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

Akdeniz G. Y., Akgün H., Özakpınar Ö., Duracık M., Öztürk M., İşcan E., ...More

LETTERS IN DRUG DESIGN & DISCOVERY, vol.19, no.6, pp.500-519, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 19 Issue: 6
  • Publication Date: 2022
  • Doi Number: 10.2174/1570180819666220110153542
  • Journal Name: LETTERS IN DRUG DESIGN & DISCOVERY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Biotechnology Research Abstracts, Chemical Abstracts Core, EMBASE
  • Page Numbers: pp.500-519
  • Keywords: Urea, phenylurenyl chalcone, kinase inhibitors, anticancer, antimicrobial, cytotoxicity, TYROSINE KINASE INHIBITORS, UREA DERIVATIVES, ANTIBACTERIAL ACTIVITY, BIOLOGICAL EVALUATION, MOLECULAR DOCKING, DESIGN, CYTOTOXICITY, PREDICTION
  • Marmara University Affiliated: Yes

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-substitutedphenylprop-2-enoyl]phenyl}-N-methylphenyl urea and {4/3-[(2E)-3-substitutedphenylprop-2-enoyl]phenyl}-N-ethylphenyl 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 mu M), 16 (IC50: 5.64 mu M), 19 (IC50: 6.95 mu M) and 34 (IC50: 6.87 mu M) showed good cytotoxic activity on Huh-7 cell line close to Sorafenib (IC50: 4.29 mu M) (as reference). MIC values of compounds 4 and 22 against E. coli were 25 mu g/ml, compounds 3, 14 and 29 against P. aeruginosa 25 mu g/ml, and compounds 11 and 33 against S. aureus 25 mu g/ml. On the other hand, the minimum inhibitory concentration of all tested compounds against C. albicans was 25 mu g/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.