RESUMO
New carbocyclic nucleosides with purine (compounds 3a and 3b), and 8-azapurine (compounds 3c and 3d) as base were prepared and assayed for in vitro activity.
Assuntos
Antivirais/síntese química , Antivirais/farmacologia , Nucleosídeos de Purina/síntese química , Nucleosídeos de Purina/farmacologia , Xilose/análogos & derivados , Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Conformação Molecular , Purinas/síntese química , Purinas/farmacologia , Xilose/síntese química , Xilose/farmacologiaRESUMO
Five new carbocyclic nucleosides were prepared by constructing a guanine (compounds 3, 5) or 8-azaguanine (compounds 4, 6, and 7) base on the amino group of (1'S,3'R)-3-(3'-amino-2',2'-dimethylcyclobutyl)propan-1-ol (8), and their activities against a variety of viruses and tumor cell lines were determined. Only compounds 3 and 7 showed a detectable activity at subtoxic concentrations against some viruses tested.
Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Antivirais/síntese química , Antivirais/farmacologia , Nucleosídeos/síntese química , Nucleosídeos/farmacologia , Ciclobutanos/síntese química , Ciclobutanos/farmacologia , Células Tumorais Cultivadas/efeitos dos fármacos , Vírus/efeitos dos fármacosRESUMO
Cyclobutyl nucleoside analogues containing guanine and 8-azaguanine (compounds 5-10) were prepared from (1R,cis)-3-aminomethyl-2,2-dimethylcyclobutylmethanol (1). All were evaluated as antiviral and antitumoral agents in a variety of assay systems. Compounds 6 and 7 showed a noteworthy activity against a respiratory syncytial virus and compound 10 was moderately active against vaccinia virus. Only compound 5 showed some cytostatic activity.
Assuntos
Antineoplásicos/síntese química , Antivirais/síntese química , Ciclobutanos/síntese química , Guanosina/síntese química , Antineoplásicos/farmacologia , Antivirais/farmacologia , Ciclobutanos/farmacologia , Enterovirus Humano B/efeitos dos fármacos , Guanosina/análogos & derivados , Guanosina/farmacologia , Vírus Sinciciais Respiratórios/efeitos dos fármacos , Espectrofotometria Infravermelho , Vaccinia virus/efeitos dos fármacosRESUMO
Six new carbocyclic nucleosides were prepared by mounting a purine (compounds 4-6), 8-azapurine (7 and 8) or uridine (9) base on the amino group of (1S,3R)-3-amino-2,2,3-trimethylcyclopentylmethanol (10). At subtoxic concentrations, compounds 5-9 showed at best marginal antiviral activity.
Assuntos
Adenosina/síntese química , Antivirais/síntese química , Ciclopentanos/química , Nucleosídeos/síntese química , Uridina/síntese química , Adenosina/análogos & derivados , Adenosina/química , Adenosina/farmacologia , Animais , Antivirais/química , Antivirais/farmacologia , Divisão Celular/efeitos dos fármacos , Chlorocebus aethiops , Vírus de DNA/efeitos dos fármacos , Células HeLa , Humanos , Vírus de RNA/efeitos dos fármacos , Estereoisomerismo , Relação Estrutura-Atividade , Linfócitos T/virologia , Uridina/análogos & derivados , Uridina/química , Uridina/farmacologia , Células VeroRESUMO
Six new carbocyclic nucleosides were prepared by mounting a purine (compounds 5-7), 8-azapurine (compounds 9 and 10) or pyrimidine (compound 13) base on the amino group of (1R,cis)-3-(aminomethyl)-1,2,2-trimethylcyclopentylmethanol (2). The antiviral activity of compounds 5-7, 10 and 13, and their cytostatic activity, were evaluated. At subtoxic concentrations, the compounds showed no or marginal antiviral activity. Compound 5 showed moderate inhibition on tumor cell proliferation.