Synthesis, structural characterization and thromboxane A2 receptor antagonistic activity of 3-substituted 2-[(arylsulfonyl)imino]-2,3-dihydrothiazolyl derivatives
| Autor: | Jean-Michel Léger, A. Nuhrich, Joseph Vercauteren, Martine Varache-Lembège, Jean-Michel Dogné, F. Lacan, Bernard Masereel |
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| Rok vydání: | 1999 |
| Předmět: |
Pharmacology
chemistry.chemical_classification Molecular model Stereochemistry Carboxylic acid Organic Chemistry Regioselectivity General Medicine Chemical synthesis Thromboxane A2 chemistry.chemical_compound chemistry Drug Discovery Moiety Chloroacetaldehyde lipids (amino acids peptides and proteins) Prostaglandin H2 circulatory and respiratory physiology |
| Zdroj: | European Journal of Medicinal Chemistry. 34:311-328 |
| ISSN: | 0223-5234 |
| DOI: | 10.1016/s0223-5234(99)80082-8 |
| Popis: | 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 A2/prostaglandin H2 (TxA2/PGH2) receptor antagonism was evaluated using human platelet aggregation assays and radioligand binding studies. The results showed that the affinity for the TxA2/PGH2 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. |
| Databáze: | OpenAIRE |
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