Synthesis of novel 3-[5-ethyl-2-(2-phenoxy-ethyl)-pyridin]-5-substituted isoxazoline libraries via 1,3-dipolar cycloaddition and evaluation of antimicrobial activities

Medicinal Chemistry Research

Volumn 15, Issue 7-8, 2007, Pages 407-417

  Gaonkar, S L ^a   Lokanatha Rai, K M ^a   Prabhuswamy, B ^a  

^a UNIVERSITY OF MYSORE   (India)

Author keywords

1,3 dipolar cycloaddition; Antimicrobial activity; Chloramine T; Isoxazolines

Indexed keywords

2 [2 (4 (5 BENZOL(1,3)DIOXOL 5 YLMETHYL 4,5 DIHYDROISOXAZOL 3 YL)PHENOXY)ETHYL] 5 ETHYLPYRIDINE; 2, 2 [4 (5 (3,4 DIMETHOXYBENZYL)4,5 DIHYDROISOXAZOL 3 YL)PHENOXY]ETHYL 5 ETHYLPYRIDINE; 3 [4 (2 (5 ETHYLPYRIDIN 2 YL) ETHOXY)PHENYL] 4,5 DIHYDROISOXAZOLE 5 CARBONITRILE; 3 [4 (2 (5 ETHYLPYRIDIN 2 YL)ETHOXY)PHENYL] 4,5 DIHYDROISOXAZOL 5 CAROXYLIC ACID ETHYL ESTER; 3 [4 (2 (5 ETHYLPYRIDIN 2 YL)ETHOXY)PHENYL] 4,5 DIHYDROISOXAZOL 5 CAROXYLIC ACID METHYL ESTER; 4 [2 (5 ETHYLPYRIDYL)ETHOXY]BENZALDOXIME; 4 [3 (4 (2 (5 ETHYLPYRIDIN 2 YL)ETHOXY)PHENYL) 4,5 DIHYDROISOXAZOL 5 YLMETHYL] 2 METHOXY PHENOL; [3 (4 (2 (5 ETHYLPYRIDIN 2 YL) ETHOXY)PHENYL) 4,5 DIHYDROISOXAZOLE 5 YL]METHANOL; ALDOXIME; ALKENE; ISOXAZOLINE DERIVATIVE; NITRILE OXIDE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CHEMISTRY; CYCLOADDITION; DRUG SCREENING; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; STANDARD; X RAY CRYSTALLOGRAPHY;

EID: 34948891969     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-006-0015-z     Document Type: Article

References (18)

1. 2-isoxazoline libraries via 1,3-dipolar cycloaddition and their antifungal properties. Bioorg Med Chem 11:4539
2. 2 inhibitors. Bioorg Med Chem Lett 14:3679
3. 2-isoxazoline derivatives and their pharmacological characterization as β-adrenergic receptor antagonists. Bioorg Med Chem 16:401
4. Gaonkar SL, Yathirajan HS, Lokanatharai KM, Nagaraj B, Bolte M (2005) 4-[2-(5-Ethylpyridin-2-yl)ethoxy]benzaldehyde oxime. Acta Cryst E 61:751
5. Gaonkar SL, Rai KML, Prabhuswamy B (2006) Synthesis and antimicrobial studies of a new series of 2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-5- substituted-1,3,4-oxadiazoles. Eur J Med Chem 41: 841
6. Groutas WC, Chong LS, Epp JB, Venkataraman R, Brubaker MJ, Stanga MA, Kim EH, Keller CE (1992) Inhibition of human leukocyte elastase and cathepsin G by isoxazoline derivatives. Bioorg Med Chem Lett 2:1571
7. Groutas WC, Venkataraman R, Chong LS, Yoder JE, Epp JB, Stanga MA, Kim EH (1995) Isoxazoline derivatives as potential inhibitors of the proteolytic enzymes human leukocyte elastase, cathepsin G and proteinase 3: a structure-activity relationship study. Bioorg Med Chem 3:125
8. Hassner A, Lokanatha Rai KM (1989) A new method for the generation of nitrile oxides and its application to the synthesis of 2-isoxazolines. Synthesis 57
9. Kai H, Matsumoto H, Hattori N, Takase A, Fujiwara T, Sugimoto H (2001) Anti-influenza virus activities of 2-Alkoxyimino-N-(2-isoxazolin-3- ylmethyl)acetamides. Bioorg Med Chem 299 Lett 11:1997
10. Lednicer D, Mitscher LA (1998a) The organic chemistry of drug synthesis: Volume 1. John Wiley & Sons, New York: pp: 253-256
11. Lednicer D, Mitscher LA (1998b) The organic chemistry of drug synthesis: Volume 2. John Wiley & Sons, New York: pp. 278-283
12. Lednicer D, Mitscher LA (1998c) The organic chemistry of drug synthesis: Volume 3. John Wiley & Sons, New York: pp: 145-152
13. Lemriss S, Marquet B, Ginestet H, Lefeuvre L, Fassouane A, Boiron P (2003) Screening of new antifungal compounds in a collection of chemical products. J Mycol Med 13:189
14. Levin JI, Chan PS, Coupet J, Bailey TK, Vice G, Thibault L, Lai F, Venkatesan AM, Cobuzzi (1994) A 6-isoxazolinyl and isoxazolidinyl substituted quinazolinones as angiotensin II receptor antagonists. Bioorg Med Chem Lett 4:1703
15. Meguro K, Fujita T (1986) Process for preparing thiazolidine derivatives. Eur Patent 193256
16. Sielecki TM, Liu J, Mousa SA, Racanelli AL, Hausner EA, Wexler RR, Olson RE (2001) Synthesis and pharmacology of modified amidine isoxazoline glycoprotein IIb/IIIa receptor antagonists. Bioorg Med Chem Lett 11:2201
17. Srivastava S, Bajpai LK, Batra S, Bhaduri AP, Maikhuri JP, Gupta G, Dhar JD (1999) In search of new chemical entities with spermicidal and anti-HIV activities. Bioorg Med Chem 7:2607
18. Zgoda JR, Porter JR (2001) A convenient Microdilution method for screening natural products against bacteria and fungi. Pharm Biol 39:221