Several 1,3-thiazolidin-4-ones bearing a 2,6-dihalophenyl group at C-2 and a substituted pyrimidin-2-yl ring at the N-3 were synthesised and evaluated as anti-HIV agents. The results of the in vitro tests showed that some of them were highly effective inhibitors of human immunodeficiency virus type-1 (HIV-1) replication at 10–40 nM concentrations with minimal cytotoxicity. Structure–activity relationship studies revealed that the nature of the substituents at the 2 and 3 positions of the thiazolidinone nucleus had a significant impact on the in vitro anti-HIV activity of this class of potent antiretroviral agents. The compounds had significantly reduced activity against the characteristic NNRTI-resistant virus mutants (bearing the K103N and Y181C RT mutations), thereby acting as non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors (NNRTIs).

RAO A, BALZARINI J, CARBONE A, CHIMIRRI A, DE CLERCQ E, MONFORTE AM, et al. (2004). 2-(2,6-dihalophenyl)-3-(pyrimidin-2-yl)-1,3-thiazolidin-4-ones as nonnucleoside HIV-1 reverse trascriptase inhibitors. ANTIVIRAL RESEARCH, 63(2), 79-84 [10.1016/j.antiviral.2004.03.004].

2-(2,6-dihalophenyl)-3-(pyrimidin-2-yl)-1,3-thiazolidin-4-ones as nonnucleoside HIV-1 reverse trascriptase inhibitors

CARBONE, Anna;
2004-01-01

Abstract

Several 1,3-thiazolidin-4-ones bearing a 2,6-dihalophenyl group at C-2 and a substituted pyrimidin-2-yl ring at the N-3 were synthesised and evaluated as anti-HIV agents. The results of the in vitro tests showed that some of them were highly effective inhibitors of human immunodeficiency virus type-1 (HIV-1) replication at 10–40 nM concentrations with minimal cytotoxicity. Structure–activity relationship studies revealed that the nature of the substituents at the 2 and 3 positions of the thiazolidinone nucleus had a significant impact on the in vitro anti-HIV activity of this class of potent antiretroviral agents. The compounds had significantly reduced activity against the characteristic NNRTI-resistant virus mutants (bearing the K103N and Y181C RT mutations), thereby acting as non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors (NNRTIs).
2004
RAO A, BALZARINI J, CARBONE A, CHIMIRRI A, DE CLERCQ E, MONFORTE AM, et al. (2004). 2-(2,6-dihalophenyl)-3-(pyrimidin-2-yl)-1,3-thiazolidin-4-ones as nonnucleoside HIV-1 reverse trascriptase inhibitors. ANTIVIRAL RESEARCH, 63(2), 79-84 [10.1016/j.antiviral.2004.03.004].
File in questo prodotto:
File Dimensione Formato  
antiviralresearch2004.pdf

Solo gestori archvio

Descrizione: Articolo
Dimensione 73.07 kB
Formato Adobe PDF
73.07 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/17927
Citazioni
  • ???jsp.display-item.citation.pmc??? 6
  • Scopus 118
  • ???jsp.display-item.citation.isi??? 112
social impact