Synthesis and cytotoxic evaluation of C-9 oxidized podophyllotoxin derivatives

被引:28
作者
Castro, Ma Angeles [1 ]
del Corral, Jos M. Miguel [1 ]
Gordaliza, Marina [1 ]
Garcia, Pablo A. [1 ]
Gomez-Zurita, Ma Antonia [1 ]
San Feliciano, Arturo [1 ]
机构
[1] Univ Salamanca, Fac Farm, Dept Quim Farmaceut, E-37007 Salamanca, Spain
关键词
podophyllotoxin; podophyllic aldehyde; C-9 oxidized cyclolignans; cytotoxicity;
D O I
10.1016/j.bmc.2006.12.008
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 [生物化学与分子生物学]; 081704 [应用化学];
摘要
A series of podophyllotoxin and podophyllic aldehyde derivatives, lacking the lactone ring and oxidized at C-9 position, has been prepared. The functionalities considered at C-9 were carboxylic acids and several derivatives such as esters, amides, nitriles or anhydrides. The synthesized compounds were cytotoxic at the micromolar level, though less potent and selective than the parent compounds, revealing the influence of the C-9 electrophilic character on the potency and selectivity of these cyclolignans. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1670 / 1678
页数:9
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