Synthesis and some pharmacological properties of oxytocin and vasopressin analogs with sarcosine or N-methyl-L-alanine in position 7

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Abstract
Eight analogs of oxytocin and arginine-vasopressin were synthesized, in which the proline residue in position 7 was replaced by either sarcosine or N-methylalanine; some of the pharmacological properties of these analogs were evaluated. In peptides containing a .beta.-mercaptopropionic acid residue in position 1, the additivity of the effects of delection of the amino group in position 1 and of the above-noted replacements in position 7 on biological properties of these analogs was ascertained. All of the analogs were potent in either [rat] antidiuretic or uterine activity and also selective in action. From the point of view of pharmacological properties, substitution of sarcosine in position 7 of oxytocin gave analogs with higher oxytocic and milk-ejecting activities than did the substitution of N-methylalanine. The opposite structure-activity relationship was observed with arginine-vasopressin, where the N-methylalanine-containing analogs were more potent than the sarcosine-containing analogs with respect to pressor activity and also, if not deaminated, with respect to pressor activity and also, if not deaminated, with respect to antidiuretic activity.

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