Design, synthesis, and evaluation of 1,2,3‐triazole‐based benzenesulfonamide and flavonol hybrid molecules as anticancer agents

Chen, Y.-C.; Chang, Chuan‐Hsin; Li, Caiwei; Chen, Jih Jung; Shih, Tzenge‐Lien

doi:10.1002/jccs.202300279

J Chinese Chemical Soc

2023

DOI: 10.1002/jccs.202300279

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Design, synthesis, and evaluation of 1,2,3‐triazole‐based benzenesulfonamide and flavonol hybrid molecules as anticancer agents

Y.-C. Chen

Chuan‐Hsin Chang

Caiwei Li

et al.

Abstract: BackgroundThe design and synthesis of hybrid molecules will explore finding new drugs.ObjectivesThe synthesized hybrid molecules to evaluate their biological properties.MethodsApply click chemistry to tether flavonols and benzenesulfonamide.ResultsTwo drug candidates show potential against lung cancer.ConclusionsTwo drug candidates did not affect the normal cells and provided a new drug design route.

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2024

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Cited by 4 publications

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Synthesis of selenophene‐containing flavonols and 2‐styrylchromones: Evaluation of their activities compared with selenophene‐containing chalcones as potential anticancer agents

Chen,

Chang,

Tang

et al. 2024

Archiv der Pharmazie

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Previously, we documented the synthesis and assessed the biological effects of chalcones containing selenium against HT‐29 human colorectal adenocarcinoma cells, demonstrating their significant potential. As research on selenium‐containing flavonoids remains limited, this article outlines our design and synthesis of three selenium‐based flavonols and three 2‐styrylchromones. We conducted evaluations of these compounds to determine their impact on human lung cancer cells (A549, H1975, CL1‐0, and CL1‐5) and their influence on normal lung fibroblast MRC5 cells. Additionally, we included selenium‐based chalcones in our testing for comparative purposes. Our findings highlight that the simplest compound, designated as compound 1, exhibited the most promising performance among the tested molecules.

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Synthesis of selenophene‐containing flavonols and 2‐styrylchromones: Evaluation of their activities compared with selenophene‐containing chalcones as potential anticancer agents

Chen,

Chang,

Tang

et al. 2024

Archiv der Pharmazie

View full text Add to dashboard Cite

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Design and Synthesis of Unsymmetric Benzils, Quinoxalines, and Evaluations of their Anticancer Activities against Human Non‐Small Lung Cancer Cells

Hsu,

Chang

et al. 2024

ChemMedChem

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Quinoxaline and its derivatives exhibit a broad spectrum of biological activity, making them valuable for various therapeutic applications. However, most quinoxalines are synthetically produced due to their scarcity in nature. In this article, a series of unsymmetric benzils were synthesized and subsequently condensed with 1,2‐diaminobenzene to produce unsymmetric quinoxalines. The novel synthetic benzils and quinoxalines were evaluated for their anticancer activities against human non‐small‐cell lung cancer (NSCLC) cells harboring different gene mutations, to explore their potential as anticancer agents. Among these synthesized molecules, compound 5g demonstrated inhibitory effects comparable to those of cisplatin.

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Synthesis, biological evaluation, and computational studies of thiazolyl hydrazone derivatives as triple mutant allosteric EGFR inhibitors

Shinde,

Sarkate,

Rathod

et al. 2024

J Chinese Chemical Soc

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Herein, new thiazole‐2‐yl‐based hydrazone derivatives were synthesized and assessed for in vitro anticancer activity against wild type A549, MCF7, DU145, and mutant H1975 cancer cell lines by 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) assay. Among all, 4‐(4‐Chlorophenyl)‐2‐(2‐((4‐methylthiazol‐5‐yl)methylene)hydrazineyl)thiazole (4b) elicited prominent anticancer activity against wild‐type epidermal growth factor receptor (WT‐EGFR) MCF7 cancer cell line with an IC50 value of 9.57 ± 1.80 μM, whereas 4‐Methyl‐5‐((2‐(4‐(4‐nitrophenyl)thiazol‐2‐yl)hydrazineylidene)methyl)thiazole (4c) showed appreciable activity with an IC50 value of 11 ± 0.7 μM against the mutated EGFR H1975 lung cancer cells. Doxorubicin and Osimertinib were used as the standard drugs for comparison of activity. Compound (4b) significantly increased early apoptosis (30.2%) and late apoptosis (7.6%) at a 5 μM concentration in comparison with the control (early apoptosis 2.5%, late apoptosis 1.2%). The molecular docking study was performed against mutant EGFR (T790M/C797S) (PDB: 5D41) enzyme to gain information about interactions of synthesized molecules with binding pockets. Moreover, ADME study and molecular dynamic simulation studies were accomplished to gain insight into drug‐likeness and conformational stability, respectively. The findings demonstrate a promising alignment between the observed anticancer effects and computational analyses.

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Design, synthesis, and evaluation of 1,2,3‐triazole‐based benzenesulfonamide and flavonol hybrid molecules as anticancer agents

Cited by 4 publications

References 46 publications

Synthesis of selenophene‐containing flavonols and 2‐styrylchromones: Evaluation of their activities compared with selenophene‐containing chalcones as potential anticancer agents

Synthesis of selenophene‐containing flavonols and 2‐styrylchromones: Evaluation of their activities compared with selenophene‐containing chalcones as potential anticancer agents

Design and Synthesis of Unsymmetric Benzils, Quinoxalines, and Evaluations of their Anticancer Activities against Human Non‐Small Lung Cancer Cells

Synthesis, biological evaluation, and computational studies of thiazolyl hydrazone derivatives as triple mutant allosteric EGFR inhibitors

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