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The solid-state conformation of the topical antifungal agent O-naphthalen-2-yl N-methyl-N-(3-methylphenyl)carbamothioate

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Large flat colorless needles of tolnaftate have been obtained from Tinactin, and have been shown to contain a 50:50 mixture of the (+ap,−sp,+ac,−ac) and (−ap,+sp,−ac,+ac) conformers. This finding fills a… Click to show full abstract

Large flat colorless needles of tolnaftate have been obtained from Tinactin, and have been shown to contain a 50:50 mixture of the (+ap,−sp,+ac,−ac) and (−ap,+sp,−ac,+ac) conformers. This finding fills a long-standing void in the structural chemistry of this classic antifungal compound, and suggests that prior theoretical models used to explain the spectroscopy, bioactivity, and mode of binding of tolnaftate to squalene epoxidase are probably inappropriate or suspect.

Keywords: solid state; conformation topical; antifungal agent; chemistry; state conformation; topical antifungal

Journal Title: Acta Crystallographica. Section C, Structural Chemistry
Year Published: 2018

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