New antifungal 1,2,4-triazoles with difluoro(heteroaryl)methyl moiety.
New 1,2,4-triazoles (1) having a difluoro(heteroaryl)methyl moiety were designed and synthesized via 1-aryl-2,2-difluoro-2-(heteroaryl)ethanones (2), which were prepared by two routes starting from the reaction of ethyl 2,2-difluoro(heteroaryl)acetate with phenyllithiums (Route A) and from the reaction of chlorodifluoro(heteroaryl)methane with benzaldehydes (Route B). The compounds 1 except for 1g show antifungal activities against yeasts and filamentous fungi in vitro, especially (+)-1f have equal or superior activities compared to those of itraconazole.
Central Research Labs, SS Pharmaceutical Co, Ltd, Narita, Chiba, Japan. Hiromichi.Eto@ssp.co.jp
H
H
Eto
Y
Y
Kaneko
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T
Sakamoto
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001231:Aspergillus flavus / Q000187:drug effects; D002175:Candida / Q000187:drug effects; D020005:Propanols / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000935:Antifungal Agents; D020005:Propanols; D014230:Triazoles; C045575:1,2,4-triazole