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Med Chem ; 3(4): 369-72, 2007 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-17627574

RESUMO

Cancer is a serious worldwide health threat, killing almost seven million people per year. Quinones are an important class of antitumour agents that are activated by tumour hypoxia. Primin (2-methoxy-6-n-pentyl-1,4-benzo-quinone), a naturally-occurring product obtained from Primula obconica (Primulaceae) has shown antimicrobial and antitumour properties. The synthesis of the Primin to obtain 3-, 5- or 6-alkyl substituted derivatives has been previously attempted seeking antitumour activity. The intermediate reaction products, 2-methoxy-hydroquinone-di-(2'-tetrahydro-pyranyl) ether and 2-methoxy-6-n-pentyl-hydroquinone-di-(2'-tetrahydropyranyl) ether were obtained and evaluated against sarcoma 180 (S-180) and Ehrlich carcinoma, as well as toxicity tests were performed. The antitumour activity tests showed that these intermediate compounds were able to inhibit S-180 sarcoma and Ehrlich carcinoma growth in mice. These results indicated that the tetrahydropyranyl protect group conserved the antitumour activity in comparison with quinone group, however, it exhibited a less toxic effect, with no characteristic of quinones. These results can suggest that compound 2-methoxy-6-n-pentyl-hydroquinone-di-(2'-tetrahydropyranyl) ether may act as a prodrug with some advantages in comparison with the Primin.


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Benzoquinonas/química , Benzoquinonas/farmacologia , Animais , Antineoplásicos/química , Comportamento Animal/efeitos dos fármacos , Benzoquinonas/síntese química , Masculino , Camundongos , Estrutura Molecular , Transplante de Neoplasias , Neoplasias/tratamento farmacológico , Neoplasias/patologia , Relação Estrutura-Atividade , Fatores de Tempo
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