Collect. Czech. Chem. Commun. 1991, 56, 933-938

Synthesis and biological activity of four vasopressin analogues substituted in position 2 by p-fluorophenylalanine

Bernard Lammeka, Izabela Derdowskaa, Gotfryd Kupryszewskia, Jiřina Slaninováb and Tomislav Barthb

a Institute of Chemistry, University of Gdańsk, 80-952 Gdansk, Poland
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia


Tyrosine in position 2 of AVP, dAVP, [Cpp1]AVP and [Cpp1, Val4]AVP was substituted by p-fluorophenylalanine and an effect of this change on agonistic/antagonistic activity in uterotonic, pressor or anti-antidiuretic test was followed. All the prepared analogues were found inhibitory in uterotonic test, however the inhibitory potency was rather low. As far as the pressor activity is concerned, the agonistic potency was slightly decreased (2-4 times), in comparison with the strong decrease of the inhibitory potency.