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Synthesis and Antifungal Activity of 1‐[(2‐Benzyloxy)Phenyl]‐2‐(Azol‐1‐yl)Ethanone Derivatives: Exploring the Scaffold Flexibility
Author(s) -
Emami Saeed,
KazemiNajafabadi Motahare,
Pashangzadeh Soughra,
Foroumadi Alireza,
Faramarzi Mohammad Ali,
Samadi Nasrin,
Falahati Mehraban,
Fateh Roohollah,
AshrafiKhozani Mahtab
Publication year - 2011
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2011.01243.x
Subject(s) - chemistry , azole , antifungal , fluconazole , combinatorial chemistry , stereochemistry , antifungal drug , hydrochloride , organic chemistry , microbiology and biotechnology , biology
Based on the N ‐(phenethyl)azole backbone of azole antifungals, we designed 1‐[(2‐benzyloxy)phenyl]‐2‐(azol‐1‐yl)ethanone derivatives 2 and 3 , containing benzyloxyphenyl scaffold of croconazole. Also these compounds can be considered as flexible analogs, resulted from C2–C3 disconnection of 3′‐chloro‐3‐imidazolylflavanone 1 , recently described as antifungal agent. Thus, in this report, we describe the synthesis of 1‐[(2‐benzyloxy)phenyl]‐2‐(azol‐1‐yl)ethanone derivatives 2 and 3 and their biological evaluation against different pathogenic fungi. By comparing the antifungal activity profile of flexible compounds 2 and 3 with that of rigid analog 1 , it can be inferred that lower susceptibilities (higher minimum inhibitory concentrations) were observed with flexible compounds. However, among the synthesized compounds, 1‐[2‐(2,4‐dichlorobenzyloxy)phenyl]‐2‐(1 H ‐imidazol‐1‐yl)ethanone hydrochloride ( 2g ) showed comparable or more potent antifungal activity in comparison with fluconazole as a standard drug.