Document Detail


Retinoic acid metabolism inhibition by 3-azolylmethyl-1H-indoles and 2, 3 or 5-(alpha-azolylbenzyl)-1H-indoles.
MedLine Citation:
PMID:  12943199     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Among a library of 70 azoles, 8 indole derivatives substituted in the 2-, 3- or 5- position with an azolylmethyl or alpha-azolylbenzyl chain were evaluated for retinoic acid (RA) metabolism inhibitory activity. The most active inhibitors identified in this study were 5-bromo-1-ethyl-3-methyl-2-[(phenyl)(1H-1,2,4-triazol-1-yl)methyl]-1H-indole (3) (68.9% inhibition) and 5-bromo-1-ethyl-2-[(4-fluorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-3-methyl-1H-indole (6) (60.4% inhibition). At the same concentration (100 microM) ketoconazole exerted similar inhibitory effect (70% inhibition).
Authors:
Marc Le Borgne; Pascal Marchand; Guillaume Le Baut; Masoud Ahmadi; H John Smith; Paul J Nicholls
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Publication Detail:
Type:  In Vitro; Journal Article    
Journal Detail:
Title:  Journal of enzyme inhibition and medicinal chemistry     Volume:  18     ISSN:  1475-6366     ISO Abbreviation:  J Enzyme Inhib Med Chem     Publication Date:  2003 Apr 
Date Detail:
Created Date:  2003-08-28     Completed Date:  2004-01-30     Revised Date:  2007-03-21    
Medline Journal Info:
Nlm Unique ID:  101150203     Medline TA:  J Enzyme Inhib Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  155-8     Citation Subset:  IM    
Affiliation:
Laboratoires de Chimie Organique et de Chimie Thérapeutique, UPRES EA 1155, Faculté de Pharmacie, 1 rue Gaston Veil, F-44035 Nantes, France. marc.leborgne@sante.univ-nantes.fr
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MeSH Terms
Descriptor/Qualifier:
Animals
Cytochrome P-450 Enzyme System / antagonists & inhibitors
Enzyme Inhibitors / chemistry,  pharmacology*
Hydroxylation
Indoles / chemistry,  pharmacology*
Ketoconazole / pharmacology
Microsomes, Liver / enzymology,  metabolism
Molecular Structure
Rats
Structure-Activity Relationship
Tretinoin / metabolism*
Triazoles / chemistry,  pharmacology*
Chemical
Reg. No./Substance:
0/5-bromo-1-ethyl-2-((4-fluorophenyl)(1H-1,2,4-triazol-1-yl)methyl)-3-methyl-1H-indole; 0/5-bromo-1-ethyl-3-methyl-2-((phenyl)(1H-1,2,4-triazol-1-yl)methyl)-1H-indole; 0/Enzyme Inhibitors; 0/Indoles; 0/Triazoles; 302-79-4/Tretinoin; 65277-42-1/Ketoconazole; 9035-51-2/Cytochrome P-450 Enzyme System

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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