Synthesis and anti-bacterial activity of some novel 2-(6-fluorochroman-2-yl)-1-alkyl/acyl/aroyl-1H-benzimidazoles

European Journal of Medicinal Chemistry

Volumn 41, Issue 5, 2006, Pages 599-604

  Kumar, Bobba Venkata Siva ^a,b   Vaidya, Sanjay Dashrath ^a   Kumar, Ramanatham Vinod ^a   Bhirud, Shekar Bhaskar ^a   Mane, Ramchandra Bhimrao ^b  

^a Glenmark Pharmaceuticals Limited   (India)

^b SHIVAJI UNIVERSITY   (India)

Author keywords

acylation; Alkylation; Antibacterial activity; Benzimidazole

Indexed keywords

2 (6 FLUOROCHROMAN 2 YL) 1 (4 BROMOBENZYL) 1H BENZIMIDAZOLE; 2 (6 FLUOROCHROMAN 2 YL) 1 (4 TERT BUTYLBENZYL) 1H BENZIMIDAZOLE; 2 (6 FLUOROCHROMAN 2 YL) 1 BENZENESULFONYL 1H BENZIMIDAZOLE; 2 (6 FLUOROCHROMAN 2 YL) 1 BENZYL 1H BENZIMIDAZOLE; 2 (6 FLUOROCHROMAN 2 YL) 1 BUTYL 1H BENZIMIDAZOLE; 2 (6 FLUOROCHROMAN 2 YL) 1 ETHYL 1H BENZIMIDAZOLE; 2 (6 FLUOROCHROMAN 2 YL) 1 METHYL 1H BENZIMIDAZOLE; 2 (6 FLUOROCHROMAN 2 YL) 1 PROPYL 1H BENZIMIDAZOLE; 2 (6 FLUOROCHROMAN 2 YL) 1 TOSYL 1H BENZIMIDAZOLE; 2 (6 FLUOROCHROMAN 2 YL) 1 TRIFLUOROMETHANESULFONYL 1H BENZIMIDAZOLE; 2 (6 FLUOROCHROMAN 2 YL) 1H BENZIMIDAZOLE; [2 (6 FLUOROCHROMAN 2 YL) 1H BENZIMIDAZOL 1 YL] PHENYL METHANONE; BENZIMIDAZOLE DERIVATIVE; ETHYL 2 (6 FLUOROCHROMAN 2 YL) 1H BENZIMIDAZOLE 1 CARBOXYLATE; TERT BUTYL 2 (6 FLUOROCHROMAN 2 YL) 1H BENZIMIDAZOLE 1 CARBOXYLATE; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; CHROMAN DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; POLYMERIZATION; SALMONELLA TYPHIMURIUM; ACYLATION; ALKYLATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ELECTROSPRAY MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSICAL CHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ACYLATION; ALKYLATION; ANTI-BACTERIAL AGENTS; BENZIMIDAZOLES; CHEMISTRY, PHYSICAL; CHROMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SALMONELLA TYPHIMURIUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646948894     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2006.01.006     Document Type: Article

References (15)

1. th Edition (2001), Merck & Co. Inc., NJ. P-1785, Monograph Number 10074
2. (a) J.B. Wright, Chem. Rev., 48 (1951) 397-541; (b) M. Amari, M. Fodili, B. Nedjar-Kolli, J. Heterocyclic Chem. 39 (2002) 811-816.
3. Kohler P. Int. J. Parasitol. 31 (2001) 336-339
4. Preston P.N. Chem. Rev. 74 (1974) 279-314
5. (a) H.J. Breslin, T.A. Miskowski, M.J. Kukla, H.L. De Winter, M.V. F. Somers, P.W.M. Roevens, R.W. Kavash, Bioorg. Med. Chem. Lett., 13(24) (2003) 4467-4471; (b) A.A. Spasov, L.N. Yozhitsa, L.I. Bugaeva, V.A. Anisimova, Pharmaceutical Chemistry Journal, 33(5) (1999) 232-242; (c) J. Valdez, R. Cedillo, A. Hernandez-Campos, L. Yepez, F. Hernandez-Luis, G. Navarrete-Vazquez, A. Tapia, R. Cortes, M. Hernandezc, R. Castillo, Bioorg. Med. Chem. Lett. 12 (2002) 2221-2224.
6. (a) K.C. Joshi, S. Giri, J. Indian Chem. Soc, 39(3) (1962) 185-187; (b) R.A. Appleon, J.R. Bantick, T.R. Chamberlain, D.N. Hardern, T.B. Lee, J. Med. Chem., 20(3) (1977) 371-379; (c) G.H. Ladouceur, R.D. Connell, J. Baryza, A-M. Campbell, T.G. Lease, G. Timothy, J.H. Cook, WO 99 32, 475 (1999), Chem. Abstr 131 (1999) 73558w.
7. (a) V.L.G.R. Eugene, D.B.M.F. Leopold, S.M.F. Josephin, EP0145067, (1985); Chem. Abstr: 104 (1985) 5773; (b) W. McNeely, Drugs, 57 (1999) 633-651; (c) A. Van de Water, J. Cardiovasc. Pharmacol.,11, (1988) 552-563.; (d) G.V. Lommen, J. Pharm. Belg. 45 (1990) 355-360.
8. S. Kii-chi, B. Masatoshi, S. Makoto, H. Chihiro, M. Kuniharu, EP719556 (1996), Chem. Abstr: 125 (1996) 96139a; (b) K. Masayasu, B. Yukata, T. Yamaguchi, R. Unno, H. Kimura, H. Inagaki, T. Noboru, T. Suzuki, B. Masatoshi, EP595183, (1994), Chem. Abstr: 121 (1994) 57539d; (c) M. A. Yorek, L. J. Coppey, J. S. Gellett, E. P. Davidson, D. D. Lund, Exp. Diabesity Res. 5 (2) (2004) 123-128.
9. Vaidya S.D., Siva Kumar B.V., Vinod Kumar R., Bhirud S.B., and Mashelkar U.C. Indian J. Heterocyclic Chem. 14 (2005) 197-200
10. R. Vinod Kumar, K. Raja Gopal, K.V.S.R. Seshu Kumar, J. Heterocyclic Chem., 42 (2005) 1405-1408; R. Vinod Kumar, K.V.S.R. Seshu Kumar, K. Raja Gopal, J. Heterocyclic Chem. 42 (2005) 153-156.
11. Phillips M.A. J. Chem. Soc. (1928) 2393-2399
12. Eaton P.E., Carlson G.R., and Lee J.T. J. Org. Chem. 38 (1973) 4071-4073
13. Kauffman J.M., Khalaj A., Litak P.T., Novinski J.A., and Bajwa G.S. J. Heterocyclic Chem. 31 4 (1994) 957-965
14. Reviews on microwave chemistry include: (a) C. Gabriel, S. Gabriel, E.H. Grant, B.S.J. Halstead, D.M.P. Mingos, Chem. Soc. Rev., 27 (1998) 213-224; (b) N. Kuhnert, Angew. Chem. Int. Ed. Eng., 41 (2002)1863-1866; (c) P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron, 57 (2001) 9225-9283; (d) A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault, D. Mathé, Synthesis 9 (1998)1213-1234; (e) S. A. Galema, Chem. Soc. Rev. 26 (1997) 233-238; (f) S. Caddick, Tetrahedron, 51 (1995) 10403-10432; (g) C.R. Strauss, R.W. Trainor, Aust. J. Chem., 48 (1995) 1665-1672; (h) Microwaves in Organic Synthesis, T.N. Danks, Tet. Lett., 40 (1999) 3957-; (i), A. Loupy, Ed.; Microwaves in Organic Synthesis. Wiley VCH: Weinheim, (2002).
15. (a) R.C. Elderfield, V.B. Meyer, J. Am. Chem. Soc., 76 (1954) 1891-1893; (b) G.W.H. Cheeseman, J. Chem. Soc., (1955) 3308-3310; (c) H. Irving, O. Weber, J. Chem. Soc. (1959) 2296-2298.