Collect. Czech. Chem. Commun. 1992, 57, 1103-1110

The Analogs of 8-D-Homoarginin-vasopressin with O-Substituted Phenylalanine in Position 2: Synthesis and Some Biological Properties

Miroslava Žertová, Zdenko Procházka, Jiřina Slaninová, Tomislav Barth, Pavel Majer and Michal Lebl

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


Solid phase methodology on p-methylbenzhydrylamine resin was used for the synthesis of four analogs of vasopressin with the non coded amino acids, D-homoarginine (in position 8) and o-substituted L- or D-phenylalanine (in position 2). [L-Phe(o-Me)2,D-Har8]vasopressin (I), [D-Phe(o-Me)2,D-Har8]vasopressin (II), [L-Phe(o-Et)2,D-Har8]vasopressin (III) and [D-Phe(o-Et)2,D-Har8]vasopressin (IV) were synthesized. All analogs had very low antidiuretic activity. Analogs I and IV were low pressor inhibitors. All analogs were found to be the uterotonic inhibitors, the most potent on in vitro being [D-Phe(o-Et)2,D-Har8]vasopressin with a pA2 = 8.4.