Issue 6, 2024

Mo-catalyzed cyclization of N-vinylindoles and skatoles: synthesis of dihydroindolo[1,2-c]-quinazolines and dihydroindolo[3,2-b]-indoles, and evaluation of their anticancer activities

Abstract

A novel approach has been developed for synthesizing unexpected dihydroindolo[1,2-c]-quinazolines (DINQ) and dihydroindolo[3,2-b]indole (DINI) compounds using N-vinylazoles as starting materials. The presence of a Mo-catalyst was found to be essential for the formation of DINQs from skatole derivatives and for accelerating the cyclization of DINI precursors. Biological evaluation revealed that compound 3o, a 2-phenyl-1-(1-phenylvinyl)-1H-indole derivative and DINI analog 6g exhibited nanomolar cytotoxic effects in vitro against a human colon cancer cell line (HCT-116).

Graphical abstract: Mo-catalyzed cyclization of N-vinylindoles and skatoles: synthesis of dihydroindolo[1,2-c]-quinazolines and dihydroindolo[3,2-b]-indoles, and evaluation of their anticancer activities

Supplementary files

Article information

Article type
Research Article
Submitted
27 Nov 2023
Accepted
08 Feb 2024
First published
08 Feb 2024
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2024,11, 1668-1677

Mo-catalyzed cyclization of N-vinylindoles and skatoles: synthesis of dihydroindolo[1,2-c]-quinazolines and dihydroindolo[3,2-b]-indoles, and evaluation of their anticancer activities

S. Pecnard, X. Liu, O. Provot, P. Retailleau, C. Tran and A. Hamze, Org. Chem. Front., 2024, 11, 1668 DOI: 10.1039/D3QO01973J

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