Heteroaromatization of Coumarin Part III: One-pot Synthesis, Antitumor Activity, DFT Studies, and Molecular Docking of Coumarin Derivatives-Reference-Cited by-同舟云学术

Heteroaromatization of Coumarin Part III: One-pot Synthesis, Antitumor Activity, DFT Studies, and Molecular Docking of Coumarin Derivatives

Published:2025-01 Issue:1 Volume:29 Page:75-83
ISSN:1385-2728
Container-title:Current Organic Chemistry
language:en
Short-container-title:COC

Author:

Alamri Abdullah A.¹,Borik Rita M.A.¹,Abd El-Wahab Ashraf H.F.¹,Al-Dies Al-Anood M.²,Mohamed Hany M.¹,Ibrahim Diaa A.³

Affiliation:

1. Department of Physical Sciences, Chemistry Division, College of Sciences, Jazan University, P.O. Box. 114, Jazan 45142, Kingdom of Saudi Arabia

2. Department of Chemistry, Umm Al-Qura University, Al-Qunfudah University College, 21912, Al-Qunfudah, Kingdom of Saudi Arabia

3. Department of Chemistry, College of Science, Jazan University, B.O. Box114, 45142, Jazan, Kingdom of Saudi Arabia

Abstract

A one-pot three/two-component reaction of 3-acetyl-coumarin (1), 4/3- anisaldehyde (2a,b) and malononitrile or 3-acetylcoumarin (1) and 2-(4/3- methoxybenzylidene)malononitrile (5a,b) in glacial acetic acid/ammonium acetate under reflux afforded 2-amino-4-(4/3-methoxyphenyl)-6-(2-oxo-2H-chromen-3-yl)nicotinonitrile (4a,b). Spectral data helped establish the structures of the compounds. Subsequently, an antiproliferative evaluation against a selected line of tumorous cells (HepG-2, MDA-MB- 231 and A549) was performed in-vitro for the novel 2-amino-4-(4/3-methoxyphenyl)-6-(2- oxo-2H-chromen-3-yl)nicotinonitrile (4a,b). Compound 4a exhibited good efficiency against the MDA-MB-231 and A549 cell lines compared with the reference drug (Vinblastine). Furthermore, the chemical reactivity of both compounds was discussed using DFT. Lastly, a molecular docking analysis was addressed and conducted for these desired molecules.

Publisher

Bentham Science Publishers Ltd.