(E)-4-(3-(3-(4-Methoxyphenyl)acryloyl)phenoxy)butyl 2-Hydroxybenzoate

Ihsan Ikhtiarudin,Noval Herfindo,Rahayu Utami,Emma Susanti,Adel Zamri,Nesa Agistia,Neni Frimayanti,Nurmaida Nurmaida,Mentari Mentari,Rahma Dona

doi:10.3390/m1195

Abstract

A new hybrid compound of chalcone-salicylate (title compound) has been successfully synthesized using a linker mode approach under reflux condition. The structure of the title compound has been established by spectroscopic analysis including UV-Vis, FT-IR, HRMS, 1D, and 2D NMR. Then, computational approach was also applied in this study through molecular docking and MD simulation to explore its potency against breast cancer. The results of the molecular docking study showed that the title compound exhibited more negative value of binding free energy (−8.15 kcal/mol) than tamoxifen (−7.00 kcal/mol). In addition, no striking change in the positioning of the interacting residues was recorded before and after the MD simulations. Based on the studies, it can be predicted that the title compound has a cytotoxic activity potency against breast cancer through ERα inhibition and it presumably can be developed as anticancer agent candidate.

Highlights

Chalcones (1,3-diphenyl-prop-2-en-1-ones) are natural products that are found in several plant species and they have been reported for broad spectrum of biological activities.Their analogues and derivatives have been widely synthesized to explore their potential uses [1,2,3], especially in anticancer drug discovery researches [4]
We report the synthesis of a new hybrid compound, (E)-4-(3-(3-(4methoxyphenyl)acryloyl)phenoxy)butyl 2-hydroxybenzoate using a more molecules that are expected to have a better biological activity than their parent
We report the synthesis of a new hybrid compound, (E)-4-(3-(3-(4-methoxyphenyl)acryloyl)phenoxy)butyl 2-hydroxybenzoate using a linker mode approach

Summary

Introduction

Chalcones (1,3-diphenyl-prop-2-en-1-ones) are natural products that are found in several plant species and they have been reported for broad spectrum of biological activities. Their analogues and derivatives have been widely synthesized to explore their potential uses [1,2,3], especially in anticancer drug discovery researches [4]. Some researchers have reported that several hydroxylated and methoxylated chalcones exhibited potent cytotoxic activity against the MCF-7 cell line [4,5]. Some salicylic acid derivatives have been reported as potent cytotoxic agents against several cancer cell lines, including MCF-7 [6]. Some workers have reported that this approach has been proven to be an effective way to develop new multifunctional compounds from hybridization or conjugation of two or more molecules that are expected to have a better biological activity than their parent compounds [9]

Methods

Results

Conclusion