期刊
CHINESE CHEMICAL LETTERS
卷 20, 期 10, 页码 1141-1144出版社
ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2009.04.001
关键词
Betulinic acid; Betulin; Betulonic acid; 28-O-Alkylation; 28-O-Acylation; Cytotoxicity
28-Carboxymethoxy lupane tritepenoids 3 and 4 were synthesized by alkylation of betulin with the THP protected 2-hydroxyethyl iodide followed by oxidation and reduction. Direct reaction of betulin (5) or betulone (10) with ethyl bromoacetate led to 28-O-acylation, instead of 28-O-alkylation. The targeted compounds 3 and 4 were not cytotoxic at the highest concentration tested (75 mu mol/L), suggesting that elongation of the chain length at the 28-position in both betulinic acid (1) and betulonic acid (2) was detrimental to the cytotoxicity. The acylation products 28-O-bromoacetates (8a, 8b and 11) and 28-O-methoxyacetate 13 exhibited cytotoxicity against several cancer cell lines tested. (C) 2009 Ze Qi Xu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
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