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Bioorg Med Chem Lett ; 16(4): 1010-3, 2006 Feb 15.
Artículo en Inglés | MEDLINE | ID: mdl-16321530

RESUMEN

Several 1-[(2-hydroxy-ethoxy)methyl]-3-carbethoxy-4(1H)quinolones (2a-l) and l-[(2-hydroxy-ethoxy)methyl]-4(1H)quinolone-3-carboxylic acids (3a-j and 3l) were synthesized and 2a-j, 2l and 3a-j, 3l were evaluated against herpes simplex virus type 1 (HSV-1), employing a one-pot reaction: silylation of the desired quinolone (BSTFA 1% TMCS) followed by equimolar amount addition of 1,3-dioxolane, chlorotrimethylsilane and KI, at room temperature. The acyclonucleosides 2a-l were obtained in 40-77% yields. The esters 2a-j and 2l were subsequently converted into the corresponding hydroxyacids 3 in 40-70% yields. Attempts of hydrolysis of 2k produced only a mixture of degradation products. Antiviral activity of 2 and 3 on HSV-1 virus infection was assessed by the virus yield assay. Except for compounds 2i and 3e, the acyclonucleosides were found to reduce the virus yield by 70-99% at the concentration of 50 microM, being the acids, in general, more effective inhibitors than their corresponding esters. Compounds 3j and 2d exhibited antiviral activity against HSV-1 virus with EC50 of 0.7+/-0.04 and 0.8+/-0.09 microM, respectively. Both compounds were not toxic towards the Vero cell line.


Asunto(s)
Aciclovir , Antivirales , Herpesvirus Humano 1/efectos de los fármacos , Aciclovir/análogos & derivados , Aciclovir/síntesis química , Aciclovir/farmacología , Animales , Antivirales/síntesis química , Antivirales/química , Antivirales/farmacología , Chlorocebus aethiops , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Relación Estructura-Actividad , Células Vero/efectos de los fármacos , Células Vero/virología
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