RESUMEN
Based on fluorine switch approach, a series of 3'-fluoropenciclovir analogues with different purine and pyrimidine bases were designed and synthesized. Direct reduction of beta-fluoroester to the corresponding 3-fluoroalcohol provided an easy and new entry pathway towards the synthesis of 3'-fluoropenciclovir analogues. The synthesized 3'-fluoropenciclovir analogues were evaluated for their antiviral activities against the poliovirus, HSV-1, HSV-2 and HIV.
Asunto(s)
Aciclovir/análogos & derivados , Antivirales/síntesis química , Diseño de Fármacos , Aciclovir/síntesis química , Aciclovir/química , Aciclovir/farmacología , Antivirales/química , Antivirales/farmacología , VIH-1/efectos de los fármacos , Herpesvirus Humano 1/efectos de los fármacos , Herpesvirus Humano 2/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Poliovirus/efectos de los fármacosRESUMEN
[1'-Fluoro-2',2'-bis-(hydroxymethyl)cyclopropylmethyl]purines were designed, synthesized and their antiviral activity against poliovirus, HSV and HIV was evaluated.
Asunto(s)
Antivirales/síntesis química , Purinas/síntesis química , Antivirales/química , Antivirales/farmacología , Ciclopropanos/química , Ciclopropanos/farmacología , VIH/efectos de los fármacos , Herpesvirus Humano 1/efectos de los fármacos , Herpesvirus Humano 2/efectos de los fármacos , Estructura Molecular , Poliovirus/efectos de los fármacos , Purinas/química , Purinas/farmacología , Simplexvirus/efectos de los fármacos , Relación Estructura-ActividadRESUMEN
A novel carboacyclic nucleoside analogue, 9-[2-bromo-4-hydroxy-3-hydroxymethyl-2-butenyl] adenine, and its derivatives were designed and synthesized as open-chain analogues of neplanocin A. The syntheses were accomplished via the coupling of adenine or pyrimidine bases to the key intermediate allylic bromide 7. The bromide 7 was prepared from epichlorohydrin in a seven step process in a 54% overall yield. The synthesized compounds were evaluated for their antiviral activity against the polio virus, HSV and HIV.