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Titolo:
FLEXIBLE 1-[(2-AMINOETHOXY)ALKYL]-3-AR(O)YL(THIO)UREAS AS NOVEL ACETYLCHOLINESTERASE INHIBITORS - SYNTHESIS AND BIOCHEMICAL EVALUATION
Autore:
VIDALUC JL; CALMEL F; BIGG DCH; CARILLA E; BRILEY M;
Indirizzi:
CTR RECH PIERRE FABRE,DIV MED CHEM,17 AVE JEAN MOULIN F-81106 CASTRESFRANCE CTR RECH PIERRE FABRE,DEPT NEUROBIOL F-81106 CASTRES FRANCE
Titolo Testata:
Journal of medicinal chemistry
fascicolo: 15, volume: 38, anno: 1995,
pagine: 2969 - 2973
SICI:
0022-2623(1995)38:15<2969:F1ANA>2.0.ZU;2-D
Fonte:
ISI
Lingua:
ENG
Soggetto:
CENTRAL CHOLINERGIC AGENTS; ALZHEIMERS-DISEASE; ANTIACETYLCHOLINESTERASE ACTIVITY; PROTEASE INHIBITORS; AMYLOID PROTEIN; HUPERZINE-A; CHOLINESTERASES; BRAIN; FORM; DERIVATIVES;
Tipo documento:
Note
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
61
Recensione:
Indirizzi per estratti:
Citazione:
J.L. Vidaluc et al., "FLEXIBLE 1-[(2-AMINOETHOXY)ALKYL]-3-AR(O)YL(THIO)UREAS AS NOVEL ACETYLCHOLINESTERASE INHIBITORS - SYNTHESIS AND BIOCHEMICAL EVALUATION", Journal of medicinal chemistry, 38(15), 1995, pp. 2969-2973

Abstract

A series of flexible 1-(2-aminoethoxy)-3-ar(o)yl(thio)ureas was synthesized and assessed for antiacetylcholinesterase activity. This serieswas designed in order to optimize the spacer length linking the two pharmacophoric moieties, i.e., the basic nitrogen and the ar(o)yl(thio)urea unit, and to test compounds with greater conformational flexibility. Thus, the replacement of the previously described spacer, 4-piperidinylethyl, by a linear ethoxyethyl chain gave compounds of slightly comparable potency, providing that they were correctly substituted. Theresults show that this new flexible spacer is compatible with high inhibitory activities. The optimal chain length corresponds to five methylene groups, allowing an efficient interaction between the two pharmacophoric units and the two reported hypothetical enzyme hydrophobic binding sites. Moreover, the initially optimized benzyl group, attached to the basic nitrogen, was found to be advantageously replaced by a cyclohexyl group, showing that an aromatic residue does not represent a prerequisite for activity.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/07/20 alle ore 23:04:44