D. Gabbutt and B.M. Heron, in eds.: A.R. Katritzky, C.W. Rees and E.F. Scriven, In Comprehensive Heterocyclic Chemistry II: Pyrans and their Benzo Derivatives: Synthesis, Pergamon Press, Oxford, vol. 5 pp. 351-468 (1984).
M.R. Grimmett, Imidazole and Benzimidazole Synthesis, Academic Press (1997).
E.G. Brown, Ring Nitrogen and Key Biomolecules, Kluwer Academic Press (1998).
A.F. Pozharskii, A.T. Soldatenkov and A.R. Katritzky, Heterocycles in Life and Society, John Wiley & Sons, New York (1997).
L. Shargel, A.H. Mutnick, P.F. Souney and L.N. Swanson, Comprehensive Pharmacy Review, Lippincott Williams & Wilkins, edn 6, p. 930 (2006).
T. Castaño, A. Encinas, C. Pérez, A. Castro, N.E. Campillo and C. Gil, Bioorg. Med. Chem., 16, 6193 (2008); doi:10.1016/j.bmc.2008.04.036.
R.G. Bogle, G.S. Whitley, S.C. Soo, A.P. Johnstone and P. Vallance, Br. J. Pharmacol., 111, 1257 (1994); doi:10.1111/j.1476-5381.1994.tb14881.x.
R.M. Ghalib, R. Hashim, S.F. Alshahateet, S.H. Mehdi, O. Sulaiman, K.-L. Chan, V. Murugaiyah and A. Jawad, J. Chem. Crystallogr., 42, 783 (2012); doi:10.1007/s10870-012-0288-7.
R.M. Ghalib, R. Hashim, S.F. Alshahateet, S.H. Mehdi, O. Sulaiman, V. Murugaiyah and C.A. Aruldass, J. Mol. Struct., 1005, 152 (2011); doi:10.1016/j.molstruc.2011.08.042.
M. Chakrabarty, A. Mukherji, S. Arima, Y. Harigaya and G. Pilet, Monatsh. Chem., 140, 189 (2009); doi:10.1007/s00706-008-0066-6.
R.M. Shaker, A.F. Mahmoud and F.F. Abdel-Latif, J. Chil. Chem. Soc., 52, 563 (2005); doi:10.1002/jccs.200500083.
D.L. Pavia, G.M. Lampman and G.S. Kriz, Introduction to Spectroscopy, Thomson Brooks/Cole, edn 3 (2001).
H.H. Otto and J. Triepel, Liebigs Ann. Chem., 1982 (1976); doi:10.1002/jlac.197619761106.
M.G.Ahmed, S.A.Ahmed, U.Q.R.Romman and M.K.Alam, J. Bangladesh Acad. Sci., 5, 13 (1981).
A.W. Bauer, W.M. Kirby, J.C. Sherris and M. Turck, Am. J. Clin. Pathol., 45, 493 (1966).