Design, synthesis, in vitro antimicrobial and anticancer activity of novel methylenebis-isoxazolo[4,5-b]azepines derivatives

European Journal of Medicinal Chemistry

Volumn 50, Issue , 2012, Pages 344-349

  Rajanarendar, E ^a   Nagi Reddy, M ^a   Rama Krishna, S ^a   Govardhan Reddy, K ^a   Reddy, Y N ^a   Rajam, M V ^b  

^a KAKATIYA UNIVERSITY   (India)

^b UNIVERSITY OF DELHI   (India)

Author keywords

Antimicrobial and anticancer activities; Methylene bis isoxazolo 4,5 b azepine; Michael addition; Reductive cyclization

Indexed keywords

ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; AZEPINE DERIVATIVE; METHYLENEBIS (7,8 DIHYDRO 6H 3 METHYL 5 (2 HYDROXYPHENYL) 7 (2 HYDROXY PHENYL) ISOXAZOLO [4,5 B]AZEPINE; METHYLENEBIS (7,8 DIHYDRO 6H 3 METHYL 5 (4 CHLOROPHENYL) 7 (2 HYDROXY PHENYL)ISOXAZOLO[4,5 B]AZEPINE; METHYLENEBIS 7,8 DIHYDRO 6H 3 METHYL 5 (2 FURYL) 7 (2 HYDROXYPHENYL)ISOXAZOLO [4,5 B]AZEPINE; METHYLENEBIS 7,8 DIHYDRO 6H 3 METHYL 5 (2 THIENYL) 7 (2 HYDROXYPHENYL)ISOXAZOLO [4,5-B]AZEPINE; METHYLENEBIS 7,8 DIHYDRO 6H 3 METHYL 5 (4 BROMOPHENYL) 7 (2 HYDROXY PHENYL) ISOXAZOLO [4,5-B]AZEPINE; METHYLENEBIS 7,8 DIHYDRO 6H 3 METHYL 5 (4 METHOXYPHENYL) 7 (2 HYDROXY PHENYL)ISOXAZOLO [4,5 B]AZEPINE; METHYLENEBIS 7,8 DIHYDRO 6H 3 METHYL 5 (4 METHYLPHENYL) 7 (2 HYDROXY PHENYL)ISOXAZOLO[4,5 B]AZEPINE; METHYLENEBIS 7,8 DIHYDRO 6H 3 METHYL 5 (4 NITROPHENYL) 7 (2 HYDROXY PHENYL) ISOXAZOLO [4,5 B]AZEPINE; METHYLENEBIS 7,8 DIHYDRO 6H 3 METHYL 5 PHENYL 7 (2 HYDROXYPHENYL)ISOXAZOLO [4,5 B]AZEPINE; UNCLASSIFIED DRUG; ISOXAZOLE DERIVATIVE; METHYLENEBIS(7,8 DIHYDRO 6H 3 METHYL 5 (2 FURYL) 7 (2 HYDROXYPHENYL)ISOXAZOLO(4,5 B)AZEPINE); METHYLENEBIS(7,8 DIHYDRO 6H 3 METHYL 5 (2 THIENYL) 7 (2 HYDROXYPHENYL)ISOXAZOLO(4,5 B)AZEPINE); METHYLENEBIS(7,8-DIHYDRO-6H-3-METHYL-5-(2-FURYL)-7-(2-HYDROXYPHENYL)ISOXAZOLO(4,5-B)AZEPINE); METHYLENEBIS(7,8-DIHYDRO-6H-3-METHYL-5-(2-THIENYL)-7-(2-HYDROXYPHENYL)ISOXAZOLO(4,5-B)AZEPINE);

ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; BACTERIUM; BREAST TUMOR; CELL CULTURE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CYTOLOGY; DRUG EFFECT; FEMALE; KIDNEY; MICROBIOLOGICAL EXAMINATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; AZEPINES; BACTERIA; BREAST NEOPLASMS; CELL PROLIFERATION; CELLS, CULTURED; DRUG DESIGN; FEMALE; HUMANS; ISOXAZOLES; KIDNEY; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84858449642     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.02.013     Document Type: Article

References (24)

1. J.B. Gibbs Science 287 2000 1969
2. C. Unger Drug Future 22 1997 1337
3. P. Heffeter, M.A. Jakupec, W. Orner, S. Wild, N.G. Keyserlingk, L. Elbling, H. Zorbas, A. Korynevska, S. Knasmuller, H. Sutterluty, M. Micksche, B.K. Keppler, and W. Berger Biochem. Pharmacol. 71 2006 426
4. E. Menta, and M. Palumbo Exp. Opin. Ther. Patents 7 1997 1401
5. M.R. Boyd, and K.D. Paull Drug Dev. Res. 34 1995 91
6. C.J. Rao, and A.K. Murthy Indian J. Chem. 16B 1978 636
7. E. Rajanarendar, P. Ramesh, E. Kalyan Rao, G. Mohan, and M. Srinivas Arkivoc XIV 2007 266
8. P. Krogsgaard-Larsen, E. Falch, H. Pedersen, Eu. Patent. Appl. No. 88310276 (1988) (Chem Abstr).
9. J. Ignacio Andres, J. Alcazar, J.M. Alonso, A. Diaz, J. Fernandez, P. Gil, L. Itumino, E. Matesanz, T.F. Meert, A. Megens, and V.K. Sipido Bioorg. Med. Chem. Lett. 12 2 2002 243
10. C.J. Rao, A.K. Murhty, and P.V. Reddy Indian Drugs Pharm. Ind. 25 1981 265
11. C.J. Rao, A.K. Murthy, M.M. Reddy, and U.B. Swamy Indian Drugs Pharm. Ind. 1 1980 322
12. James Elliot Jeffs. Chem. Ind. (London) 27 1967 1175
13. H.A. Johnson, and N.R. Thomas Bioorg. Med. Chem. Lett. 12 2002 237
14. A. Sadanandam, M.V. Rajam, K. Subhash, and E. Rajanarendar Indian Bot. Report 3 1 1984 38
15. P.B. Reddy, S.M. Reddy, E. Rajanarendar, and A.K. Murthy Indian Phytopath 37 1984 369
16. E. Rajanarendar, Md. Afzal, and D. Karunakar Indian J. Chem. 43 B 2004 168
17. E. Rajanarendar, E.K. Rao, Firoz Pasha. Shaik, M. Nagi Reddy, and M. Srinivas J. Sulfur. Chem. 31 4 2010 263
18. E. Rajanarendar, M. Nagi Reddy, K. Rama Murthy, K. Govardhan Reddy, S. Raju, M. Srinivas, B. Praveen, and M.S. Rao Bioorg. Med. Chem. Lett. 20 2010 6052
19. C.S. Marvel, and N. Tarkoy J.Am. Chem.Soc. 79 1957 6001
20. A. Nagaraj, and J. Chs. Reddy Heterocycl. Chem. 44 2007 1181
21. G.T. Morgon, and H.B. Burgess J. Chem. Soc. 1921 699
22. M.J. Weinstein, and G.H. Nagman Antibiotics 1978 Elsevier Scientific Publishing Company Amsterdam p. 464
23. A.L. Barry, and C. Thornsbery J.P. Lennette, Manual of Clinical Microbiology 1981 American Society for Microbiology Washington, DC 561
24. M. Botta, S. Armaroli, D. Castagnolo, G. Fontana, P. Perad, and E. Bombardelli Bioorg. Med. Chem. Lett. 17 2007 1579