62949-76-2Relevant articles and documents
Synthesis and anti-cancer activity evaluation of novel prenylated and geranylated chalcone natural products and their analogs
Wang, Hao-Meng,Zhang, Li,Liu, Jiang,Yang, Zhao-Liang,Zhao, Hong-Ye,Yang, Yao,Shen, Di,Lu, Kui,Fan, Zhen-Chuan,Yao, Qing-Wei,Zhang, Yong-Min,Teng, Yu-Ou,Peng, Yu
, p. 439 - 448 (2015/03/05)
Four natural chalcones bearing prenyl or geranyl groups, i.e., bavachalcone (1a), xanthoangelol (1b), 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 1H NMR, 13C 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 50-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 mM. The morphology changes and annexin-V/PI staining studies suggested that those chalcone derivatives inhibited the proliferation of K562 cells by inducing apoptosis.
Concise synthesis of prenylated and geranylated chalcone natural products by regiospecific iodination and Suzuki coupling reactions
Wang, Haomeng,Yan, Zhihong,Lei, Yanan,Sheng, Kai,Yao, Qingwei,Lu, Kui,Yu, Peng
supporting information, p. 897 - 899 (2014/02/14)
Four natural chalcones bearing prenyl or geranyl groups, i.e., isobavachalcone (1), bavachalcone (2), xanthoangelol (3), and 2′,4′,4-trihydroxy-5′-geranylchalcone (isoxanthoangelol, 4) were synthesized by using a regio-selective iodination and the Suzuki coupling reaction as key steps. Among them, the first total synthesis of 2′,4′,4-trihydroxy-5′-geranylchalcone was achieved in 36% overall yield. Comparing with the reported methods based on C-alkylation or O-alkylation followed by Claisen rearrangement to introduce the side chain, this new strategy capitalizes on a precious regiochemical control during iodination. The overall yields for the synthesis of the first three chalcones were improved from 17% to 53%, 12% to 35%, and 28% to 50%, respectively.
New synthetic routes to biologically interesting geranylated flavanones and geranylated chalcones: First total synthesis of (±)-prostratol F, xanthoangelol, and (±)-lespeol
Jung, Doo Hwan,Lee, Yong Rok,Kim, Sung Hong
experimental part, p. 635 - 647 (2010/07/02)
A new and efficient synthetic approach to biologically interesting geranylated flavanones and geranylated chalcones is described. Thus, the first total syntheses of the geranylated flavanones (±)-prostratol F (1), (±)-8-geranyl-3′,4′,7-trihydroxyflavanone (2), and (±)-6-geranyl-5,7-dihydroxy-3′,4′-dimethoxyflavanone (3) were carried out starting from 2,4-dihydroxyacetophenone (10) and 2,4,6-trihydroxyacethophenone (17) in five to six steps (Schemes 2 and 3). The geranylated chalcones xanthoangelol (4), 3-geranyl-2,3′,4,4′- tetrahydroxychalcone (5), (±)-lespeol (6), and lespeol derivatives (±)-7-9 were synthesized starting from 2,4-dihydroxyacetophenone (10) in three to four steps (Schemes 2 and 6).
