CF3SO2Na-Mediated, UV-Light-Induced Friedel-Crafts Alkylation of Indoles with Ketones/Aldehydes and Bioactivities of Products

Tianbao Yang; Huiai Lu; Yixuan Shu; Yifeng Ou; Ling Hong; Chak-Tong Au; Renhua Qiu

doi:10.1021/acs.orglett.9b04272

CF₃SO₂Na-Mediated, UV-Light-Induced Friedel-Crafts Alkylation of Indoles with Ketones/Aldehydes and Bioactivities of Products

Org Lett. 2020 Feb 7;22(3):827-831. doi: 10.1021/acs.orglett.9b04272. Epub 2020 Jan 8.

Authors

Tianbao Yang¹, Huiai Lu², Yixuan Shu², Yifeng Ou¹, Ling Hong², Chak-Tong Au³, Renhua Qiu¹

Affiliations

¹ State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering , Hunan University , Changsha 410082 , P. R. China.
² College of Biology , Huazhong University of Science and Technology , Wuhan 430074 , Hubei , P. R. China.
³ College of Chemistry and Chemical Engineering , Hunan Institute of Engineering , Xiangtan 411104 , Hunan , P. R. China.

PMID: 31913641
DOI: 10.1021/acs.orglett.9b04272

Abstract

A concise, one-step route to produce 3,3'-diindolylmethanes (DIMs) from simple indoles and ketones or aldehydes is reported. The key step is the ready formation of indole derivatives that involves the in situ conversion of CF₃SO₂Na reagent to ·CF₃ under oxygen or air (1.0 atm) and UV irradiation. It is disclosed that most of the obtained DIMs show anticancer activities in human bladder cancer cell lines EJ and T24.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Alkylation
Indoles / chemical synthesis
Indoles / chemistry*
Ketones / chemistry*
Molecular Structure
Stereoisomerism
Ultraviolet Rays*

Substances

Aldehydes
Indoles
Ketones
3,3'-diindolylmethane