Chemosensing Properties of Coumarin Derivatives: Promising Agents with Diverse Pharmacological Properties, Docking and DFT Investigation

Sadeq M Al-Hazmy; Mohamed Oussama Zouaghi; Jamal N Al-Johani; Youssef Arfaoui; Rania Al-Ashwal; Bechir Hammami; Ibrahim A Alhagri; Nabil A Alhemiary; Naceur Hamdi

doi:10.3390/molecules27185921

Chemosensing Properties of Coumarin Derivatives: Promising Agents with Diverse Pharmacological Properties, Docking and DFT Investigation

Molecules. 2022 Sep 12;27(18):5921. doi: 10.3390/molecules27185921.

Authors

Sadeq M Al-Hazmy^{1

2}, Mohamed Oussama Zouaghi³, Jamal N Al-Johani¹, Youssef Arfaoui³, Rania Al-Ashwal^{4

5}, Bechir Hammami¹, Ibrahim A Alhagri¹, Nabil A Alhemiary^{6

7}, Naceur Hamdi^{8

9}

Affiliations

¹ Department of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi Arabia.
² Department of Chemistry, College of Science, Sana'a University, Sana'a P.O. Box 1247, Yemen.
³ Laboratory of Characterizations, Applications & Modeling of Materials (LR18ES08), Department of Chemistry, Faculty of Sciences, University of Tunis El Manar, Tunis 2092, Tunisia.
⁴ School of Biomedical Engineering and Health Sciences, Faculty of Engineering, Universiti Teknologi Malaysia, Johor Bahru 81310, Malaysia.
⁵ Advanced Diagnostic and Progressive Human Care Research Group, School of Biomedical Engineering and Health Science Teknologi Malaysia, Johor Bahru 81310, Malaysia.
⁶ Department of Chemistry, College of Science, Ibb University, Ibb P.O. Box 70270, Yemen.
⁷ Department of Chemistry, College of Science and Arts at Sharurah, Najran University, P.O. Box 1988, Najran 11001, Saudi Arabia.
⁸ Department of Chemistry, College of Science and Arts at Ar Rass, Qassim University, P.O. Box 53, Ar Rass 51921, Saudi Arabia.
⁹ Research Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif 1054, Tunisia.

Abstract

In this work, a three-component reaction of 3-acetyl-4-hydroxycoumarine, malononitrile, or cyanoacetate in the presence of ammonium acetate was used to form coumarin derivatives. The chemical structures of new compounds were identified by ¹H, ¹³C NMR and an elemental analysis. These compounds were examined in vitro for their antimicrobial activity against a panel of bacterial strains. In addition, these compounds were investigated for antioxidant activities by superoxideradical, DPPH (2,2-Diphenyl-1-picrylhydrazyl), and hydroxyl radical scavenging assays, in which most of them displayed significant antioxidant activities. Furthermore, these compounds were evaluated for anti-inflammatory activity by indirect hemolytic and lipoxygenase inhibition assays and revealed good activity. In addition, screening of the selected compounds 2-4 against colon carcinoma cell lines (HCT-116) and hepatocellular carcinoma cell lines (HepG-2) showed that that 2-amino-4-hydroxy-6-(4-hydroxy-2-oxo-2H-chromen-3-yl)nicotinonitrile 4 exhibited good cytotoxic activity against standard Vinblastine, while the other compounds exhibited moderate cytotoxic activity. Docking simulation showed that2-amino-4-hydroxy-6-(4-hydroxy-2-oxo-2H-chromen-3-yl)nicotinonitrile 4 is an effective inhibitor of the tumor protein HCT-116. A large fluorescence enhancement in a highly acidic medium was observed, and large fluorescence quenching by the addition of traces of Cu²⁺ and Ni²⁺ was also remarked.

Keywords: DFT investigation; anti-inflammatory; antibacterial; antioxidant; antiproliferative; chemosensor; coumarin; docking simulation; fluorescence; quantum yield; quenching.

MeSH terms

Anti-Infective Agents*
Antineoplastic Agents* / chemistry
Antineoplastic Agents* / pharmacology
Antioxidants / chemistry
Antioxidants / pharmacology
Coumarins / chemistry
Coumarins / pharmacology
Hydroxyl Radical
Lipoxygenases
Molecular Docking Simulation
Vinblastine

Substances

Anti-Infective Agents
Antineoplastic Agents
Antioxidants
Coumarins
Hydroxyl Radical
Vinblastine
Lipoxygenases

Grants and funding

Deputyship for Research & Innovation, Ministry of Education, Saudi Arabia for funding this research work through the project number (QU-IF-2-5-4-25827).