Coumarins: Chemical Synthesis, Properties and Applications

Düzce Üniversitesi Bilim ve Teknoloji Dergisi, Journal Year: 2025, Volume and Issue: 13(1), P. 131 - 170

Published: Jan. 30, 2025

Coumarins are compounds characterized by a benzopyrone structure resulting from the condensation of pyrone and benzene ring. They commonly found as secondary metabolites in various plants, microorganisms, sponges. These play crucial role defence mechanisms, extensive research has revealed numerous biological activities associated with these compounds. Coumarin its derivatives show significant potential candidates for new drugs due to their exceptional biocompatibility wide range activities, including antimicrobial, anticancer, antimitotic, antioxidant, anti-inflammatory, anticoagulant properties. Beyond medicinal applications, simple versatile scaffold structures coumarins have use fields such food production, agriculture, cosmetics, textiles. This review covers classification coumarin derivatives, well chemical synthesis methods. Furthermore, it delves into properties, diverse application areas coumarins.

Language: Английский

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Systematic Analysis of the Chemical Components of Gentiana urnula Harry Sm Using SIRIUS and Liquid Chromatography High‐Resolution Mass Spectrometry

Rapid Communications in Mass Spectrometry, Journal Year: 2025, Volume and Issue: 39(9)

Published: Feb. 17, 2025

ABSTRACT Rationale Gentiana urnula Harry Sm is a frequently utilized traditional Chinese medicine (TCM) with applications in the treatment of range ailments including jaundice, gastrointestinal ulcers, and influenza. Despite its widespread uses, there lack comprehensive researches on chemical composition. Methods This study integrated SIRIUS, quantitative structure‐retention relationship (QSRR), liquid chromatography high‐resolution mass spectrometry (LC‐HRMS) to identify compounds Sm. Results A total 213 were identified high confidence based retention time (t R ), MS 1 , MS/MS. Among compounds, 26 positively firstly More than 5000 classified Spatial distribution revealed similarities compound between roots stems, while differences observed leaves flowers. Conclusions lays foundation for further investigations into biological activity pharmacological mechanism

Language: Английский

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Synthesis, Computational, and Photophysical Probing Interactions of Novel Isatin‐Incorporated Thiazolyl‐Coumarins as Potent Antitubercular Agents

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(10)

Published: March 1, 2025

Abstract In this work, we reported the synthesis of a novel series isatin‐incorporated thiazolyl‐coumarin derivatives 4(a–h) by one‐pot three‐component reaction substituted isatin, thiosemicarbazide, and 3‐(2‐bromoacetyl) coumarin. The structures coumarin‐thiazole scaffolds were precisely established their IR, NMR, HRMS spectral data. UV–Vis absorption study target molecules was investigated in six different solvents. Geometrical optimization, molecular electrostatic potential regions, quantum chemical parameters assessed using density functional theory (DFT) to explore electronic properties derivatives. synthesized compounds screened for vitro antimycobacterial activity against Mycobacterium tuberculosis ; all exhibited excellent antitubercular efficacy with MIC ≤ 3.25 µg/mL; among them, 4c 4f most potent 1.56 µg/mL. Furthermore, silico docking analyses enoyl‐ACP reductase (InhA) enzyme conducted; ligands demonstrated favorable binding interactions within active site InhA enzyme.

Language: Английский

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One-pot synthesis, anticancer, EGFR and caspases assays of novel fused [1,2,3]triazolo-pyrrolo[2,1-b]quinazolinones

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1320, P. 139570 - 139570

Published: Aug. 9, 2024

Language: Английский

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Synthesis, characterization, anticancer activity, molecular docking and DFT calculation of 3-acetylcoumarin thiosemicarbazones and Schiff’s bases

Results in Chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 101794 - 101794

Published: Sept. 1, 2024

Language: Английский

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Novel coumarin-thiazolidine-2,4-dione hybrids as potential α-glucosidase inhibitors: Synthesis and bioactivity evaluation

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: unknown, P. 140481 - 140481

Published: Oct. 1, 2024

Language: Английский

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Structural characterization, theoretical, and antibacterial activity study of halogen-η3-allylpalladium(II) complexes incorporating 2-, 3- and 4-pyridyl-methylen-4-methylumbelliferone esters

Polyhedron, Journal Year: 2025, Volume and Issue: unknown, P. 117414 - 117414

Published: Jan. 1, 2025

Language: Английский

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Meta-, Regioselective Amination of Cyclic Diaryliodoniums through C–I and C–O Bond Cleavages: An Access to Functionalized Coumarins

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 26, 2025

Despite the widespread ortho-functionalization of cyclic diaryliodoniums in organic chemistry, corresponding meta-functionalization is less explored. Herein, we report a practical meta-selective activation hypervalent iodoniums for synthesis 4-amino coumarin derivatives broad functional group tolerance and environmentally friendly manner. The practicability this protocol was further highlighted by late-stage modification some common pharmaceuticals natural products.

Language: Английский

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Two-Step Tandem Synthesis of Coumarin Derivatives Containing Bioamide Skeleton Catalyzed by Lipozyme TL IM from Thermomyces lanuginosus in Sustainable Continuous-Flow Microreactors

Catalysts, Journal Year: 2025, Volume and Issue: 15(3), P. 268 - 268

Published: March 12, 2025

Due to their remarkable biological and pharmacological activities such as antibacterial, antifungal, anticoagulant, antioxidant, anticancer, anti-inflammatory properties, synthesis of coumarins derivatives has attracted considerable attention in research development among both organic medicinal chemists. In this paper, we demonstrated for the first time a two-step tandem enzymatic coumarin bioamide through sustainable continuous-flow technology. Salicylaldehyde dimethyl malonate were firstly reacted obtain carboxylate methyl derivatives, which then with various biogenic amines at 50 °C about 40 min under catalysis lipase TL IM from Thermomyces lanuginosus reactors. Reaction parameters reaction solvent, catalyst type, reactant ratio, residence time, temperature comparative experiments traditional batch process studied. Ideal product yields (62.7–87.1%) obtained. Environmentally friendly methanol was applied medium. Substantially shorter times well significant increase yield obtained compared process. This innovative approach provides promising green, efficient rapid strategy pharmaceutical further on novel derivatives.

Language: Английский

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Synthesis and Biological Evaluation of Some Coumarin–Triazole Conjugates as Potential Anticancer Agents

Scientia Pharmaceutica, Journal Year: 2025, Volume and Issue: 93(2), P. 16 - 16

Published: March 31, 2025

Despite the discovery of many chemotherapeutic drugs that prevent uncontrolled cell division processes, development compounds with higher anticancer efficacy and a lower level side effects is an important task in modern pharmaceutical chemistry. Herein, mild convenient method for preparation N1-substituted 3-(1,2,3-triazolyl-methoxycarbonyl)coumarins or bis(coumarine-3-carboxylate)bis(triazole)alkandiyl by copper(I)-catalyzed Huisgen cycloaddition reaction readily available coumarin-3-carboxylic acid propynyl ester azides diazides has been presented. The synthesized have tested their cytotoxicity on various cancer noncancerous lines using MTT assay. All new were nontoxic normal epithelial VERO cells. Two derivatives exhibited selectivity towards HPV-negative human cervical cells, C33 A, excellent activities low concentrations (GI50 4.4–7.0 µM). In vitro mechanistic studies showed bis(coumarine)bis(triazolylester) conjugate 3 induced time-dependent apoptosis A CaSki, at GI50 concentration, as measured Annexin V-FITC/PI staining. most active coumarin–triazolyl 2g possessed activities, indicated its ability to induce S/G2 phase cycle arrest concentration early CaSki obtained results revealed potential agents, particularly against cancer.

Language: Английский

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