Collect. Czech. Chem. Commun. 1990, 55, 3000-3007

The analogs of 8-D-homoarginine-vasopressin with p-substituted phenylalanine in position 2; Synthesis and some biological properties

Miroslava Žertová, Zdenko Procházka, Ivo Bláha, Tomislav Barth, Jiřina Slaninová, Lenka Maletínská and Michal Lebl

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Solid phase methodology on benzhydrylamine resin was used for the synthesis of five analogs of vasopressin with non-coded amino acid, D-homoarginine, in position 8 and p-substituted D or L phenylalanine in position 2. Besides the mother analog, [D-Har8]vasopressin (I), [L-Phe(Me)2, D-Har8]vasopressin (II), [D-Phe(Me)2, D-Har8]vasopressin (III), [L-Phe(Et)2, D-Har8]vasopressin (IV), [D-Phe(Et)2, D-Har8]vasopressin (V) were synthesized. All analogs have very low antidiuretic and pressor activities. Analogs containing p-ethylphenylalanine of both D and L configuration are pressor inhibitors. All analogs substituted in position 2 were found to be uterotonic inhibitors, the most potent being [D-Phe(Et)2, D-Har8]vasopressin (V) with pA2 8.15.