Strong uterotonic inhibitors – analogs of 1-deamino-8-D-homoarginine-vasopressin with p-substituted phenylalanine in position 2

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Title:Strong uterotonic inhibitors – analogs of 1-deamino-8-D-homoarginine-vasopressin with p-substituted phenylalanine in position 2
Creators:
Žertová, Miroslava
Procházka, Zdenko
Barth, Tomislav
Slaninová, Jiřina
Škopková, Jana
Bláha, Ivo
Lebl, Michal
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 8, pp. 1761-1767

Abstract

Solid phase methodology on benzhydrylamine or <i>p</i>-methylbenzhydrylamine resin was used for the synthesis of five analogs of deamino-vasopressin with non-coded amino acids. D-homoarginine, in position 8 and <i>p</i>-substituted D- or L-phenylalanine in position 2. Besides the mother analog, [Mpr<sup>1</sup>, D-Har<sup>8</sup>]vasopressin (<i>I</i>), [Mpr<sup>1</sup>, L-Phe(<i>p</i>-Me)<sup>2</sup>, D-Har<sup>8</sup>]vasopressin (<i>II</i>), [Mpr<sup>1</sup>, D-Phe(<i>p</i>-Me)<sup>2</sup>,D-Har<sup>8</sup>]vasopressin (<i>III</i>), [Mpr<sup>1</sup>, L-Phe(<i>p</i>-Et)<sup>2</sup>, D-Har<sup>8</sup>]vasopressin (<i>IV</i>) and [Mpr<sup>1</sup>, D-Phe(<i>p</i>-Et)<sup>2</sup>, D-Har<sup>8</sup>]vasopressin (<i>V</i>) were synthesized. All analogs have very low antidiuretic and pressor activities. Analogs containing <i>p</i>-methylphenylalanine of L-configuration and <i>p</i>-ethylphenylalanine of both D- and L-configuration are pressor inhibitors. All analogs substituted in position 2 were found to act as the uterotonic inhibitors, the most potent being [Mpr<sup>1</sup>, D-Phe(<i>p</i>-Et)<sup>2</sup>, D-Har<sup>8</sup>]vasopressin (<i>V</i>) with p<i>A</i><sub>2</sub> = 8.30.

Title:Strong uterotonic inhibitors – analogs of 1-deamino-8-D-homoarginine-vasopressin with p-substituted phenylalanine in position 2
Creators:
Žertová, Miroslava
Procházka, Zdenko
Barth, Tomislav
Slaninová, Jiřina
Škopková, Jana
Bláha, Ivo
Lebl, Michal
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:8
Page Range:pp. 1761-1767
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19911761UNSPECIFIED
ID Code:5103
Item Type:Article
Deposited On:22 Feb 2010 11:30
Last Modified:22 Feb 2010 10:30

Citation

Žertová, Miroslava; Procházka, Zdenko; Barth, Tomislav; Slaninová, Jiřina; Škopková, Jana; Bláha, Ivo; Lebl, Michal (1991) Strong uterotonic inhibitors – analogs of 1-deamino-8-D-homoarginine-vasopressin with p-substituted phenylalanine in position 2. Collection of Czechoslovak Chemical Communications, 56 (8). pp. 1761-1767. ISSN 0010-0765

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