Collect. Czech. Chem. Commun. 1991, 56, 491-498

Synthesis of four new V1 antagonists of arginine-vasopressin (AVP) containing new thioacids at position 1 and their vasoconstrictor activity towards isolated mesenteric arterial vessels of rats

Bernard Lammeka, Izabela Derdowskaa, Tomasz M. Wierzbab and Witold Juzwab

a Institute of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland
b Department of Physiology, Medical Academy of Gdańsk, Dębinki 1, 80-211 Gdańsk, Poland


In an attempt to determine some of the structural features in position 1 that account for V1 antagonism, four new analogues of arginine-vasopressin were synthesized and the effect of the modifications on the vasoconstrictor activity was checked using isolated mesenteric arterial vessels of rats. The protected precursors required for these analogues were synthesized by a solid phase method of peptide synthesis. One of the reported analogues, namely [1-(4-mercapto-4-tetrahydrothiopyraneacetic acid)., 2-O-methyltyrosine, 8-arginine]vasopressin appears to be a potent competitive antagonist of the vasoconstrictor effect by AVP.