N-phenyl-6-chloro-4-hydroxy-2-quinolone-3-carboxamides: Molecular Docking, Synthesis, and Biological Investigation as Anticancer Agents

Sabbah, Dima A.; Haroon, Rawan A.; Bardaweel, Sanaa K.; Hajjo, Rima; Sweidan, Kamal

doi:10.3390/molecules26010073

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N-phenyl-6-chloro-4-hydroxy-2-quinolone-3-carboxamides: Molecular Docking, Synthesis, and Biological Investigation as Anticancer Agents

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Department of Pharmacy, Faculty of Pharmacy, Al-Zaytoonah University of Jordan, Amman 11733, Jordan

Department of Pharmaceutical Sciences, School of Pharmacy, The University of Jordan, Amman 11942, Jordan

Department of Chemistry, The University of Jordan, Amman 11942, Jordan

Author to whom correspondence should be addressed.

Academic Editor: Isabelle Mus-Veteau

Molecules 2021, 26(1), 73; https://doi.org/10.3390/molecules26010073

Received: 30 November 2020 / Revised: 18 December 2020 / Accepted: 23 December 2020 / Published: 25 December 2020

(This article belongs to the Collection Novel Approaches of Anticancer Therapy)

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Abstract

Cancer is a multifactorial disease and the second leading cause of death worldwide. Diverse factors induce carcinogenesis, such as diet, smoking, radiation, and genetic defects. The phosphatidylinositol 3-kinase (PI3Kα) has emerged as an attractive target for anticancer drug design. Eighteen derivatives of N-phenyl-6-chloro-4-hydroxy-2-quinolone-3-carboxamide were synthesized and characterized using FT-IR, NMR (¹H and ¹³C), and high-resolution mass spectra (HRMS). The series exhibited distinct antiproliferative activity (IC₅₀ µM) against human epithelial colorectal adenocarcinoma (Caco-2) and colon carcinoma (HCT-116) cell lines, respectively: compounds 16 (37.4, 8.9 µM), 18 (50.9, 3.3 µM), 19 (17.0, 5.3 µM), and 21 (18.9, 4.9 µM). The induced-fit docking (IFD) studies against PI3Kαs showed that the derivatives occupy the PI3Kα binding site and engage with key binding residues. View Full-Text

Keywords: anticancer; colon cancer; PI3Kα; AKT; docking; quinolone-3-carboxamide

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MDPI and ACS Style

Sabbah, D.A.; Haroon, R.A.; Bardaweel, S.K.; Hajjo, R.; Sweidan, K. N-phenyl-6-chloro-4-hydroxy-2-quinolone-3-carboxamides: Molecular Docking, Synthesis, and Biological Investigation as Anticancer Agents. Molecules 2021, 26, 73. https://doi.org/10.3390/molecules26010073

AMA Style

Sabbah DA, Haroon RA, Bardaweel SK, Hajjo R, Sweidan K. N-phenyl-6-chloro-4-hydroxy-2-quinolone-3-carboxamides: Molecular Docking, Synthesis, and Biological Investigation as Anticancer Agents. Molecules. 2021; 26(1):73. https://doi.org/10.3390/molecules26010073

Chicago/Turabian Style

Sabbah, Dima A., Rawan A. Haroon, Sanaa K. Bardaweel, Rima Hajjo, and Kamal Sweidan. 2021. "N-phenyl-6-chloro-4-hydroxy-2-quinolone-3-carboxamides: Molecular Docking, Synthesis, and Biological Investigation as Anticancer Agents" Molecules 26, no. 1: 73. https://doi.org/10.3390/molecules26010073

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N-phenyl-6-chloro-4-hydroxy-2-quinolone-3-carboxamides: Molecular Docking, Synthesis, and Biological Investigation as Anticancer Agents

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