One-Pot Synthesis of 2-Styrylindoles from Ortho-Substituted Chloroenynes

Guangkuan Zhao; Jerôme Bignon; Helène Levaique; Joëlle Dubois; Mouad Alami; Olivier Provot

doi:10.1021/acs.joc.8b02563

One-Pot Synthesis of 2-Styrylindoles from Ortho-Substituted Chloroenynes

J Org Chem. 2018 Dec 21;83(24):15323-15332. doi: 10.1021/acs.joc.8b02563. Epub 2018 Dec 11.

Authors

Guangkuan Zhao¹, Jerôme Bignon², Helène Levaique², Joëlle Dubois², Mouad Alami¹, Olivier Provot¹

Affiliations

¹ Univ. Paris-Sud, BioCIS, CNRS, University Paris-Saclay, Equipe Labellisée Ligue Contre Le Cancer, F-92296 Châtenay-Malabry , France.
² CIBI Platform , Institut de Chimie des Substances Naturelles , UPR 2301, CNRS avenue de la terrasse , F-91198 Gif sur Yvette , France.

PMID: 30520637
DOI: 10.1021/acs.joc.8b02563

Abstract

A facile one-pot synthesis of 2-styrylindoles, through Suzuki arylation of ortho-substituted chloroenynes followed by N-cyclization and N-demethylation, has been developed. A variety of 2-styrylindoles were obtained in good to excellent yields and were evaluated for their anticancer properties.

Publication types

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

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Chemistry Techniques, Synthetic
HCT116 Cells
Humans
Indoles / chemical synthesis*
Indoles / chemistry
Indoles / pharmacology*
Isomerism
Styrene / chemistry*

Substances

Antineoplastic Agents
Indoles
Styrene