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Titolo:
5-(SULFONYL)OXY-TRYPTAMINES AND ETHYLAMINO SIDE-CHAIN RESTRICTED DERIVATIVES - STRUCTURE-AFFINITY RELATIONSHIPS FOR H5-HT1B AND H5-HT1D RECEPTORS
Autore:
BARF T; WIKSTROM H; PAUWELS PJ; PALMIER C; TARDIF S; LUNDMARK M; SUNDELL S;
Indirizzi:
PHARMACIA & UPJOHN INC,DEPT CHEM,RAPSGATAN 7 S-75182 UPPSALA SWEDEN UNIV GRONINGEN,CTR PHARM,DEPT MED CHEM NL-9713 AV GRONINGEN NETHERLANDS CTR RECH PIERRE FABRE F-81106 CASTRES FRANCE GOTHENBURG UNIV,DEPT BIOCHEM MED S-41390 GOTHENBURG SWEDEN
Titolo Testata:
Bioorganic & medicinal chemistry
fascicolo: 9, volume: 6, anno: 1998,
pagine: 1469 - 1479
SICI:
0968-0896(1998)6:9<1469:5AESRD>2.0.ZU;2-V
Fonte:
ISI
Lingua:
ENG
Soggetto:
5-HT1D RECEPTOR; SEROTONERGIC ACTIVITY; POTENT AGONISTS; BRAIN MEMBRANES; PHARMACOLOGY; BINDING; SITES; AUTORECEPTORS; SUMATRIPTAN; SUBFAMILY;
Keywords:
SEROTONIN; 5-HT; SULFONATE; H5-HT1B; H5-HT1D;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
37
Recensione:
Indirizzi per estratti:
Citazione:
T. Barf et al., "5-(SULFONYL)OXY-TRYPTAMINES AND ETHYLAMINO SIDE-CHAIN RESTRICTED DERIVATIVES - STRUCTURE-AFFINITY RELATIONSHIPS FOR H5-HT1B AND H5-HT1D RECEPTORS", Bioorganic & medicinal chemistry, 6(9), 1998, pp. 1469-1479

Abstract

A number of sulfonic acid ester derivatives of serotonin (5-hydroxytryptamine; 5-HT; 1) were prepared and their affinities are compared to that of the reference compound 5-[[(trifluoromethyl)sulfonyl]oxy]-tryptamine (8b). The structure-affinity relationship (SAFIR) is discussed in terms of in vitro binding for cloned human h5-HT1A, h5-HT1B and h5-HT1D receptors. All tryptamine derivatives exhibited the best affinities for h5-HT1D receptors but still, these were comparatively lower than that of compound 8b. 5-Tosylated tryptamine 11b (K-i = 6 nM) and thesulfamate derivatives 13b and 14b (K-i = 7 and 11 nM, respectively) were found to have the highest affinities for the h5-HT1D receptor. Other tryptamine derivatives displayed moderate binding for h5-HT1A and h5-HT1B receptors, along with Ki values ranging from 14-20 nM for the h5-HT1D sites. In addition, the syntheses of two alkylamino side chain restricted derivatives are described. romethyl)sulfonyl]oxy]-1,2,3,4-tetrahydrocarbazole 21, as well as uoromethyl)sulfonyl]oxy]-1H-indol-3-yl]piperidines 24 and 25, induced a shift in selectivity in favor of the h5-HT1B receptor. The relatively longer distance between the basic amine and a hydrogen-bond accepting oxygen in 21, 24 and 25 as compared to the non-restricted tryptamines, is likely responsible for this observation. (C) 1998 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 08/04/20 alle ore 09:03:15