Ceskoslovenska Akademie Ved

Jirina Slaninova

Tomislav Barth

Michal Lebl

Karel Jost

Alena Machova

Linda Servitova

Hans Vilhardt

Zdenko Prochazka

Jana Skopkova

Miroslava Zertova

Ivo Blaha

Jiri Velek

Lenka Maletinska

Analogues of 8-D-homoarginine vasopressin were prepared with the general formula ##STR1## where X is L-O-methyltyrosine, L-p-ethylphenylalanine, D-p-ethylphenylalanine, L-p-methylphenylalanine or D-methylphenylalanine and R is cysteine or .beta.-mercaptopropionic acid. These vasopressin analogues exhibited an increased affinity to uterus receptors for oxytocin, where they acted as ocytocin antagonists. Moreover, the analogues of deamino vasopressin have a significantly reduced antidiuretic activity in comparison with [8-D-arginine]vasopressin.

Analogues of 8-D-homoarginine vasopressin

Analogs of neurohypophysial hormones with inhibition properties are described. The hormones are of the formula ##STR1## wherein in all chiral amino acids are of the L-series and the aromatic amino acid in the position 2, indicated with an asterisk, is of the D-series, and where R.sup.1 and R.sup.2 are hydrogen or a methyl group, R.sup.3 is hydrogen, an amino group, or a triglycylamine grouping, R.sup.4 is hydrogen, a methyl, ethyl or ethoxy group, R.sup.5 is S--CH.sub.2 or S--S group, X.sup.1 is a residue of isoleucine or phenylalanine, X.sup.2 is a residue of leucine or lysine, and X.sup.3 is a glycinamide residue or a hydroxyl group. These compounds exhibit inhibition effects towards the uterotonic and pressor activity of natural hormones. The common structural feature of all these analogues is the presence of an aromatic hydrophobic D-amino acid in the position 2.

Analogs of neurohypophysial hormones

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