Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668

Triazole analogues which contained alkylthio or alkylsulfonyl groups where synthesized as derivatives of antifungal SM-8668 and estimated for their in vitro and in vivo activity. Derivatives having pentylthio, heptylthio or nonylthio groups showed excellent efficacy against both candidiasis and aspe...

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Veröffentlicht in:Bioorganic & medicinal chemistry 1996-02, Vol.4 (2), p.263-273
Hauptverfasser: Miyauchi, Hiroshi, Kozuki, Koichi, Tanio, Tomoharu, Ohashi, Naohito
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container_issue 2
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container_title Bioorganic & medicinal chemistry
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creator Miyauchi, Hiroshi
Kozuki, Koichi
Tanio, Tomoharu
Ohashi, Naohito
description Triazole analogues which contained alkylthio or alkylsulfonyl groups where synthesized as derivatives of antifungal SM-8668 and estimated for their in vitro and in vivo activity. Derivatives having pentylthio, heptylthio or nonylthio groups showed excellent efficacy against both candidiasis and aspergillosis. Introduction of a hydrophilic group at the end of their alkyl chain made their activity stronger. Especially, 5-hydroxypentylthio and 7-hydroxyheptylthio derivatives showed the strongest antifungal activity. Alkyl derivatives of sulfur-containing triazoles 1 were synthesized and estimated for their antifungal activities. Some of the compounds showed potent activities against both candidiasis and aspergillosis. The induction of hydroxyl group at the end of their alkyl chain made their activities stronger.
doi_str_mv 10.1016/0968-0896(95)00180-8
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source MEDLINE; Elsevier ScienceDirect Journals
subjects Alkylation
Animals
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Antifungal Agents - therapeutic use
Aspergillosis - drug therapy
Candidiasis - drug therapy
Disease Models, Animal
Magnetic Resonance Spectroscopy
Male
Mice
Structure-Activity Relationship
Sulfur - chemistry
Triazoles - chemistry
Triazoles - metabolism
title Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668
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