查耳酮和5-脱氧黄酮的合成及细胞毒性
Synthesis and cytotoxicity of chalcones and 5-deoxyflavonoids.
作者信息
Zhang Jing, Fu Xin-Ling, Yang Nan, Wang Qiu-An
机构信息
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China.
出版信息
ScientificWorldJournal. 2013 Jun 6;2013:649485. doi: 10.1155/2013/649485. Print 2013.
Chalcones 18 and 5-deoxyflavonoids 922 were synthesized in good yields by aldol condensation, Algar-Flynn-Oyamada reaction, glycosidation, and deacetylation reaction, respectively, starting from 2-acetyl phenols substituted by methoxy or methoxymethoxy group and appropriately benzaldehydes substituted by methoxy, methoxymethoxy group, or chlorine. Among them, 13 and 17~22 are new compounds. The cytotoxicity bioassays of these chalcones and 5-deoxyflavonoids were screened using the sulforhodamine B (SRB) protein staining method, and the results showed that compounds 2, 4, 5, 6, 10, 15, and 19 exhibited moderate cytotoxicity against the cancer cell line of MDA-MB-231, U251, BGC-823, and B16 in comparison with control drugs (HCPT, Vincristine, and Taxol).
分别以甲氧基或甲氧基甲氧基取代的2-乙酰基苯酚和甲氧基、甲氧基甲氧基或氯取代的适当苯甲醛为原料，通过羟醛缩合、阿尔加-弗林-小山反应、糖苷化反应和脱乙酰反应，以良好的产率合成了查耳酮18和5-脱氧黄酮922。其中，13和17~22为新化合物。采用磺酰罗丹明B（SRB）蛋白染色法对这些查耳酮和5-脱氧黄酮进行细胞毒性生物测定，结果表明，与对照药物（羟基喜树碱、长春新碱和紫杉醇）相比，化合物2、4、5、6、10、15和19对MDA-MB-231、U251、BGC-823和B16癌细胞系表现出中等细胞毒性。
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