THE 1-NAPHTHYLALANINE AND 2-NAPHTHYLALANINE ANALOGS OF OXYTOCIN AND VASOPRESSIN

Solid phase technique on p-methylbenzhydrylamine resin was used for th e synthesis of four analogs of oxytocin and four analogs of vasopressi n with the non-coded amino acids L- or D- and 1- or 2-naphthyl-alanine and D-homoarginine. [L-1-Nal(2)]oxytocin, [D-1-Nal(2)]oxytocin, [L-2- Nal(2)]oxytocin, [D-2-Nal(2)]oxytocin, [L-1-Nal(2), D-Har(8)]vasopress in, [D-1-Nal(2), D-Har(8)]vasopressin, [L-2-Nal(2), D-Har(8)]vasopress in and [D-2-Nal(2), D-Har(8)]vasopressin were synthesized. All eight a nalogs were found to be uterotonic inhibitors in vitro and in vivo. An alogs with 2-naphthylalanine are stronger inhibitors, particularly in the vasopressin series than the analogs with 1-naphthylalanine. Analog s with 1-naphthylalanine have no activity in the presser test, analogs with 2-naphthylalanine are weak presser inhibitors.