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Synthesis and some pharmacological properties (4-beta-(2-thienyl)-L-alanine)oxytocin.

Abstract：

:The synthesis and some biological activities of [4-beta-(2-thienyl)-L-alanine]oxytocin are reported. This analogue has been studied in an ongoing exploration of the biological effects of introducing amino acid residues with bulky hydrophobic side chains into the second corner position of the beta turn present in the conformation of the 20-membered ring portion of oxytocin. The analogue was synthesized in stepwise manner by solution techniques utilizing ethylcarbamoyl protection for cysteine side chains. The presence of thienylalanine in position 4 evokes a drastic reduction in both affinity and intrinsic activity; the reduction in intrinsic activity was greater than that found for [Leu4]oxytocin or [Phe4]oxytocin. The analogue possesses 0.51 +/- 0.03 unit/mg of rat uterotonic potency and less than 0.05 unit/mg of rat pressor and rat antidiuretic potency and behaves as a competitive inhibitor of the response to oxytocin in the avian vasodepressor assay with a pA2 value of 7.44 +/- 0.19.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Smith CW,Skala G,Walter R

doi

10.1021/jm00199a022

subject

Has Abstract

pub_date

1978-01-01 00:00:00

pages

115-7

issue

1

eissn

0022-2623

issn

1520-4804

journal_volume

21

pub_type

杂志文章

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