期刊
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
卷 92, 期 -, 页码 439-448出版社
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2015.01.007
关键词
Prenyled chalcones; Geranylated chalcones; Antitumor agents; K562 cell; Apoptosis
资金
- National Natural Science Foundation of China [21202118, 31301142]
- International Science & Technology Cooperation Program of China [2013DFA31160]
- Ministry of Education Changjiang Scholars and Innovative Research Team Development Plan [IRT1166]
Four natural chalcones bearing prenyl or geranyl groups, i.e., bavachalcone (la), xanthoangelol (lb), isobavachalcone (1c), and isoxanthoangelol (1d) were synthesized by using a regio-selective iodination and the Suzuki coupling reaction as key steps. The first total synthesis of isoxanthoangelol (1d) was achieved in 36% overall yield. A series of diprenylated and digeranylated chalcone analogs were also synthesized by alkylation, regio-selective iodination, aldol condensation, Suzuki coupling and [1,3]-sigmatropic rearrangement. The structures of the 11 new derivatives were confirmed by H-1 NMR, C-13 NMR and HRMS. The anticancer activity of these new chalcone derivatives against human tumor cell line K562 were evaluated by MTT assay in vitro. SAR studies suggested that the 5'-prenylation/geranylation of the chalcones significantly enhance their cytotoxic activity. Among them, Bavachalcone (1a) displayed the most potent cytotoxic activity against K562 with IC50 value of 2.7 mu M. The morphology changes and annexin-V/PI staining studies suggested that those chalcone derivatives inhibited the proliferation of K562 cells by inducing apoptosis. (C) 2015 Elsevier Masson SAS. All rights reserved.
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