Solution-phase synthesis of novel Δ2-isoxazoline libraries via 1,3-dipolar cycloaddition and their antifungal properties

被引：89

作者：

Basappa ^{[1
]}

Sadashiva, MP ^{[1
]}

Mantelingu, K ^{[1
]}

Swamy, SN ^{[1
]}

Rangappa, KS ^{[1
]}

机构：

[1] Univ Mysore, Dept Studies Chem, Mysore 570006, Karnataka, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2003年 / 11卷 / 21期

关键词：

D O I：

10.1016/j.bmc.2003.08.007

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of novel imidazolyl substituted delta(2)-isoxazoline libraries are currently of high interest. We report here in the full details of a study leading to the synthesis and antifungal activities of 3-(-2-butyl-4-chloro-1H-imidazolyl)-substituted delta(2)-isoxazolines. The solution phase synthesis of the title compounds was accomplished via 1,3-dipolar cycloaddition of in situ generated nitryl oxides from aldoximes with mono substituted alkenes to obtain the compound libraries contain an imidazole functionality in addition to the isoxazoline rings. The newly synthesized compounds when tested in vitro in solid agar culture exerted a potent antifungal activity against Aspergillus flavus, Fusarium moniliforme and Botrydiplodia theobromae also MIC values were determined. The title 5-substituted-3-imidazolyl-delta(2)-isoxazoline compounds represent a novel class of potent antifungal agents. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：4539 / 4544

页数：6

共 16 条

[1] KINETICS AND MECHANISM OF DIMERISATION OF BENZONITRILE N-OXIDES TO FURAZAN N-OXIDES [J].

BARBARO, G ;

BATTAGLIA, A ;

DONDONI, A .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (04) :588-+

[2]

Caramella P., 1984, 1 3 DIPOLAR CYCLOADD, V1, P337

[3] NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONISTS - THE DISCOVERY OF A SERIES OF N-(BIPHENYLYLMETHYL)IMIDAZOLES AS POTENT, ORALLY ACTIVE ANTIHYPERTENSIVES [J].

CARINI, DJ ;

DUNCIA, JV ;

ALDRICH, PE ;

CHIU, AT ;

JOHNSON, AL ;

PIERCE, ME ;

PRICE, WA ;

SANTELLA, JB ;

WELLS, GJ ;

WEXLER, RR ;

WONG, PC ;

YOO, SE ;

TIMMERMANS, PBMWM .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2525-2547

[4]

COLLINS CH, 1970, MICROB METHODS

[5]

Colton T, 1974, STAT MED

[6]

DORSWAMY HB, 2003, IN PRESS ANAL SCI

[7]

Elhance D.N., 1984, FUNDAMENTALS STAT

[8] KETOCONAZOLE - A REVIEW OF ITS THERAPEUTIC EFFICACY IN SUPERFICIAL AND SYSTEMIC FUNGAL-INFECTIONS [J].

HEEL, RC ;

BROGDEN, RN ;

CARMINE, A ;

MORLEY, PA ;

SPEIGHT, TM ;

AVERY, GS .

DRUGS, 1982, 23 (1-2) :1-36

[9]

Huisgen R., 1963, Angew. Chem. Int. Ed, V2, P565, DOI 10.1002/anie.196305651

[10]

Mallesha H, 2001, SYNTHESIS-STUTTGART, P2415

← 1 2 →