Document Detail


Optically active antifungal azoles. IV. Synthesis and antifungal activity of (2R,3R)-3-azolyl-2-(substituted phenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanols.
MedLine Citation:
PMID:  7774026     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
(2R,3R)-3-Azolyl-2-(substituted phenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanols (III) were prepared from (2R,3S)-3-methyl-2-(substituted phenyl)-2-(1H-1,2,4-triazol-1-yl)methyloxiranes (21a-f) by a ring-opening reaction with 1H-1,2,3-triazole and 1H-tetrazole and evaluated for antifungal activity against Candida albicans in vitro and in vivo. The optically active oxiranes (21a--f) which serve as the key synthetic intermediates, were synthesized from 1-[(2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxypropanoyl]morpholin e (24) and substituted phenylmagnesium bromide (23) via six steps in a stereocontrolled manner. The 3-(1H-1,2,3,-triazol-1-yl)-(IIIa) and 3-(2H-2-tetrazolyl)-2-butanol (IIId) derivatives showed strong protective effects against candidosis in mice.
Authors:
A Tasaka; N Tamura; Y Matsushita; T Kitazaki; R Hayashi; K Okonogi; K Itoh
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  43     ISSN:  0009-2363     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  1995 Mar 
Date Detail:
Created Date:  1995-07-07     Completed Date:  1995-07-07     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  JAPAN    
Other Details:
Languages:  eng     Pagination:  432-40     Citation Subset:  IM    
Affiliation:
Pharmaceutical Research Laboratories III, Takeda Chemical Industries, Ltd., Osaka, Japan.
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MeSH Terms
Descriptor/Qualifier:
Animals
Antifungal Agents / chemical synthesis*,  pharmacology*
Azoles / chemical synthesis*,  pharmacology*
Butanols / chemical synthesis*,  pharmacology*
Candida albicans / drug effects
Candidiasis / drug therapy
Chemistry, Physical
Magnetic Resonance Spectroscopy
Mice
Mice, Inbred Strains
Microbial Sensitivity Tests
Molecular Structure
Physicochemical Phenomena
Stereoisomerism
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/Antifungal Agents; 0/Azoles; 0/Butanols

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