Gold(I)-Catalyzed Cascade Approach for the Synthesis of Tryptamine-Based Polycyclic Privileged Scaffolds as alpha(1)-Adrenergic Receptor Antagonists

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 formatio...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 78; no. 21; pp. 10802 - 10811
Main Authors Li, Zeng, Li, Jing, Yang, Nan, Chen, Ying, Zhou, Yu, Ji, Xun, Zhang, Lei, Wang, Jinfang, Xie, Xin, Liu, Hong
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 01.11.2013
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BENIGN PROSTATIC HYPERPLASIA
GOLD
LIGANDS
ANALOGS
SELECTIVE PDE5 INHIBITOR
URINARY-TRACT SYMPTOMS
ALZHEIMERS-DISEASE
DRUG DISCOVERY
INDOLE ALKALOIDS
AFFINITIES
Online AccessGet full text

Cover

More Information
Summary: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 alpha(1)-adrenergic receptors antagonists. The most potent one, 4bh, exhibits an IC50 value of 277 nM on alpha(1A) subtype with a selectivity ratio of 15.8 over alpha(1B) subtype.
ISSN:0022-3263
DOI:10.1021/jo4017887