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J Org Chem. 2013 Nov 1;78(21):10802-11. doi: 10.1021/jo4017887. Epub 2013 Oct 23.

Gold(I)-catalyzed cascade approach for the synthesis of tryptamine-based polycyclic privileged scaffolds as α1-adrenergic receptor antagonists.

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  • 1CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.


An efficient and facile gold(I)-catalyzed one-pot cascade protocol has been developed for the synthesis of tryptamine-fused polycyclic privileged structures through the treatment of substituted tryptamines and 2-ethynylbenzoic acids or 2-ethynylphenylacetic acids. This strategy features the formation of one C-C bond and two C-N bonds with high yields and broad substrate tolerance. The selected reduced target molecules are validated to perform as α1-adrenergic receptors antagonists. The most potent one, 4bh, exhibits an IC50 value of 277 nM on α1A subtype with a selectivity ratio of 15.8 over α1B subtype.

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