期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 14, 页码 9138-9150出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01098
关键词
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资金
- National Natural Science Foundation of China [81573588, 81773889, 21772131]
- Science & Technology Department of Sichuan Province [2017JZYD0001, 2017JQ0002, 2017JY0323]
Enantio- and diastereoselective synthesis of multifunctional spiropyrazolone scaffolds has been achieved using secondary amine-catalyzed [4 + 2] annulations of alpha,beta,gamma,delta,-unsaturated pyrazolones with aldehydes. The pyrazolone substrates serve as C4 synthons to produce 6-membered, carbocycle-based, chiral spiropyrazolone derivatives. The synthesized chiral compounds showed potent toxicity against a panel of cancer cell lines. The most potent compound 3h-induced cell cycle arrest and macroautophagy in HCT116 colorectal cancer cells, triggering autophagy-dependent apoptotic cell death.
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