Synthesis, structural characterization and thromboxane A receptor antagonistic activity of 3-substituted 2-[(arylsulfonyl)imino]-2,3- dihydrothiazolyl derivatives

F. Lacan, M. Varache-Lembège, J. Vercauteren, J.-M. Léger, B. Masereel, J.-M. Dogné, A. Nuhrich

Research output: Contribution to journalArticlepeer-review

Abstract

A series of new 2-[(arylsulfonyl)imino]-2,3-dihydrothiazolyl derivatives substituted on the heterocyclic N by a phenoxyacetic moiety was prepared according to a Hantzsch's synthesis between N, N'-disubstituted thioureas and chloroacetaldehyde. The regiochemistry of the cyclocondensation reaction was established by high resolution NMR methods. Potential thromboxane A/prostaglandin H (TxA/PGH) receptor antagonism was evaluated using human platelet aggregation assays and radioligand binding studies. The results showed that the affinity for the TxA/PGH receptor was strongly dependent on the position of the oxyacetic acid side chain. On the basis of the X-ray crystal analysis of compound 9f, a molecular modelling was undertaken on compounds 3d, 3e, and 3f. Comparison with the 3D structure of sulotroban was discussed.
Original languageEnglish
Pages (from-to)311-328
Number of pages18
JournalEuropean Journal of Medicinal Chemistry
Volume34
Issue number4
DOIs
Publication statusPublished - 1 Apr 1999

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