Collect. Czech. Chem. Commun. 1993, 58, 2994-2999

Synthesis and Some Pharmacological Properties of Six New Analogs of Arginine-Vasopressin Substituted in Position 2 with β-Thienylalanine or Prolonged on the N-Terminus with 1-Adamantaneacetic Acid

Ewa Koniecznaa, Malgorzata Czajaa, Bernard Lammeka, Jiřina Slaninováb and Tomislav Barthb

a Department of Chemistry, University of Gdansk, 80-952 Gdańsk, Poland
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


Six new analogs of arginine-vasopressin, four of them substituted in position 2 with β-thienylalanine and two prolonged on the n-terminus by acylation with 1-adamantaneacetic acid, were synthesized on chloromethylated resin using Boc strategy and DCC or DCC-HOBt to form peptide bond. The activity of the analogs was fairly low, however, one of the peptides, namely [Cpp1, Thi2, Val4]AVP, showed selectivity in antiuterotonic, antipressor and anti-antidiuretic effects.