A New Avenue toward Androgen Receptor Pan-antagonists: C2 Sterically Hindered Substitution of Hydroxy-propanamides (Articolo in rivista)

Type
Label
  • A New Avenue toward Androgen Receptor Pan-antagonists: C2 Sterically Hindered Substitution of Hydroxy-propanamides (Articolo in rivista) (literal)
Anno
  • 2014-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jm5005122 (literal)
Alternative label
  • Guerrini, Andrea; Tesei, Anna; Ferroni, Claudia; Paganelli, Giulia; Zamagni, Alice; Carloni, Silvia; Di Donato, Marzia; Castoria, Gabriella; Leonetti, Carlo; Porru, Manuela; De Cesare, Michelandrea; Zaffaroni, Nadia; Beretta, Giovanni Luca; Del Rio, Alberto; Varchi, Greta (2014)
    A New Avenue toward Androgen Receptor Pan-antagonists: C2 Sterically Hindered Substitution of Hydroxy-propanamides
    in Journal of medicinal chemistry
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Guerrini, Andrea; Tesei, Anna; Ferroni, Claudia; Paganelli, Giulia; Zamagni, Alice; Carloni, Silvia; Di Donato, Marzia; Castoria, Gabriella; Leonetti, Carlo; Porru, Manuela; De Cesare, Michelandrea; Zaffaroni, Nadia; Beretta, Giovanni Luca; Del Rio, Alberto; Varchi, Greta (literal)
Pagina inizio
  • 7263 (literal)
Pagina fine
  • 7279 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 57 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 17 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 17 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Italian National Research Council- Institute of Organic Synthesis and Photoreactivity; Istituto Scientifico Romagnolo per lo Studio e la Cura dei Tumori; Seconda Universita degli Studi di Napoli; Istituto Regina Elena Roma; Fondazione IRCCS Istituto Nazionale Tumori Milano (literal)
Titolo
  • A New Avenue toward Androgen Receptor Pan-antagonists: C2 Sterically Hindered Substitution of Hydroxy-propanamides (literal)
Abstract
  • The androgen receptor (AR) represents the primary target for prostate cancer (PC) treatment even when the disease progresses toward androgen-independent (AIPC) or castration-resistant (CRPC) forms. Because small chemical changes in the structure of nonsteroidal AR ligands determine the pharmacological responses of AR, we developed a novel stereoselective synthetic strategy that allows sterically hindered C2-substituted bicalutamide analogues to be obtained. Biological and theoretical evaluations demonstrate that C2-substitution with benzyl and phenyl moieties is a new, valuable option toward improving pan-antagonist behavior. Among the synthesized compounds, (R)-16m, when compared to casodex, (R)-bicalutamide, and enzalutamide, displayed very promising in vitro activity toward five different prostate cancer cell lines, all representative of CPRC and AIPC typical mutations. Despite being less active than (R)-bicalutamide, (R)-16m also displayed marked in vivo antitumor activity on VCaP xenografts and thus it may serve as starting point for developing novel AR pan-antagonists. (literal)
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