Document Detail

Synthesis of arginine-vasopressins, modified in positions 1 and 2, as antagonists of the vasopressor response to the parent hormone.
MedLine Citation:
PMID:  3346876     Owner:  NLM     Status:  MEDLINE    
In an attempt to determine some of the structural features in position 1 that account for antivasopressor activity, eight new 1-(beta, beta-dialkyl-substituted) analogues of 1-(3-mercaptopropanoic acid)-8-arginine-vasopressin and 1-(3-mercaptopropanoic acid)-2-O-methyltyrosine-8-arginine-vasopressin have been designed and synthesized. The protected precursors required for these peptides were obtained by a combination of solid-phase and solutions methods. Some of the reported analogues, namely 1-(1-mercapto-4-methylcyclohexaneacetic acid)-8-arginine-vasopressin, 1-(1-mercapto-4-methylcyclohexaneacetic acid)-2-O-methyltryosine-8-arginine-vasopressin, 1-(4-tert-butyl-1-mercaptocyclohexaneacetic acid)-2-O-methyltyrosine-8-arginine- vasopressin, 1-(1-mercapto-4-phenylcyclohexaneacetic acid)-8-arginine-vasopressin and 1-(1-mercapto-4-phenylcyclohexaneacetic acid)-2-O-methyltyrosine-8-arginine- vasopressin, are among the most potent and selective antagonists of the vasopressor response to arginine-vasopressin reported to date.
B Lammek; P Rekowski; G Kupryszewski; P Melin; U Ragnarsson
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  31     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1988 Mar 
Date Detail:
Created Date:  1988-04-11     Completed Date:  1988-04-11     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  603-6     Citation Subset:  IM    
Institute of Chemistry, University of Gdańsk, Poland.
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MeSH Terms
Arginine Vasopressin / analogs & derivatives*,  antagonists & inhibitors,  chemical synthesis,  pharmacology
Blood Pressure / drug effects*
Chemistry, Physical
Physicochemical Phenomena
Rats, Inbred Strains
Reg. No./Substance:
113-79-1/Arginine Vasopressin

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

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