Collect. Czech. Chem. Commun. 1993, 58, 675-680

Analogs of Arginine-Vasopressin Substituted in Position 2 with L-4-Cl-Phenylalanine or D-Phenylglycine

Malgorzata Czajaa, Ewa Koniecznaa, 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 Praque 6, Czech Republic


Eight new compounds were designed, synthesized and bioassayed as a part of our studies on the structure-activity relationship of arginine-vasopresine (AVP) analogs. Tyrosine in position 2 of AVP, dAVP, [Cpp1]AVP and [Cpp1,Val4]AVP was substituted by L-4-chlorophenylalanine (4-Cl-Phe) or D-phenylglycine [D-Gly(Phe)] and the effect of these changes on agonistic/antagonistic activity in uterotonic and pressor test was followed. All but one of these analogs were found inhibitory in uterotonic test, however in most cases their potency was fairly low. As to the pressor activity the agonistic potency of the 4-Cl-Phe substituted analogs was essentially the same as having 4-F-Phe in position 2. As far as the potency of antagonists is concerned, 4-Cl-Phe peptides showed significantly higher potency than the 4-F-Phe analogs. All compounds containing D-phenylglycine in position 2 were inactive in the pressor test.