Chemo- and Diastereoselective Cycloisomerization/[2 + 3] Cycloaddition of Enynamides: Synthesis of Spiropyrazolines
Huaying Fang1, Yang Li1, Lan Zhang2
1State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China.
Abstract:
A silver-catalyzed one-pot cycloisomerization/[2 + 3] cycloaddition of enynamides with in situ generated nitrile imines has been developed. Unlike the well-established cycloisomerization/[4 + n] cycloadditions of enynamides, this strategy provides efficient access to a new type of spiropyrazolines, which exhibit an anti-proliferation effect on multiple tumor cell lines. The compound 3u exhibits obvious anticancer activity by inducing apoptosis in RKO cells. The combination of compound 3u and an autophagy inhibitor could improve its anti-proliferation capacities.
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