Synthesis of new 1-[2-azido-2-(2,4-dichlorophenyl)ethyl]-1H/-imidazoles and in vitro evaluation of their antifungal activity

被引：2

作者：

Chevreuil, Francis ^{[1
]}

Landreau, Anne ^{[1
]}

Seraphin, Denis ^{[1
]}

Larcher, Gerald ^{[2
]}

Bouchara, Jean-Philippe ^{[2
]}

Richomme, Pascal ^{[1
]}

机构：

[1] UFR Sci Pharmaceut & Ingn Sante, Lab SONAS, EA 921, F-49100 Angers, France

[2] CHU Angers, IFR Grp Etud Interact Hote Pathogene 149, F-49933 Angers 9, France

来源：

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2008年 / 23卷 / 05期

关键词：

antifungal agents; Candida albicans; Candida glabrata; conazole; azide; resistance; Aspergillus fumigatus; FUNGAL-INFECTIONS; AGENTS;

D O I：

10.1080/14756360802205133

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：

New 1-[2-azido-2-(2,4-dichlorophenyl)ethyl]-1H/-imidazole were synthesized by nucleophilic substitution of various tertiary alcohols with azide anion in presence of boron trifluoride-diethyl etherate. Their antifungal activity was evaluated against Candida albicans, Candida glabrata, Aspergillus fumigatus and an azole-resistant petite mutant of C. glabrata. Preliminary SAR results are discussed.

引用

页码：617 / 622

页数：6

共 22 条

[1]

Ablordeppey SY, 1999, CURR MED CHEM, V6, P1151

[2]

BAWDEN D, 1983, EUR J MED CHEM, V18, P91

[3] The discovery and process development of a commercial route to the water soluble prodrug, fosfluconazole [J].

Bentley, A ;

Butters, M ;

Green, SP ;

Learmonth, WJ ;

Macrae, JA ;

Morland, MC ;

O'Connor, G ;

Skuse, J .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (02) :109-112

[4] Mechanisms of azole resistance in petite mutants of Candida glabrata [J].

Brun, S ;

Bergès, T ;

Poupard, P ;

Vauzelle-Moreau, C ;

Renier, G ;

Chabasse, D ;

Bouchara, JP .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2004, 48 (05) :1788-1796

[5]

Chen Anne, 2005, Expert Opin Emerg Drugs, V10, P21, DOI 10.1517/14728214.10.1.21

[6] Synthesis of new isoxazoles and dihydroisoxazoles and in vitro evaluation of their antifungal activity [J].

Chevreuil, Francis ;

Landreau, Anne ;

Seraphin, Denis ;

Larcher, Gerald ;

Mallet, Sabine ;

Bouchara, Jean-Philippe ;

Richomme, Pascal .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2007, 22 (05) :563-569

[7] Synthesis and antifungal activity of new thienyl and aryl conazoles [J].

Chevreuil, Francis ;

Landreau, Anne ;

Seraphin, Denis ;

Larcher, Gerald ;

Bouchara, Jean-Philippe ;

Richomme, Pascal .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2006, 21 (03) :293-303

[8] Epidemiology of nosocomial fungal infections [J].

Fridkin, SK ;

Jarvis, WR .

CLINICAL MICROBIOLOGY REVIEWS, 1996, 9 (04) :499-&

[9] PREPARATION AND ANTIMYCOTIC PROPERTIES OF DERIVATIVES OF 1-PHENETHYLIMIDAZOLE [J].

GODEFROI, EF ;

HEERES, J ;

VANCUTSE.J ;

JANSSEN, PAJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1969, 12 (05) :784-&

[10] Synthesis of 4-substituted 4-arylpiperidines [J].

Harriman, GCB ;

Shao, JX ;

Luly, JR .

TETRAHEDRON LETTERS, 2000, 41 (46) :8853-8856

← 1 2 3 →