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Synthesis and pharmacological properties of a close analogue of an antithrombotic pentasaccharide (SR 90107A/ORG 31540).

Abstract：

:The synthetic pentasaccharide (1) corresponding to the heparin sequence which binds to, and activates, antithrombin III (AT III) is a potent antithrombotic compound in several animal models of venous thrombosis. We describe here the preparation and the pharmacological properties of 34, an analogue of oligosaccharide 1 with the latter's N-sulfates being replaced by sulfate esters and hydroxyl groups being methylated. These structural modifications allow a simpler and more efficient synthesis of such anionic oligosaccharides. Affinity for human AT III, anti-factor Xa activity, ability to inhibit thrombin generation, antithrombotic activity in a rat model of venous thrombosis, and elimination half-life in the rat have been determined for 1 and 34. Surprisingly, introduction of O-sulfates in place of N-sulfates, and methylation of hydroxyl groups, contributes to reinforce the binding to AT III, resulting in an improved pharmacological profile.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Petitou M,Duchaussoy P,Jaurand G,Gourvenec F,Lederman I,Strassel JM,Bârzu T,Crépon B,Hérault JP,Lormeau JC,Bernat A,Herbert JM

doi

10.1021/jm960726z

subject

Has Abstract

pub_date

1997-05-23 00:00:00

pages

1600-7

issue

11

eissn

0022-2623

issn

1520-4804

pii

jm960726z

journal_volume

40

pub_type

杂志文章

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