Collect. Czech. Chem. Commun.
1992, 57, 1103-1110
https://doi.org/10.1135/cccc19921103
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
Abstract
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.
