Coumarin hybrids: a sighting of their roles in drug targeting

Zeki, Nameer Mazin; Mustafa, Yasser Fakri

doi:10.1007/s11696-024-03498-z

Cited by 5 publications

(1 citation statement)

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“…Based on the previous studies describing the inhibition of monoamine oxidase and cholinesterase exerted by indazoles [ 37 ], 1,2,3-triazole–coumarin hybrids [ 38 , 39 , 40 ], and arylsulfonamides [ 41 , 42 ], this research aims to contribute to the development of novel molecule conjugates by exploring the linkage of a coumarin bearing a nitro group to sulfonamide and indazole, through simple and efficient synthetic routes, such as reduction, coupling reactions, and a copper-azide-alkyne-cycloaddition (CuAAC) methodology in order to prepare and evaluate the potential of new hybrids as neuroprotective agents. The drug design derives from previous studies with coumarins and related compounds (e.g., benzodioxine), which have revealed marked anti-inflammatory properties [ 43 , 44 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Electron Density Theory Study, Molecular Docking, and Pharmacological Evaluation of New Coumarin–Sulfonamide–Nitroindazolyl–Triazole Hybrids as Monoamine Oxidase Inhibitors

Eddahmi,

La Spada,

Domingo

et al. 2024

IJMS

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Inhibitors of monoamine oxidases (MAOs) are of interest for the treatment of neurodegenerative disorders and other human pathologies. In this frame, the present work describes different synthetic strategies to obtain MAO inhibitors via the coupling of the aminocoumarin core with arylsulfonyl chlorides followed by copper azide-alkyne cycloaddition, leading to coumarin–sulfonamide–nitroindazolyl–triazole hybrids. The nitration position on the coumarin moiety was confirmed through nuclear magnetic resonance spectroscopy and molecular electron density theory in order to elucidate the molecular mechanism and selectivity of the electrophilic aromatic substitution reaction. The coumarin derivatives were evaluated for their inhibitory potency against monoamine oxidases and cholinesterases. Molecular docking calculations provided a rational binding mode of the best compounds in the series with MAO A and B. The work identified hybrids 14a–c as novel MAO inhibitors, with a selective action against isoform B, of potential interest to combat neurological diseases.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Electron Density Theory Study, Molecular Docking, and Pharmacological Evaluation of New Coumarin–Sulfonamide–Nitroindazolyl–Triazole Hybrids as Monoamine Oxidase Inhibitors

Eddahmi,

La Spada,

Domingo

et al. 2024

IJMS

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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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Linearly ring-fused coumarins: A review of their cancer-fighting attributes

Jibroo,

Mustafa

2024

Results in Chemistry

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Coumarin hybrids: a sighting of their roles in drug targeting

Cited by 5 publications

References 100 publications

Synthesis, Molecular Electron Density Theory Study, Molecular Docking, and Pharmacological Evaluation of New Coumarin–Sulfonamide–Nitroindazolyl–Triazole Hybrids as Monoamine Oxidase Inhibitors

Synthesis, Molecular Electron Density Theory Study, Molecular Docking, and Pharmacological Evaluation of New Coumarin–Sulfonamide–Nitroindazolyl–Triazole Hybrids as Monoamine Oxidase Inhibitors

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

Linearly ring-fused coumarins: A review of their cancer-fighting attributes

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