Synthesis and Biological Evaluation of Potent Benzoselenophene and Heteroaromatic Analogues of ()-1-(chloromethyl)-8-methoxy-2,3-dihydro-1-benzo[]indol-5-ol (-MCBI)

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 9

PMID 35528410

Authors

Amol B Mhetre

Eppakayala Sreedhar

Rashmi Dubey

Ganesh A Sable

Hangeun Lee

Heekyoung Yang

Kyoungmin Lee

Do-Hyun Nam

Dongyeol Lim

Affiliations

Soon will be listed here.

Abstract

A diverse series of compounds (18a-x) were synthesized from ()-1-(chloromethyl)-8-methoxy-2,3-dihydro-1-benzo[]indol-5-ol (-MCBI) and benzoselenophene or heteroaromatic acids. These new compounds were evaluated for their cytotoxicity against the human gastric NCI-N87 and human ovarian SK-OV3 cancer cell lines. The incorporation of a methoxy substituent at the C-7 position of the -CBI unit enhances the cytotoxicity through its additional van der Waals interaction and gave a much higher potency than the corresponding -CBI-based analogues. Similarly, the -MCBI-benzoselenophene conjugates (18h-x) exhibited substitution effects on biological activity, and the -butyramido and -methylthiopropanamido analogues are highly potent, possessing >77- and >24-fold better activity than -MCBI-TMI for the SK-OV3 and NCI-N87 cell lines, respectively.

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