Document Detail


Variations of acidic functions at position 2 and substituents at positions 4, 5 and 6 of the indole moiety and their effect on NMDA-glycine site affinity.
MedLine Citation:
PMID:  14575932     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The synthetic procedures to obtain indole derivatives with different acidic functions at position 2 of the indole are reported. The synthesised and tested derivatives comprise 5-tetrazolyl, 1,3,4-oxadiazol-5-yl-2-one, and indole-2-carboxylic acid amides with 5-aminotetrazole, methanesulphonamide and trifluoromethanesulphonamide moieties. The binding affinity was evaluated using [3H]MDL 105,519 and pig cortical brain membranes. In general, compounds with acidic functions different from a carboxylic acid moiety are less potent than indole-2-carboxylic acid derivatives. Also, the 4,6-dichloro substitution pattern was compared to 5-tert-butyl derivatives and compounds not substituted in the benzene moiety of the indole, indicating that the affinity increases from 5-tert-butyl over unsubstituted to 4,6-dichloro substituted derivatives.
Authors:
Michaela Jansen; Gerd Dannhardt
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  European journal of medicinal chemistry     Volume:  38     ISSN:  0223-5234     ISO Abbreviation:  Eur J Med Chem     Publication Date:  2003 Oct 
Date Detail:
Created Date:  2003-10-24     Completed Date:  2004-07-08     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0420510     Medline TA:  Eur J Med Chem     Country:  France    
Other Details:
Languages:  eng     Pagination:  855-65     Citation Subset:  IM    
Affiliation:
Department of Medicinal and Pharmaceutical Chemistry, Institute of Pharmacy, Johannes Gutenberg-University, Staudinger Weg 5, 55099 Mainz, Germany.
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MeSH Terms
Descriptor/Qualifier:
Animals
Binding Sites
Cell Membrane / chemistry
Cerebral Cortex / chemistry
Glycine
Indoles / chemical synthesis*,  chemistry,  pharmacology*
Inhibitory Concentration 50
Models, Molecular
Radioligand Assay
Receptors, N-Methyl-D-Aspartate / antagonists & inhibitors,  chemistry*
Structure-Activity Relationship
Swine
Chemical
Reg. No./Substance:
0/Indoles; 0/MDL 105519; 0/Receptors, N-Methyl-D-Aspartate; 56-40-6/Glycine

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


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