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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Research Article

Design, Synthesis, Molecular Docking and Cytotoxicity of Stilbene-arylcinnamide Hybrids on A549 Lung Cancer Cells

Author(s): Nurain Syazwani Mohd. Zaki, Nik Nur Syazni Nik Mohamad Kamal, Unang Supratman, Desi Harneti, Mohd. Zaheen Hassan and Mohamad Nurul Azmi Mohamad Taib*

Volume 27, Issue 16, 2023

Published on: 18 October, 2023

Page: [1458 - 1470] Pages: 13

DOI: 10.2174/0113852728267280231010065610

Price: $65

Abstract

A new series of stilbene-arylcinnamide hybrids have been designed and synthesized with various substituents. These compounds were characterized by FTIR, 1D- and 2D-NMR as well as mass spectroscopy analysis (HRESIMS). The synthesized compounds were tested for their cytotoxic activity against human lung cancer A549 cell. The most active compound was further studied via in silico molecular docking on α,β- interface of tubulin. Total 18 new stilbene-arylcinnamide hybrids have been synthesized with 42-80% yield and evaluated for their cytotoxic activity against human lung cancer A549 cell. Particularly, compound 6b exhibited potent cytotoxicity against A549 cells with the IC50 value of 19.9 μM. In addition, compound 7b displayed moderate activities with the IC50 value of 33.9 μM, while other hybrids were considered inactive. Structural activity relationship (SAR) studies revealed that the presence of an isopropyl group at the para position on ring A and a methyl group at the para position on ring C is beneficial for enhanced cytotoxicity. Furthermore, we also developed an in silico molecular docking to study the binding interaction of the active compounds to the α,β-interface of tubulin (PDB ID: 3E22). Hybrids 6b and 7b demonstrated promising binding interactions and affinities into the tubulin active site with calculated binding energy of -7.2 and -8.0 kcal/mol, respectively.

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