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

Research output: Contribution to journalArticle

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

Fingerprint

Griseofulvin
Derivatives

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., ... Harayama, T. (1997). Syntheses and antifungal activity of dl-griseofulvin and its congeners. II. Chemical and Pharmaceutical Bulletin, 45(2), 327-332.

Syntheses and antifungal activity of dl-griseofulvin and its congeners. II. / Takeuchi, Yasuo; Tomozane, Hideo; Misumi, Keiji; Yata, Kuniko; Kawata, Teruyuki; Niino, Yoshiko; Yamato, Masatoshi; Harayama, Takashi.

In: Chemical and Pharmaceutical Bulletin, Vol. 45, No. 2, 1997, p. 327-332.

Research output: Contribution to journalArticle

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, vol. 45, no. 2, pp. 327-332.
Takeuchi Y, Tomozane H, Misumi K, Yata K, Kawata T, Niino Y et al. Syntheses and antifungal activity of dl-griseofulvin and its congeners. II. Chemical and Pharmaceutical Bulletin. 1997;45(2):327-332.
Takeuchi, Yasuo ; Tomozane, Hideo ; Misumi, Keiji ; Yata, Kuniko ; Kawata, Teruyuki ; Niino, Yoshiko ; Yamato, Masatoshi ; Harayama, Takashi. / Syntheses and antifungal activity of dl-griseofulvin and its congeners. II. In: Chemical and Pharmaceutical Bulletin. 1997 ; Vol. 45, No. 2. pp. 327-332.
@article{c02c3fef55cf471a80c6bad8a1a35a65,
title = "Syntheses and antifungal activity of dl-griseofulvin and its congeners. II",
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.",
keywords = "antifungal activity, epigriseofulvin, griseofulvin derivative, thiogriseofulvin, thiol",
author = "Yasuo Takeuchi and Hideo Tomozane and Keiji Misumi and Kuniko Yata and Teruyuki Kawata and Yoshiko Niino and Masatoshi Yamato and Takashi Harayama",
year = "1997",
language = "English",
volume = "45",
pages = "327--332",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "Pharmaceutical Society of Japan",
number = "2",

}

TY - JOUR

T1 - Syntheses and antifungal activity of dl-griseofulvin and its congeners. II

AU - Takeuchi, Yasuo

AU - Tomozane, Hideo

AU - Misumi, Keiji

AU - Yata, Kuniko

AU - Kawata, Teruyuki

AU - Niino, Yoshiko

AU - Yamato, Masatoshi

AU - Harayama, Takashi

PY - 1997

Y1 - 1997

N2 - 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.

AB - 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.

KW - antifungal activity

KW - epigriseofulvin

KW - griseofulvin derivative

KW - thiogriseofulvin

KW - thiol

UR - http://www.scopus.com/inward/record.url?scp=0030997236&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030997236&partnerID=8YFLogxK

M3 - Article

C2 - 9118447

AN - SCOPUS:0030997236

VL - 45

SP - 327

EP - 332

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 2

ER -