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

doi:10.1248/cpb.45.327

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 journal › Article › peer-review

2 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 language	English
Pages (from-to)	327-332
Number of pages	6
Journal	Chemical and Pharmaceutical Bulletin
Volume	45
Issue number	2
DOIs	https://doi.org/10.1248/cpb.45.327
Publication status	Published - Feb 1997

Keywords

antifungal activity
epigriseofulvin
griseofulvin derivative
thiogriseofulvin
thiol

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.45.327

Cite this

@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",

month = feb,

doi = "10.1248/cpb.45.327",

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 - 1997/2

Y1 - 1997/2

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

U2 - 10.1248/cpb.45.327

DO - 10.1248/cpb.45.327

M3 - Article

C2 - 9118447

AN - SCOPUS:0030997236

SN - 0009-2363

VL - 45

SP - 327

EP - 332

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 2

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this