Syntheses and antifungal activity of dl-griseofulvin and its congeners. II

Yasuo Takeuchi, Hideo Tomozane, Keiji Misumi, Kuniko Yata, Teruyuki Kawata, Yoshiko Niino, Masatoshi Yamato, Takashi Harayama

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7 Citations (Scopus)

Abstract

Griseofulvin derivatives, dl-6'-demethyl-6'-ethylgriseofulvin (dl-5) and dl-6'-demethyl-6'-phenylgriseofulvin (dl-6) were prepared by application of a synthetic method developed by us. Antifungal activity of these derivatives decreased in the order of dl-griseofulvin (dl-1) > dl-5 >> dl-6 (inactive). The reaction of these derivatives with ethanethiol gave two types of compounds, 2'-(ethylthio)griseofulvin (15) and 4'-(ethylthio)isogriseofulvin (16). The relationship between the ratios of isolated yield of 15 and 16 and antifungal the activity of griseofulvin derivatives is discussed.

Original languageEnglish
Pages (from-to)327-332
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume45
Issue number2
Publication statusPublished - 1997

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Keywords

  • antifungal activity
  • epigriseofulvin
  • griseofulvin derivative
  • thiogriseofulvin
  • thiol

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

Cite this

Takeuchi, Y., Tomozane, H., Misumi, K., Yata, K., Kawata, T., Niino, Y., Yamato, M., & Harayama, T. (1997). Syntheses and antifungal activity of dl-griseofulvin and its congeners. II. Chemical and Pharmaceutical Bulletin, 45(2), 327-332.