Synthesis and anticancer activity of novel Eugenol derivatives against breast cancer cells

Abstract

Eugenol chemically known as 4-allyl-2-methoxyphenol is a major phenolic component of Syzigium aromaticum and associated with significant biological activities. In the present work, new eugenol 1,2,3-triazole derivatives have been synthesized, characterized using NMR, mass spectrometry, IR, and elemental analysis and screened for their anticancer activity against breast cancer cells. Compound 9, namely 3-(4-((4-allyl-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N'-(4-methylbenzoyl) benzohydrazide was found to be the most potent candidate and better than eugenol in exhibiting cytotoxicity with IC₅₀ 6.91 and 3.15 μM, comparable to Doxorubicin with IC₅₀ 6.58 and 3.21 μM against MDA-MB-231 and MCF-7 cells, respectively. Furthermore, compound 9 treated MCF-7 cells as observed by propidium iodide staining significantly increased cell population of S phase and G2 phase to 43.64% and 35.19%, respectively therefore arresting cell cycle at G2 and S phase. These results indicate that eugenol linked 1,2,3-triazole ring could be used as anticancer leads for the treatment of this deadly diseases.

Graphical Abstract

Keywords:

• eugenol
• 1,2,3-triazole
• cytotoxicity
• cell cycle

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was financially supported by the Deanship of Scientific Research (Project No. 116/1438), Al- Baha university, Al Baha, Kingdom of Saudi Arabia for funding the project.