Stereoselective Synthesis and in Vitro Antifungal Evaluation of (E)- and (Z)-Imidazolylchromanone Oxime Ethers

A series of (E)‐ and (Z)‐2, 3‐dihydro‐3‐(1H‐imidazol‐1‐yl)‐4H‐1‐benzopyran‐4‐one oxime ethers have been synthesized and tested for antifungal activity. Most compounds showed moderate to potent in vitro antifungal activity. Among the tested compounds, compound (E)‐3d was the most active agent against...

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Bibliographic Details
Published in:Archiv der Pharmazie (Weinheim) 2002-07, Vol.335 (7), p.318-324
Main Authors: Emami, Saeed, Falahati, Mehraban, Banifatemi, Ali, Moshiri, Kayvan, Shafiee, Abbas
Format: Article
Language:English
Subjects:
1H-Imidazole
Antifungal activity
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Aspergillus niger - drug effects
Candida albicans - drug effects
Chromanone oxime ethers
Chromans - chemical synthesis
Chromans - chemistry
Chromans - pharmacology
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Microsporum - drug effects
Molecular Structure
Stereoisomerism
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Summary:A series of (E)‐ and (Z)‐2, 3‐dihydro‐3‐(1H‐imidazol‐1‐yl)‐4H‐1‐benzopyran‐4‐one oxime ethers have been synthesized and tested for antifungal activity. Most compounds showed moderate to potent in vitro antifungal activity. Among the tested compounds, compound (E)‐3d was the most active agent against Candida albicans and Aspergillus niger, and compounds (Z)‐(3a) and (E)‐3a were the most potent compounds against Microsporum gypseum. Detailed stereoselective synthesis, spectroscopic, and biological data are reported.
ISSN:0365-6233
1521-4184
DOI:10.1002/1521-4184(200209)335:7<318::AID-ARDP318>3.0.CO;2-O