Synthesis of novel xanthone and acridone carboxamides with potent antiproliferative activities

Georgakopoulos, Antonios; Kalampaliki, Amalia D.; Gioti, Katerina; Hamdoun, Sami; Giannopoulou, Aikaterini F.; Efferth, Thomas; Stravopodis, Dimitrios J.; Τέντα, Ρωξάνη; Marakos, Panagiotis; Pouli, Nicole; Kostakis, Ioannis K.

doi:10.1016/j.arabjc.2020.09.025

Cited by 4 publications

(3 citation statements)

References 49 publications

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“…Molecular hybridization of chalcone with other structures, such as benzimidazole and carbazole, as well as molecular hybridization of xanthone with pyran, cinnamate, and acridone carboxamides, have been reported. It was found that the hybrid compounds gave stronger anticancer and antiproliferative activities than the individual structures, revealing a synergistic effect on molecular hybridization due to multiple non-covalent interactions that could be made with the cancer cells' receptors [35][36][37][38][39]. In light of the above findings, a molecular hybridization of xanthone and chalcone could yield novel anticancer agents to be developed in the future.…”

Section: ■ Introductionmentioning

confidence: 93%

Molecular Docking and Molecular Dynamic Investigations of Xanthone-Chalcone Derivatives against Epidermal Growth Factor Receptor for Preliminary Discovery of Novel Anticancer Agent

Kurniawan,

Yudha,

Nugraha

et al. 2024

Indones. J. Chem.

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Epidermal growth factor receptor (EGFR) is found to be overexpressed in cancer cells as it controls angiogenesis, cell signaling, and proliferation mechanisms. Therefore, EGFR has been known as a common target for the initial screening of new anticancer agents. Either xanthone or chalcone has been evaluated as the anticancer agents, and their activity strongly depends on the type and position of the attached functional group. Therefore, molecular hybridization between xanthone and chalcone could yield novel anticancer agents through the EGFR inhibition mechanism. Herein, a series of xanthone-chalcone derivatives with hydrogen-bond-acceptor or hydrogen-bond-donor substituents at ortho, meta, and para positions was evaluated as the EGFR inhibitor. Thirty-seven xanthone-chalcones were designed and docked in the active site of EGFR. Compared to the native ligand, pristine xanthone-chalcone gave a 1.215× stronger binding energy and a 13.97× lower binding constant. Compound 3SH was found to be the most promising candidate due to its strongest binding energy (−9.71 kcal/mol) and the lowest binding constant (0.08 µM). Furthermore, molecular dynamic studies demonstrated that complex EGFR-3SH was stable for 100 ns simulation. These in silico investigations show that the xanthone-chalcone derivative is a promising novel anticancer agent to be examined through in vitro and in vivo assays.

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Section: ■ Introductionmentioning

confidence: 93%

Molecular Docking and Molecular Dynamic Investigations of Xanthone-Chalcone Derivatives against Epidermal Growth Factor Receptor for Preliminary Discovery of Novel Anticancer Agent

Kurniawan,

Yudha,

Nugraha

et al. 2024

Indones. J. Chem.

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“…Interestingly, the reaction of chloride 13 with potassium acetate in methanol gave compound 27 upon intramolecular cyclisation. Reaction of these amides with the suitable amines resulted in the target amino-substituted compounds 17-20 (Scheme 2) [25]. The methoxy compounds 17 and 18 were then efficiently demethoxylated upon treatment with BBr3 to provide the phenol analogs 21 and 22, respectively.…”

Section: Chemistrymentioning

confidence: 99%

“…1 H NMR (600 MHz, CDCl 3 -MeOD) δ (ppm) 8.80 (dd, J = 7.9, 1.4 Hz, 1H, H-7), 8.45 (dd, J = 8.3, 1.7 Hz, 1H, H-6 ), 8.01 (dd, J = 8.0, 1.4 Hz, 1H, H-5), 7.55-7.50 (m, 2H, H-6, H-4 ), 7.13-7.11 (m, 2H, H-3 , H-5 ), 3.31 (s, 2H, CH 2 ), 2.62 (s, 6H, (CH 3 ) 2 ). 13 (25). To a solution of 13 (100 mg, 0.29 mmol) in anh.…”

Section: Synthesis Of Compounds 3-37mentioning

confidence: 99%

Synthesis and Biological Evaluation of 2-Substituted Quinazolin-4(3H)-Ones with Antiproliferative Activities

Karelou,

Kampasis,

Kalampaliki

et al. 2023

Molecules

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Sixteen new 2-substituted quinazolines were synthesized using a straightforward methodology starting from 2-methoxybezoic acid or 3-methoxy-2-naphthoic acid. The anti-proliferative activity of the target compounds was evaluated against nine cancer cell lines. Additionally, all the compounds were screened for their potency and selectivity against a panel of 109 kinases and four bromodomains, using Differential Scanning Fluorimetry (DSF). Compound 17 bearing a 2-methoxyphenyl substitution along with a basic side chain displayed a remarkable profile against the majority of the tested cell lines.

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A comprehensive review on acridone based derivatives as future anti-cancer agents and their structure activity relationships

Yadav

Murahari

Peters

et al. 2022

European Journal of Medicinal Chemistry

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Synthesis of novel xanthone and acridone carboxamides with potent antiproliferative activities

Cited by 4 publications

References 49 publications

Molecular Docking and Molecular Dynamic Investigations of Xanthone-Chalcone Derivatives against Epidermal Growth Factor Receptor for Preliminary Discovery of Novel Anticancer Agent

Molecular Docking and Molecular Dynamic Investigations of Xanthone-Chalcone Derivatives against Epidermal Growth Factor Receptor for Preliminary Discovery of Novel Anticancer Agent

Synthesis and Biological Evaluation of 2-Substituted Quinazolin-4(3H)-Ones with Antiproliferative Activities

A comprehensive review on acridone based derivatives as future anti-cancer agents and their structure activity relationships

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