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Synthesis of N-(4-acryloylphenyl)-2,4-dichloro-5-sulfamoylbenzamides with anticancer activity
* 1 , 2 , 3
1  Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Gdańsk, Gdańsk, Poland
2  Department of Organic Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland
3  Department of Biotechnology, Intercollegiate Faculty of Biotechnology, University of Gdańsk - Medical University of Gdańsk, Gdańsk, Poland
Academic Editor: Duke Wang


Breast, cervical and colorectal cancers are the most common female cancer types world-wide. One important approach in the search for chemotherapeutic agents is the combination of different building blocks, fragments from known drugs, leading structures, or "hit" structures into a single molecule. This strategy involves creating hybrid compounds that aim to achieve a synergistic effect and enhanced efficacy compared to the individual starting compounds [1].

The main aim of this research was to synthesize new N-(4-acryloylphenyl)-2,4-dichloro-5-sulfamoylbenzamide derivatives with potential anticancer activity. The compounds were designed as molecular hybrids, incorporating fragments of chalcone and benzenesulfonamide. The structures of the compounds were confirmed using elemental analysis, spectroscopic techniques such as (IR, 1H NMR, 13C NMR), and mass spectrometry.

MTT assays were performed on three cancer cell lines: MCF-7 (breast cancer), HCT-116 (colorectal cancer), and HeLa (cervical cancer). Results showed that all compounds 6-9 and 11-13 are highly active against all three cell lines and their IC50 are between 3 µM to 13 µM. The highest sensitivity shows HCT-116 cell line with IC50 values from 3 µM to 4 µM for all tested compounds. The highest cytotoxic activity present 8 and 11 with IC50 = 3 µM. Activity of compounds 6-9 and 11-13 is also high against cell lines MCF-7 and HeLa with IC50 = 4.5‒9 µM (MCF-7) and IC50 = 4‒13 µM (HeLa). Compound 9 shows the best results with average IC50 = 4 µM.

[1] Fortin S, et al. Expert Opin. Drug. Discov. 2013, 8, 1029–1047.

Keywords: sulfonamide; anticancer; cytotoxic; synthesis; breast cancer; colorectal cancer; cervical cance