Premium
3‐Aryl‐5‐[(aryloxy)methyl]‐3‐[(1 H ‐1,2,4‐triazol‐1‐yl)methyl]‐2‐methylisoxazolidine derivatives. Synthesis and antifungal activity
Author(s) -
Bennett Grace A.,
Swift Patricia A.,
Mullen George B.,
Allen Stanley D.,
Mitchell Jeffrey T.,
Jones Wendy E.,
Georgiev Vassil St.
Publication year - 1989
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570260639
Subject(s) - chemistry , ketoconazole , in vivo , aryl , potency , antifungal , stereochemistry , in vitro , yeast , biological activity , derivative (finance) , organic chemistry , biochemistry , microbiology and biotechnology , alkyl , biology , economics , financial economics
The synthesis and antifungal activity of a novel series of 3‐aryl‐5‐[(aryloxy)methyl]‐3‐[(1 H ‐1,2,4‐triazol‐1‐yl)‐methyl]‐2‐methylisoxazolidines are described. The in vitro activity was evaluated in solid agar cultures against a variety of dermatophytes and yeast fungi, while in vivo activity was measured in an immune‐compromised mouse model of systemic candidiasis. The activity of the title series was compared to that of ketoconazole and one derivative, the cis ‐3‐(4‐chlorophenyl)‐5‐(4‐chlorophenyloxy)methyl analogue 5f was found to possess a similar potency in the in vivo assay. Structure‐activity relationship correlations are also discussed.