90632-20-5Relevant articles and documents
Total Synthesis of the Neuroprotective Agent Cudraisoflavone J
Lu, Qili,Harmalkar, Dipesh S.,Quan, Guofeng,Kwon, Haeun,Cho, Jungsook,Choi, Yongseok,Lee, Dongho,Lee, Kyeong
, p. 1359 - 1365 (2021/05/07)
Cudraisoflavone J (1), isolated fromCudrania tricuspidata, is a potent neuroprotective compound with a chiral center. Herein, we report the first total synthesis of racemic cudraisoflavone J (1) using a Claisen rearrangement and a Suzuki coupling reaction as the key steps. Racemic secondary alcohol was kinetically resolved to give (+)- and (?)-cudraisoflavone J with up to 97 and 88% enantiomeric excess, respectively. The modified Mosher’s method was used to elucidate the absolute configuration of naturally occurring cudraisoflavone J.
Synthesis and antiangiogenic activity study of new hop chalcone Xanthohumol analogues
Nuti, Elisa,Bassani, Barbara,Camodeca, Caterina,Rosalia, Lea,Cantelmo, AnnaRita,Gallo, Cristina,Baci, Denisa,Bruno, Antonino,Orlandini, Elisabetta,Nencetti, Susanna,Noonan, Douglas M.,Albini, Adriana,Rossello, Armando
, p. 890 - 899 (2017/07/26)
Angiogenesis induction is a hallmark of cancer. Antiangiogenic properties of Xanthohumol (XN), a naturally occurring prenylated chalcone from hops, have been widely reported. Here we describe the synthesis and study the antiangiogenic activity in vitro of
Synthesis of xanthohumol analogues and discovery of potent thioredoxin reductase inhibitor as potential anticancer agent
Zhang, Baoxin,Duan, Dongzhu,Ge, Chunpo,Yao, Juan,Liu, Yaping,Li, Xinming,Fang, Jianguo
supporting information, p. 1795 - 1805 (2015/04/27)
The selenoprotein thioredoxin reductases (TrxRs) are attractive targets for anticancer drugs development. Xanthohumol (Xn), a naturally occurring polyphenol chalcone from hops, has received increasing attention because of its multiple pharmacological activities. We synthesized Xn and its 43 analogues and discovered that compound 13n displayed the highest cytotoxicity toward HeLa cells (IC50 = 1.4 μM). Structure-activity relationship study indicates that the prenyl group is not necessary for cytotoxicity, and introducing electron-withdrawing group, especially on the meta-position, is favored. In addition, methylation of the phenoxyl groups generally improves the potency. Mechanistic study revealed that 13n selectively inhibits TrxR and induces reactive oxygen species and apoptosis in HeLa cells. Cells overexpressing TrxR are resistant to 13n insult, while knockdown of TrxR sensitizes cells to 13n treatment, highlighting the physiological significance of targeting TrxR by 13n. The clarification of the structural determinants for the potency would guide the design of novel potent molecules for future development.
