Synthesis and Antitumour Activity of the Primin (2-methoxy-6-n-pentyl-1,4-benzoquinone) and Analogues

Author(s): D.J. Brondani, C.R.M. Nascimento, D.R. de M. Moreira, A.C. Lima Leite, I.A. de Souza, L.W. Bieber

Journal Name: Medicinal Chemistry

Volume 3 , Issue 4 , 2007

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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-benzoquinone), 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-tetrahydropyranyl) 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.

Keywords: Primin derivative, benzoquinone, antitumour agent, prodrug

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Article Details

Year: 2007
Page: [369 - 372]
Pages: 4
DOI: 10.2174/157340607781024410
Price: $65

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