Synthesis of (E)-7-arylidene-5-(hydroxy(aryl)methyl)bicyclo[3.2.0] heptan-6-one derivatives as anti-cancer agents

Year 2023, Volume: 12 Issue: 3, 149 - 156, 31.12.2023

Mustafa Ceylan , Bahar Zorlu , Ayşe Şahin Yağlıoğlu , Nuray Akdoğan Üremiş , Meliha Burcu Gürdere , Meryem Keçeci Sarıkaya , Yakup Budak

https://doi.org/10.54187/jnrs.1366848

Abstract

7,7-Dichlorobicyclo [3.2.0]heptan-6-one was prepared by adding dichloroketene to cyclopentene. Reduction of 7,7-dichlorobicyclo[3.2.0]heptan-6-one with Zn in acetic acid afforded the bicyclo[3.2.0]heptan-6-one. (E)-7-Arylidene-5-(hydroxy(aryl)methyl)bicyclo [3.2.0]heptan-6-ones were synthesized by addition of related benzaldehydes to bicyclo[3.2.0]heptan-6-one. The anti-proliferative activities of synthesized compounds were elucidated against rat brain tumor (C6) and human cervical carcinoma cells (HeLa) cell lines. The most active compound was chloro derivative against C6 cell lines with IC50 = 2.45 μM value (5-FU, IC50 = 14.82 μM). Moreover, the most active compound was methyl derivative against HeLa cell lines with IC50 = 26.30 μM (5-FU, IC50 = 29.30 μM).

Keywords

α, β-Unsaturated ketones, Anti-proliferative activity, C6, HeLa, 5-Fu

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