Department of Medicinal Chemistry, Center for Pharmaceutical Research and Development, School of Pharmacy, Southwest Medical University, Luzhou, Sichuan, 646000, PRC.
Department of Chemistry, University of Virginia, Charlottesville, VA, 22904-4319, USA.
Chembiochem. 2018 Nov 2;19(21):2293-2299. doi: 10.1002/cbic.201800458. Epub 2018 Oct 12.
A chiral amino alcohol based ligand was found to promote the highly enantioselective addition of terminal conjugated diynes to aromatic and aliphatic aldehydes. The combination of easily available C -symmetric (R)- and (S)-BINOL with Ti(OiPr) , Zn powder, and EtI was also found to catalyze the asymmetric addition of 1,3-diynes to aldehydes under mild reaction conditions, and thus, both enantiomers of the chiral conjugated diynols could be prepared with high enantioselectivities. The resulting optically active conjugated diynols were found to have potential anticancer activities with significant differences against HepG2 and HeLa cancer cells, and remarkable enantioselective cytotoxicity was observed for the first time.
一种手性氨基醇配体被发现能促进末端共轭二炔与芳香族和脂肪族醛的高对映选择性加成。还发现，容易获得的 C 对称 (R)-和 (S)-BINOL 与 Ti(OiPr) 、Zn 粉和 EtI 一起，可以在温和的反应条件下催化 1,3-二炔与醛的不对称加成，因此，手性共轭二炔醇的两种对映异构体都可以以高对映选择性制备。所得到的手性共轭二炔醇被发现具有潜在的抗癌活性，对 HepG2 和 HeLa 癌细胞有显著差异，并且首次观察到显著的对映选择性细胞毒性。
