title: Synthesis of arginine-vasopressins, modified in positions 1 and 2, as antagonists of the vasopressor response to the parent hormone.
abstract: 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.
authors.affiliation: Institute of Chemistry, University of Gdańsk, Poland.
authors.forename: B
authors.initials: B
authors.lastname: Lammek
authors.forename: P
authors.initials: P
authors.lastname: Rekowski
authors.forename: G
authors.initials: G
authors.lastname: Kupryszewski
authors.forename: P
authors.initials: P
authors.lastname: Melin
authors.forename: U
authors.initials: U
authors.lastname: Ragnarsson
mesh_terms: D000818:Animals; D001127:Arginine Vasopressin / Q000031:analogs & derivatives* / Q000037:antagonists & inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D001794:Blood Pressure / Q000187:drug effects*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D005260:Female; D051381:Rats; D011919:Rats, Inbred Strains
chemical_list: D001127:Arginine Vasopressin