Synthesis and Studies of Anticancer and Antimicrobial Activity of New
Phenylurenyl Chalcone Derivatives

Güneş   Y.   Akdeniz; Hülya      Akgün; Özlem   B.   Özakpınar; Merve      Duracık; Mehmet      Öztürk; Evin      İşcan; Faika      Başoğlu

Abstract

Background: Phenylurenyl chalcone structures have the potential to act as a scaffold in anticancer drug discovery.

Methods: N-Phenethyl-N'-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}urea, 4/3-[(2E)-3-substitutedphenylprop-2- enoyl]phenyl}-N-phenylurea,4/3-[(2E)-3-substitutedphenyl.

prop-2-enoyl]phenyl}-N-methylphenyl urea and {4/3-[(2E)-3-substitutedphenylprop-2-enoyl]phenyl}-Nethylphenyl urea derivatives(1-35) were prepared and evaluated for their anticancer and antimicrobial activity against A-549 Hep-3B, HT-29, CF-7, PC-3, K-562 NIH-3T3 and Huh-7 cell lines and against Staphylococcus aureus (ATCC 6538), Pseudomonas aeruginosa (ATCC 9027), Escherichia coli (ATCC 8739) and Candida albicans (ATCC 10231), respectively.

Results: While compounds 2, 26, 29, and 34 showed moderate cytotoxic activity on cell line Huh 7, compounds 14 (IC₅₀: 6.42 μM), 16 (IC₅₀: 5.64 μM), 19 (IC₅₀: 6.95 μM) and 34 (IC₅₀: 6.87 μM) showed good cytotoxic activity on Huh-7 cell line close to Sorafenib (IC₅₀: 4.29 μM) (as reference). MIC values of compounds 4 and 22 against E. coli were 25 μg/ml, compounds 3, 14 and 29 against P. aeruginosa 25 μg/ml, and compounds 11 and 33 against S. aureus 25 μg/ml. On the other hand, the minimum inhibitory concentration of all tested compounds against C. albicans was 25 μg/ml.

Conclusion: N-Phenethyl-N'-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}urea may be a new candidate to be developed as an anticancer compound.

Keywords: Urea, phenylurenyl chalcone, kinase inhibitors, anticancer, antimicrobial, cytotoxicity.

Graphical Abstract

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Cite As

Letters in Drug Design & Discovery

Synthesis and Studies of Anticancer and Antimicrobial Activity of New Phenylurenyl Chalcone Derivatives

Abstract

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