The Deamino-Carba Analogs of Vasotocin. Synthesis and Some Biological Properties

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Title:The Deamino-Carba Analogs of Vasotocin. Synthesis and Some Biological Properties
Creators:
Procházka, Zdenko
Slaninová, Jiřina
Melin, Per
Aurell, Carl-Johan
Lebl, Michal
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 2, pp. 421-428

Abstract

<p>Solid phase methodology on benzhydrylamine resin with linkage agent and Fmoc technique was used for the synthesis of two analogs of deamino carba-1 and carba-6 oxytocin with phenylalanine in position 2 and with ornithine in position 8. The following analogs were prepared: [Phe<sup>2</sup>,Orn<sup>8</sup>]deamino-carba-1-oxytocin (<i>I</i>) and [Phe<sup>2</sup>,Orn<sup>8</sup>]deamino-carba-6-oxytocin (<i>II</i>). Moreover, analogs with δ-amino group of ornithine protected by benzyloxycarbonyl group and its corresponding sulfoxides were isolated and tested. Both deprotected analogs were found to have high uterotonic activity in vivo, and moderate pressor and antidiuretic agonistic activity. Surprisingly, in uterotonic test they are only partial agonists. The analogs with protected ornithine have preserved high uterotonic <i>in vivo</i> activity in contrary to the pressor activity that was strongly decreased.

Title:The Deamino-Carba Analogs of Vasotocin. Synthesis and Some Biological Properties
Creators:
Procházka, Zdenko
Slaninová, Jiřina
Melin, Per
Aurell, Carl-Johan
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:59
Number:2
Page Range:pp. 421-428
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19940421UNSPECIFIED
ID Code:458
Item Type:Article
Deposited On:06 Feb 2009 17:01
Last Modified:06 Feb 2009 16:01

Citation

Procházka, Zdenko; Slaninová, Jiřina; Melin, Per; Aurell, Carl-Johan; Lebl, Michal (1994) The Deamino-Carba Analogs of Vasotocin. Synthesis and Some Biological Properties. Collection of Czechoslovak Chemical Communications, 59 (2). pp. 421-428. ISSN 0010-0765

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