5-Alkyl-6-benzyl-2-(2-oxo-2-phenylethylsulfanyl)pyrimidin-4(3H)-ones, a series of anti-HIV-1 agents of the dihydro-alkoxy-benzyl-oxopyrimidine family with peculiar structure-activity relationship profile. (Articolo in rivista)

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

Label

• 5-Alkyl-6-benzyl-2-(2-oxo-2-phenylethylsulfanyl)pyrimidin-4(3H)-ones, a series of anti-HIV-1 agents of the dihydro-alkoxy-benzyl-oxopyrimidine family with peculiar structure-activity relationship profile. (Articolo in rivista) (literal)

Anno

• 2008-01-01T00:00:00+01:00 (literal)

Alternative label

• Nawrozkij MB, Rotili D, Tarantino D, Botta G, Eremiychuk AS, Musmuca I, Ragno R, Samuele A, Zanoli S, Armand-Ugón M, Clotet-Codina I, Novakov IA, Orlinson BS, Maga G, Esté JA, Artico M, Mai A. (2008)
  5-Alkyl-6-benzyl-2-(2-oxo-2-phenylethylsulfanyl)pyrimidin-4(3H)-ones, a series of anti-HIV-1 agents of the dihydro-alkoxy-benzyl-oxopyrimidine family with peculiar structure-activity relationship profile.
  in Journal of medicinal chemistry
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Nawrozkij MB, Rotili D, Tarantino D, Botta G, Eremiychuk AS, Musmuca I, Ragno R, Samuele A, Zanoli S, Armand-Ugón M, Clotet-Codina I, Novakov IA, Orlinson BS, Maga G, Esté JA, Artico M, Mai A. (literal)

Pagina inizio

• 4641 (literal)

Pagina fine

• 4652 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 51 (literal)

Rivista

• Journal of medicinal chemistry (Rivista)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• Volgograd State Technical University, Pr. Lenina, 28, 400131 Volgograd, Russia, Dipartimento di Studi Farmaceutici, Sapienza Universit di Roma, P. le A. Moro 5, 00185 Roma, Italy, Istituto di Genetica Molecolare IGM-CNR, via Abbiategrasso 207, 27100 Pavia, Italy, and Retrovirology Laboratory IrsiCaixa, Hospital Universitari Germans Trias i Pujol, Universitat Autnoma de Barcelona, 08916 Badalona, Spain (literal)

Titolo

• 5-Alkyl-6-benzyl-2-(2-oxo-2-phenylethylsulfanyl)pyrimidin-4(3H)-ones, a series of anti-HIV-1 agents of the dihydro-alkoxy-benzyl-oxopyrimidine family with peculiar structure-activity relationship profile. (literal)

Abstract

• A series of dihydro-alkylthio-benzyl-oxopyrimidines (S-DABOs) bearing a 2-aryl-2-oxoethylsulfanyl chain at pyrimidine C2, an alkyl group at C5, and a 2,6-dichloro-, 2-chloro-6-fluoro-, and 2,6-difluoro-benzyl substitution at C6 (oxophenethyl- S-DABOs, 6-8) is here described. The new compounds showed low micromolar to low nanomolar (in one case subnanomolar) inhibitory activity against wt HIV-1. Against clinically relevant HIV-1 mutants (K103N, Y181C, and Y188L) as well as in enzyme (wt and K103N, Y181I, and L100I mutated RTs) assays, compounds carrying an ethyl/ iso-propyl group at C5 and a 2,6-dichloro-/2-chloro-6-fluoro-benzyl moiety at C6 were the most potent derivatives, also characterized by low fold resistance ratio. Interestingly, the structure-activity relationship (SAR) data drawn from this DABO series are more related to HEPT than to DABO derivatives. These findings were at least in part rationalized by the description of a fair superimposition between the 6-8 and TNK-651 (a HEPT analogue) binding modes in both WT and Y181C RTs. (literal)

Prodotto di

• Institute of molecular genetics (IGM) (Istituto)
• Sviluppo e meccanismo d'azione di analoghi nucleotidici e nucleosidici come composti antiproliferativi e antivirali : nuovi composti e nuovi bersagli per la terapia (ME.P04.004.001) (Modulo)

Autore CNR

• SAMANTHA ZANOLI (Unità di personale esterno)
• GIOVANNI MAGA (Unità di personale interno)

Insieme di parole chiave

• Parole chiave di "5-Alkyl-6-benzyl-2-(2-oxo-2-phenylethylsulfanyl)pyrimidin-4(3H)-ones, a series of anti-HIV-1 agents of the dihydro-alkoxy-benzyl-oxopyrimidine family with peculiar structure-activity relationship profile." (Insieme di parole chiave)

Incoming links:

Prodotto

• Institute of molecular genetics (IGM) (Istituto)
• Sviluppo e meccanismo d'azione di analoghi nucleotidici e nucleosidici come composti antiproliferativi e antivirali : nuovi composti e nuovi bersagli per la terapia (ME.P04.004.001) (Modulo)

Autore CNR di

• GIOVANNI MAGA (Unità di personale interno)
• SAMANTHA ZANOLI (Unità di personale esterno)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Journal of medicinal chemistry (Rivista)

Insieme di parole chiave di

• Parole chiave di "5-Alkyl-6-benzyl-2-(2-oxo-2-phenylethylsulfanyl)pyrimidin-4(3H)-ones, a series of anti-HIV-1 agents of the dihydro-alkoxy-benzyl-oxopyrimidine family with peculiar structure-activity relationship profile." (Insieme di parole chiave)