CPA-catalyzed enantioselective synthesis of α,α-bisindoles-assembled triarylmethanes between 3-indolyl[1,4]thiazepines and indoles via ring-opening/friedel-crafts reaction.

IF 4.3 2区化学 Q2 CHEMISTRY, APPLIED

Molecular Diversity Pub Date : 2026-10-01 Epub Date: 2026-06-09 DOI:10.1007/s11030-026-11617-z

Teng Liu, Airong She, Fei Wang, Kaiquan Liu, Feixiang Cheng

引用次数: 0

Abstract

We describe that a type of new and flexible 3-indolyl[1,4]thiazepines can be efficiently merged with substituted indoles catalyzed by chiral phosphoric acid (CPA), providing a range of structurally diverse α,α-bisindoles-assembled triarylmethanes in excellent diastereomeric and enantiomeric excess (up to 92% de, > 99% ee), excellent yields, and 100% atom economy. These reactions harness the ability of 3-indolyl[1,4]thiazepines to form active species via a ring-opening process involving the cleavage of C-N bond that are subsequently trapped by nucleophilic indoles via Friedel-Crafts reaction. The late-stage modification, and identification of partial products exhibiting good anticancer activities highlights the utility of this methodology.

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cpa催化3-吲哚[1,4]噻吩与吲哚开环/friede -crafts反应对映选择性合成α，α-双吲哚组装三芳基甲烷。

我们描述了一种新的柔性3-吲哚[1,4]噻吩类化合物可以在手性磷酸（CPA）催化下与取代吲哚有效地结合，提供一系列结构多样的α，α-双吲哚组装的三芳基甲烷，具有优异的非对映体和对映体超额（高达92% de， > 99% ee），优异的产率和100%的原子经济性。这些反应利用了3-吲哚基[1,4]噻唑类药物的能力，通过一个涉及C-N键裂解的开环过程形成活性物质，这些活性物质随后通过Friedel-Crafts反应被亲核吲哚捕获。后期的修饰和部分产品的鉴定显示出良好的抗癌活性，突出了这种方法的实用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Molecular Diversity 化学-化学综合

CiteScore

7.30

自引率

7.90%

发文量

219

审稿时长

2.7 months

期刊介绍： Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;