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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Letter Article

An Efficient Multi-Functionalized Synthesis of N-Arylated Indole-3- Substituted-2-Benzimidazoles as Anticancer Agents

Author(s): Shaik Firoj Basha, Yeruva Pavankumar Reddy, Poorna Chandrasekhar Settipalli, Tangella Nagendra Prasad, Vadiga Shanthi Kumar, Gajula Mahaboob Basha, Varimadugu Aruna, Naveen Mulakayala and Shaik Anwar*

Volume 20, Issue 8, 2023

Published on: 16 March, 2023

Page: [701 - 710] Pages: 10

DOI: 10.2174/1570178620666230217111458

Price: $65

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Abstract

A convenient, efficient method for synthesising indole-3-substituted-2-benzimidazoles and benzothiazoles was carried out using N-arylation followed by condensation-oxidation protocol. Narylation of 1H-indole-3-carbaldehyde was carried out via CuI/DMED to yield 1-(3-((tertbutylsulfonyl) methyl)phenyl)-1H-indole-3-carbaldehyde. Condensation using various o-phenylenediamines in the presence of CAN/DMF as oxidant furnished the desired 2-(1-(3-((tert-butylsulfonyl) methyl)phenyl)-1H-indol-3-yl)-1H-benzo[d]imidazole. In addition to simple o-phenylenediamines, 1,2-arylenediamines substituted with withdrawing and donating groups, heterocyclic-2,3-phenylene diamines are well tolerated and give good yields of up to 74% yield. As simple reaction between ophenylenediamines and 1H-substituted indole-3-carboxyaldehyde give indole-3-substituted-2- benzimidazoles with moderate to good yields. These novel indole-derived benzimidazoles and benzothiazoles have shown their efficacy as anti-cancer agents with various cancer K-562, MDA-MB231, colon-205 cell lines.

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