1,2,3-triazole clubbed and dichloro substituted novel aurones as potential anticancer agents targeting digestive enzymes: Design, synthesis, DFT, ADME and molecular docking studies

Kumar, Gourav; Saroha, Bhavna; Arya, Priyanka; Ghosh, Sushmita; Kumari, Bavita; Nassare, Vilas D.; Raghav, Neera; Kumar, Suresh

doi:10.1016/j.molstruc.2024.139460

Journal of Molecular Structure

2025

DOI: 10.1016/j.molstruc.2024.139460

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1,2,3-triazole clubbed and dichloro substituted novel aurones as potential anticancer agents targeting digestive enzymes: Design, synthesis, DFT, ADME and molecular docking studies

Gourav Kumar,

Bhavna Saroha,

Priyanka Arya

et al.

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Cited by 3 publications

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Design and Synthesis of Propargyloxy Functionalized Pyrazole‐Based Aurones: Exploring Their Potent Anticancer Properties Against AGS and MCF‐7 Cell Lines

Lathwal,

Kumar,

Sharma

et al. 2024

Chemistry & Biodiversity

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FDA‐approved numerous commercial and natural drugs used in cancer treatment feature either pyrazole or alkyne moieties. Based on this, we designed and synthesized twenty novel propargyloxy‐substituted pyrazole‐based aurones (10a‐j and 11a‐j) and evaluated for their anticancer potential against cancerous MCF‐7 and AGS cell lines, as well as normal cell line HEK‐293, through MTT assay. Among these tested compounds, five (10d‐f, 11e, and 11f) displayed potent cytotoxic properties for AGS cancer cell line with IC50 values ranging from 19.7 µM ‐ 28.5 µM, better than the reference drugs Leucovorin (IC50 = 30.8 µM) and Oxaliplatin (IC50 = 29.8 µM). Furthermore, compounds 10b, 10c 11a, 11c, and 11d demonstrated a significant cytotoxic potential against the MCF‐7 cancer cell line with a single‐digit micromolar IC50 potency (4.8 µM – 8.5 µM) compared to the standard drug Paclitaxel (IC50 = 19.7 µM). The cytotoxic studies of above selected potent active hybrid compounds, against HEK‐293 (human embryonic kidney 293), normal cell line, further highlight the potential use of 10c molecule (IC50 = 4.8 μM against MCF‐7 cells) as an anti‐cancer agent for breast cancer with a selectivity index of 2.597. The cytotoxic results were further supported by the molecular docking studies.

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Design and Synthesis of Propargyloxy Functionalized Pyrazole‐Based Aurones: Exploring Their Potent Anticancer Properties Against AGS and MCF‐7 Cell Lines

Lathwal,

Kumar,

Sharma

et al. 2024

Chemistry & Biodiversity

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1,2,3‐Triazole‐Based New Aurones as Anticancer Agents with the Capability to Target Extracellular Digestive Enzymes

Kumar,

Saroha,

Kumar

et al. 2024

ChemistrySelect

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This study involves the synthesis of a series of dimethyl substituted novel aurones, featuring 1,2,3‐triazole as an integral structure. All the newly synthesized compounds were thoroughly characterized using various spectroscopic tools and also subjected to computational analysis utilizing the DFT/B3LYP methodology, which involved the determination of frontier molecular orbital energy values and the computation of various quantum chemical parameters. Further their impact on cell viability and cytotoxic activity on the adenocarcinoma gastric cell line (AGS) was investigated using cell‐based MTT assay. Compounds 6d, 6o and 6p displayed significant cytotoxic activity, reducing cell viability to a greater extent with IC50 values of 9.74, 20.09, and 5.92 µM, respectively and even better than the standard chemotherapeutic drug leucovorin (IC50 = 30.8 µM). In addition, all the compounds were also screened for their extracellular enzymatic assay and through in vitro results compound 6n emerged as the efficient inhibitor of amylase (% inhibition = 51.92) and trypsin (% inhibition = 68.36), whereas an activation is observed for lipase (% activation = 269.48). In silico molecular docking was also conducted to assess the interactions between proteins and ligands, revealing the binding patterns of the synthesized compounds and the standard drug with receptor proteins.

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Unlocking the Anticancer potential of 6-propargyloxyaurone against AGS cancer cell line: Design, Synthesis, SAR, DFT, Hirshfeld Surface and Molecular Docking Analysis

Kumar,

Bishnoi,

Kumar

et al. 2024

Journal of Molecular Structure

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1,2,3-triazole clubbed and dichloro substituted novel aurones as potential anticancer agents targeting digestive enzymes: Design, synthesis, DFT, ADME and molecular docking studies

Cited by 3 publications

References 61 publications

Design and Synthesis of Propargyloxy Functionalized Pyrazole‐Based Aurones: Exploring Their Potent Anticancer Properties Against AGS and MCF‐7 Cell Lines

Design and Synthesis of Propargyloxy Functionalized Pyrazole‐Based Aurones: Exploring Their Potent Anticancer Properties Against AGS and MCF‐7 Cell Lines

1,2,3‐Triazole‐Based New Aurones as Anticancer Agents with the Capability to Target Extracellular Digestive Enzymes

Unlocking the Anticancer potential of 6-propargyloxyaurone against AGS cancer cell line: Design, Synthesis, SAR, DFT, Hirshfeld Surface and Molecular Docking Analysis

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