Design and Synthesis of Some Novel Derivatives of (E)‐2‐(Benzo[d]thiazol‐2‐yl)‐3‐heteroaryl Acrylonitriles and Evaluation of Their Potential Anticancer Activity

This study presents an eco-friendly one-pot synthesis of (E)-2-(benzo[d]thiazol-2-yl)-3–acrylonitrile derivatives using [(BMIM)Ac] ionic liquid (IL) catalyst. The method achieves high yields, rapid reactions, and simple workup. Notably, selected compounds exhibit significant anticancer activity against A549 lung carcinoma cells, supported by in vitro and in silico analyses targeting apoptosis-related proteins, highlighting their potential as future anticancer agents.

Abstract

A proficient and environmentally friendly approach for the synthesis of substituted (E)-2-(benzo[d]thiazol-2-yl)-3-acrylonitrile (3a–3r) is described. This one-pot condensation employs 2-(benzo[d]thiazol-2-yl) acetonitrile (1) and diverse substituted aromatic aldehydes (2), using ethanol and the basic ionic liquid (IL) 1-butyl-3-methylimidazolium acetate [(BMIM)Ac] as a catalyst. This approach offers biologically significant heterocycles via Knoevenagel condensation. This approach's key features are an IL catalyst, exceptional yields, fast reaction times, versatility with various substrates, a unique reaction profile, and an uncomplicated workup process, as the final product can be readily isolated through simple filtration. The synthesized compounds 3m, 3d, 3p, 3q, and 3r showed promising anticancer activity against A549 lung carcinoma cell lines. The scratch assays provided compelling evidence of the antiproliferative activities of these compounds. In silico investigations indicate that these chemicals target critical proteins associated with apoptosis, a hallmark of cancer. In the future, the synthesized compounds may have potential as anticancer candidates.

Zum Volltext