Syntheses of Organic Fluorine Compounds. III. : Studies on the Antifungal Substances belonging to the Fluorine Substituted p-Acylaminophenylthiocyanates

Abstract

Thiocyanation of ο-, m-, and p-fluoroaniline by the Kaufmann method respectively afforded 3-fluoro-4-aminophenylthiocyanate, 2-fluoro-4-aminophenyl thiocyanate, and 2-amino-6-fluorobenzothiazole. Formylation, acetylation, and benzoylation of these amine compounds were carried out. The four kinds of monofluorinated derivatives, the aniline-type 3-fluoro-4-aminophenylthiocyanate and 2-fluoro-4-aminophenylthiocyanate, and the acetanilide-type 3-fluoro-4-acetaminophenylthiocyanate and 2-fluoro-4-acetaminophenylthiocyanate, all showed marked antifungal action against Trichophyton interdigitale out of four kinds of microorganisms tested. The two kinds of aniline-type 3-fluoro- and 2-fluoro-4-aminophenylthiocyanates had marked antimicrobial activity against Candida albicans.