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Design, Synthesis and Antibacterial Activity of N-(3-((4-(6-(2,2,2-Trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-yl)amide Derivatives
Corresponding Author(s) : B. Siva Reddy
Asian Journal of Chemistry,
Vol. 33 No. 3 (2021): Vol 33 Issue 3
Abstract
A new series of N-(3-((4-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-yl)amide derivatives (10a-h)were synthesized by the reaction of 3-((4-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-amine (8) with various carboxylic acids in the presence of T3P catalyst. The reaction is usually furnished within 60 min with good isolated yields. Coupling of 6-(2,2,2-trifluoroethoxy) nicotinic acid (1) with Weinreb amine hydrochloride gave N-methoxy-N-methyl-6-(2,2,2-trifluoroethoxy) nicotinamide (2). Compound 3 was synthesized by the Grignard reaction of compound 2 with methylmagnesium bromide. Bromination of compound 3 with N-bromo succinamide to obtain 2-bromo-1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethan-1-one (4), which was reacted with 2-(3-(((benzyloxy)carbonyl)amino)oxetan-3-yl)acetic acid (5) gave 2-oxo-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl 2-(3-(((benzyloxy)carbonyl)amino)oxetan-3-yl)acetate (6). Compound 7 was synthesized by the cyclization of compound 6 with ammonium acetate. Finally, debenzylation of compound 7 gave 3-((4-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-amine (8). All the synthesized amide compounds were characterized by analytical spectral techniques, like 1H & 13C NMR and LCMS and also evaluated their antibacterial activity.
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References
Y. Rival, G. Grassy and G. Michel, Chem. Pharm. Bull. (Tokyo), 40,1170 (1992); https://doi.org/10.1248/cpb.40.1170
M.H. Fisher and A. Lusi, J. Med. Chem., 15, 982 (1972); https://doi.org/10.1021/jm00279a026
Y. Rival, G. Grassy, A. Taudou and R. Ecalle, Eur. J. Med. Chem., 26, 13 (1991); https://doi.org/10.1016/0223-5234(91)90208-5
T. Biftu, D. Feng, M. Fisher, G. Liang, X. Qian, A. Scribner, R. Dennis,S. Lee, P.A. Liberator, C. Brown, A. Gurnett, P.S. Leavitt, D. Thompson, J. Mathew, A. Misura, S. Samaras, T. Tamas, J.F. Sina, K.A. McNulty, C.G. McKnight, D.M. Schmatz and M. Wyvratt, Bioorg. Med. Chem.Lett., 16, 2479 (2006); https://doi.org/10.1016/j.bmcl.2006.01.092
Y. Katsura, S. Nishino, Y. Inoue, M. Tomoi and H. Takasugi, Chem.Pharm. Bull. (Tokyo), 40, 371 (1992); https://doi.org/10.1248/cpb.40.371
E. Abignente, P. De Caprariis, E. Fattorusso and L. Mayol, J. Heterocycl. Chem., 26, 1875 (1989); https://doi.org/10.1002/jhet.5570260664
G.C. Moraski, L.D. Markley, P.A. Hipskind, H. Boshoff, S. Cho, S.G. Franzblau and M.J. Miller, ACS Med. Chem. Lett., 2, 466 (2011); https://doi.org/10.1021/ml200036r
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K.S. Gudmundsson and B.A. Johns, Bioorg. Med. Chem. Lett., 17, 2735 (2007); https://doi.org/10.1016/j.bmcl.2007.02.079
Y. Maruyama, K. Anami, M. Terasawa, K. Goto, T. Imayoshi, Y. Kadobe and Y. Mizushima, Arzneimittel Forsch., 31, 1111 (1981).
N. Habersaat, R. Fröhlich and E.-U. Würthwein, Eur. J. Org. Chem., 2567 (2004); https://doi.org/10.1002/ejoc.200400057
M. Yamada, T. Yura, M. Morimoto, T. Harada, K. Yamada, Y. Honma, M. Kinoshita and M. Sugiura, J. Med. Chem., 39, 596 (1996); https://doi.org/10.1021/jm950610n
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C.W. Derstine, D.N. Smith and J.A. Katzenellenbogen, J. Am. Chem. Soc., 118, 8485 (1996); https://doi.org/10.1021/ja9614833
S. Ohta, T. Osaki, S. Nishio, A. Furusawa, M. Yamashita and I. Kawasaki, Tetrahedron Lett., 41, 7503 (2000);https://doi.org/10.1016/S0040-4039(00)01283-1
P.V. Frank, K.S. Girish and B. Kalluraya, J. Chem. Sci., 119, 41 (2007); https://doi.org/10.1007/s12039-007-0007-7