Design, synthesis, antimicrobial, anti-inflammatory, and analgesic activity of novel dihydrobenzo furo[3,2-e]isoxazolo[4,5-b]azepin-5(5aH)-ones

Medicinal Chemistry Research

Volumn 22, Issue 12, 2013, Pages 6143-6153

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

^a KAKATIYA UNIVERSITY   (India)

^b UNIVERSITY OF DELHI   (India)

Author keywords

Analgesic activity; Anti inflammatory activity; Antimicrobial activity; Dihydrobenzofuro 3,2 e isoxazolo 4,5 b azepin 5(5aH) ones; Reductive cyclization

Indexed keywords

3 METHYL 10B,11 DIHYDRO 4H BENZOFURO[3,2 E]ISOXAZOLO [4,5 B]AZEPIN 5(5AH) ONE; 3,9 DIMETHYL 10B,11 DIHYDRO 4H BENZOFURO[3,2 E]ISOXAZOLO[4,5 B]AZEPIN 5(5AH) ONE; 7,9 DIBROMO 3 METHYL 10B,11 DIHYDRO 4H BENZOFURO[3,2E]ISOXAZOLO[4,5 B]AZEPIN 5(5AH) ONE; 7,9 DICHLORO 3 METHYL 10B,11 DIHYDRO 4H BENZOFURO[3,2 E] ISOXAZOLO[4,5 B]AZEPIN 5(5AH) ONE; 9 BROMO 3 METHYL 10B,11 DIHYDRO 4H BENZOFURO[3,2 E]ISOXAZOLO[4,5 B]AZEPIN 5(5AH) ONE; 9 CHLORO 3 METHYL 10B,11 DIHYDRO 4H BENZOFURO[3,2 E] ISOXAZOLO[4,5 B]AZEPIN 5(5AH) ONE; 9 METHOXY 3 METHYL 10B,11 DIHYDRO 4H BENZOFURO[3,2 E] ISOXAZOLO[4,5 B]AZEPIN 5(5AH) ONE; ANALGESIC AGENT; ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; AZEPINE DERIVATIVE; CIPROFLOXACIN; DICLOFENAC; DIHYDROBENZOFURAN DERIVATIVE; FLUCONAZOLE; ISOXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SPHAERICUS; BACILLUS SUBTILIS; COLLETOTRICHUM CAPSICI; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; FUSARIUM OXYSPORUM; MOUSE; NONHUMAN; RAT; STAPHYLOCOCCUS AUREUS; THANATEPHORUS CUCUMERIS; VERTICILLIUM DAHLIAE;

EID: 84886094095     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0598-0     Document Type: Article

References (22)

1. Abd-Elazem IS, Chen HS, Bates RB, Huang RC (2002) Isolation of two highly potent and non-toxic inhibitors of human immunodeficiency virus type 1 (HIV-1) integrase from Salvia miltiorrhiza. Antivir Res 55:91
2. Apers S, Vlietinck A, Pieters L (2003) Lignans and neolignans as lead compounds. Phytochem Rev 2:201
3. Chimichi S (1989) The preparation of coumaric acids via Styrylisoxazoles. Heterocycles 20:263-267
4. De Campos MP, Filho VC, Da Silva RZ, Yunes RA, Zacino S, Juarez S, Bella Cruz RC, Bella Cruz A (2005) Evaluation of antifungal activity of Piper solmsianum C. DC. var. solmsianum (Piperaceae). Biol Pharm Bull 28:1527
5. Krogsgaard-Larsen P, Falch E, Pedersen H (1988) Eu. Patent. Appl. No. 88310276
6. LaValle CR, Bravo-Altamirano K, Giridhar KV, Chen J, Sharlow E, Lazo JS, Pater W, Wang QJ (2010) Novel protein kinase D inhibitors cause potent arrest in prostate cancer cell growth and motility. BMC Chem Biol 10:1
7. Malla Reddy K, Rao CJ, Murthy AK (1981) Fused heterocycles IV. Synthesis of 7(O-hydroxyphenyl)-3,5-dimethyl 1-7,8-dihydro-6H-isoxazolo(4,5-b)azepines. Bull Chem Soc Jpn 54:361
8. Margery Linday E (1962) Practical introduction to microbiology. E. & F. N. Spon Ltd., New York, p 177
9. Martinez R (1980) The behaviour of 3-methyl-5-(o-r-styryl)-4- nitroisoxazoles under electron impact. I J Heterocyclic Chem 17:581-585
10. National committee for clinical laboratory standards (NCCLS) (1982) Standard methods for dilution antimicrobial susceptibility tests for bacteria, which grows aerobically; National committee for clinical laboratory standards Ltd. Villanova. 242
11. Pauletti PM, Araujo AR, Young MC, Giesbrecht AM, Bolzani VD (2000) Nor-Lignans from the leaves of Styrax ferrugineus (Styracaceae) with antibacterial and antifungal activity. Phytochemistry 55:597
12. Pieters L, Van Dyck S, Gao M, Bai R, Hamel E, Vlietinck A, Lemiere G (1999) Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit tubulin polymerization. J Med Chem 42:5475
13. Rajanarendar E, Nagi Reddy M, Rama Murthy K, Surendar P, Reddy RN, Reddy YN (2012a) Synthesis and in vitro and in vivo anticancer activity of novel phenylmethylene bis-isoxazolo[4, 5-b]azepinesBioorg. Med Chem Lett 22:149
14. Rajanarendar E, Raju S, Nagi Reddy M, Rama Krishna S, Hari Kiran L, Ram Narasimha Reddy A, Narasimha Reddy Y (2012b) Multi-component synthesis and in vitro and in vivo anticancer activity of novel arylmethylene bis-isoxazolo[4, 5-b]pyridine-N-oxides. Eu J Med Chem 50:274
15. Rajanarendar E, Nagi Reddy M, Govardhan Reddy K, Rama Krishna S (2012c) l-Proline catalyzed efficient one-pot three-component aza-Diels-Alder reactions on nitrostyryl isoxazoles: a facile synthesis of new isoxazolyl tetrahydroquinolines and isoxazolo[2, 3-a] pyrimidines. Tetrahedron Lett 53:2909
16. Rajanarendar E, Govardhan Reddy K, Rama Krishna S, Nagi Reddy M, Shireesha B, Durgaiah G, Reddy YN (2012d) Synthesis and in vitro and in vivo anticancer activity of novel 3-methyl-5H-isoxazolo[5′4′:5,6] pyrido[2,3-b]indoles. Bioorg Med Chem Lett 22:6677
17. Rao CJ, Murthy AK, Reddy PV (1981a) Mitotic inhibition & chromosomal damage induced by isoxazoloazepines in allium cepa meristematic cells. Indian Drugs Pharm Ind 25:265
18. Rao CJ, Murthy AK, Reddy MM, Swamy UB (1981b) Laboratary evaluation of isoxazoles against two pathogenic fungi-1: isoxazoloazepines. Indian Drugs Pharm Ind 1:322
19. Reddenna P, Whern J, Maddipati Reddy KR (1990) Purification of arachidonate 5-lipoxygenase from potato tubers. Methods Enzymol 187:268
20. Syamsudin F, Rahayn L (2010) HPLC analysis and pharmacokinetic study of mangostin after orally administration in rats. Int J Pharma Bio Sci 1(1):51-54
21. Ulusu NN, Ercil D, Salcar MK, Tezcan EE (2002) Abietic acid inhibits lipooxygenase activity. Phytother Res 16:88
22. Winter CA, Risley EA, Nuss GW (1990) Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs. Proc Soc Expt Biol Med 111:544-547