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.