Identification of the stereochemical requirements in the 4-aryl-2-cycloalkylidenhydrazinylthiazole scaffold for the design of selective human monoamine oxidase B inhibitors (Articolo in rivista)

Type
Label
  • Identification of the stereochemical requirements in the 4-aryl-2-cycloalkylidenhydrazinylthiazole scaffold for the design of selective human monoamine oxidase B inhibitors (Articolo in rivista) (literal)
Anno
  • 2014-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.bmc.2014.03.042 (literal)
Alternative label
  • M. D'Ascenzio, S. Carradori, D. Secci, L. Mannina, A.P. Sobolev, C. De Monte, R. Cirilli, M. Yanez, S. Alcaro, F. Ortuso (2014)
    Identification of the stereochemical requirements in the 4-aryl-2-cycloalkylidenhydrazinylthiazole scaffold for the design of selective human monoamine oxidase B inhibitors
    in Bioorganic & medicinal chemistry (Print); Elsevier, Amsterdam (Paesi Bassi)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • M. D'Ascenzio, S. Carradori, D. Secci, L. Mannina, A.P. Sobolev, C. De Monte, R. Cirilli, M. Yanez, S. Alcaro, F. Ortuso (literal)
Pagina inizio
  • 2887 (literal)
Pagina fine
  • 2895 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.scopus.com/inward/record.url?eid=2-s2.0-84899498676&partnerID=q2rCbXpz (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 22 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 8 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 10 (literal)
Note
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica e Tecnologie Del Farmaco, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy; Istituto Superiore di Sanità, Dipartimento Del Farmaco, V.le Regina Elena 299, 00161 Rome, Italy; Departamento de Farmacología, Universidad de Santiago de Compostela, Campus Universitario sur, E-15782 Santiago de Compostela (La Coruña), Spain; Dipartimento di Scienze della Salute, 'Magna Graecia' University of Catanzaro, Campus Universitario 'S. Venuta', Viale Europa Loc. Germaneto, 88100 Catanzaro, Italy; Istituto di Metodologie Chimiche, Laboratorio di Risonanza Magnetica 'Annalaura Segre', CNR, via Salaria km 29.300, 00015 Monterotondo, Rome, Italy (literal)
Titolo
  • Identification of the stereochemical requirements in the 4-aryl-2-cycloalkylidenhydrazinylthiazole scaffold for the design of selective human monoamine oxidase B inhibitors (literal)
Abstract
  • Exploring the effect that substituents on the cycloaliphatic ring had on the inhibitory activity against human monoamine oxidase B of a series of 4-aryl-2-cycloalkylidenhydrazinylthiazoles led to the synthesis of a new series of 2-methylcyclopentyl and 3-methylcyclopentyl derivatives which were tested in vitro as mixtures of diastereoisomers. In fact, due to the presence of a chiral center on the cycloaliphatic ring and a trisubstituted CN bond, they exist as four diastereoisomers ((E)-(R), (E)-(S), (Z)-(R), (Z)-(S)). 4-(2,4- Difluorophenyl)-2-(2-(3-methylcyclopentylidene)hydrazinyl)thiazole was chosen as a model to investigate the influence of stereochemical requirements on the inhibitory activity against hMAO-B of these derivatives after a stereoconservative synthesis and semi-preparative HPLC diastereoseparation. (R)-(Z) isomer of this compound was endowed with a potent and selective hMAO-B inhibition higher than that of reference drugs as also corroborated by molecular modeling studies. (literal)
Editore
Prodotto di
Autore CNR
Insieme di parole chiave

Incoming links:


Autore CNR di
Prodotto
Editore di
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi
Insieme di parole chiave di
data.CNR.it