Design and Synthesis of Some Novel Derivatives of ( <i>E</i> )‐2‐(Benzo[ <i>d</i> ]thiazol‐2‐yl)‐3‐heteroaryl Acrylonitriles and Evaluation of Their Potential Anticancer Activity
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.
Authors
- Aruna Sivaram (ORCID: https://orcid.org/0000-0003-4942-4114)
- Chandrakant K. Tagad (ORCID: https://orcid.org/0000-0002-3105-0743)
- Amol Kahandal
- Satish U. Deshmukh (ORCID: https://orcid.org/0000-0002-4594-7762)
- Ashishkumar P. Katariya (ORCID: https://orcid.org/0000-0003-1113-8366)
- A. R. Bhagat Patil (ORCID: https://orcid.org/0000-0002-2864-7784)
- Anant B. Kanagare (ORCID: https://orcid.org/0000-0002-6463-2926)
- Gajanan N. Wadje
Institutions
- Bansomdejchaopraya Rajabhat University (TH)
- G.S. Science, Arts And Commerce College (IN)
- MIT Art, Design and Technology University (IN)
Publication Details
- Journal
- ChemistrySelect
- Published
- 2025-08-26
- DOI
- https://doi.org/10.1002/slct.202500064
- Primary Topic
- Synthesis and biological activity
- Type
- article
- Field-Weighted Citation Impact
- 0.00