Design, synthesis and biological evaluation of a sulfonylcyanoguanidine as thromboxane A2 receptor antagonist and thromboxane synthase inhibitor-Reference-Cited by-同舟云学术

Design, synthesis and biological evaluation of a sulfonylcyanoguanidine as thromboxane A2 receptor antagonist and thromboxane synthase inhibitor

Published:2001-05 Issue:5 Volume:53 Page:669-680
ISSN:0022-3573
Container-title:Journal of Pharmacy and Pharmacology
language:en
Short-container-title:

Author:

Dogné Jean-Michel¹,Wouters Johan²,Rolin Stéphanie³,Michaux Catherine²,Pochet Lionel³,Durant François²,Delarge Jacques¹,Masereel Bernard³

Affiliation:

1. Laboratory of Medicinal Chemistry, University of Liège, 4000 Liège, Belgium

2. Laboratory of Molecular Structures, University of Namur, 61 rue de Bruxelles, 5000 Namur, Belgium

3. Department of Pharmacy, University of Namur, 61 rue de Bruxelles, 5000 Namur, Belgium

Abstract

Abstract The synthesis and the structure of N-isopropyl-N′-[2-(3′-methylphenylamino)-5-nitrobenzenesulfonyl] urea (14) was drawn from two thromboxane A2 receptor antagonists structurally related to torasemide. Compound 14 showed an IC50 value of 22 nm for the thromboxane A2 (TXA2) receptor of human washed platelets. Compound 14 prevented platelet aggregation induced by arachidonic acid (0.6 mm) and U-46619 (1 μm) with an IC50 value of 0.45 and 0.15 μm, respectively. Moreover, 14 relaxed the rat isolated aorta and guinea-pig trachea precontracted by U-46619, a TXA2 agonist. Its efficacy (IC50) was 20.4 and 5.47 nm, respectively. Finally, 14 (1 μm) completely inhibited TXA2 synthase of human platelets. The pKa value and the crystallographic data of 14 were determined and used to propose an interaction model between the TXA2 antagonists related to torasemide and their receptor.

Publisher

Oxford University Press (OUP)

Subject

Pharmaceutical Science,Pharmacology

Link

http://academic.oup.com/jpp/article-pdf/53/5/669/36783518/0022357011775992.pdf

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