Collect. Czech. Chem. Commun. 1992, 57, 1345-1351

Synthesis and Properties of "Hormonogene" and "Inhibitorogene" Type Oxytocin Analogs

B. C. Pala, Jiřina Slaninováa, Tomislav Bartha, Jerzy Trojnarb and Michal Lebla

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Ferring Pharmaceuticals, S-200 62 Malmö, Sweden


Nα-Glycyl, diglycyl and triglycyl [2-D and [2-L-p-ethylphenylalanine]oxytocin analogs were synthesized by the solid phase technology utilizing racemic p-ethylphenylalanine. Analogs containing this amino acid of D-configuration were shown to be weak uterotonic antagonists both in vitro and in vivo tests; the compound containing triglycyl residue in position 1 was shown to have prolonged time course of inhibitory action. Analogs containing the L-amino acid were shown to be inhibitors of uterotonic activity of oxytocin in vitro, but uterotonic agonists with prolonged effect in vivo.