Syntheses, reactivity, and biological applications of coumarins

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 12

Published: Feb. 19, 2024

This comprehensive review, covering 2021-2023, explores the multifaceted chemical and pharmacological potential of coumarins, emphasizing their significance as versatile natural derivatives in medicinal chemistry. The synthesis functionalization coumarins have advanced with innovative strategies. enabled incorporation diverse functional fragments or construction supplementary cyclic architectures, thereby biological physico-chemical properties compounds obtained were enhanced. unique structure coumarine facilitates binding to various targets through hydrophobic interactions pi-stacking, hydrogen bonding, dipole-dipole interactions. Therefore, this important scaffold exhibits promising applications uncountable fields chemistry (e.g., neurodegenerative diseases, cancer, inflammation).

Language: Английский

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Toxicity and Biodistribution of Fragmented Polypropylene Microplastics in ICR Mice

International Journal of Molecular Sciences, Journal Year: 2023, Volume and Issue: 24(10), P. 8463 - 8463

Published: May 9, 2023

Currently, polypropylene (PP) is used in various products, thus leading to high daily exposure humans. Thus, it necessary evaluate the toxicological effects, biodistribution, and accumulation of PP microplastics human body. In this study, administration two particle sizes (approximately 5 10-50 µm) did not lead any significant changes several evaluation parameters, including body weight pathological examination, compared with control group ICR mice. Therefore, approximate lethal dose no-observed-adverse-effect level mice were established as ≥2000 mg/kg. Furthermore, we manufactured cyanine 5.5 carboxylic acid (Cy5.5-COOH)-labeled fragmented monitor real-time vivo biodistribution. After oral Cy5.5-COOH-labeled mice, most detected gastrointestinal tract observed be out after 24 h IVIS Spectrum CT. study provides a new insight into short-term toxicity, distribution, mammals.

Language: Английский

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Coumarins: Quorum Sensing and Biofilm Formation Inhibition

Molecules, Journal Year: 2024, Volume and Issue: 29(19), P. 4534 - 4534

Published: Sept. 24, 2024

Quorum sensing (QS) is a bacterial cell-to-cell communication mechanism that plays an essential role in pathogenesis. QS governs behavior and controls biofilm formation, which turn contributes to antibiotic resistance. Therefore, identifying synthesizing novel compounds overcome inhibit formation are essential. Coumarins important plant-derived natural products with wide-ranging bioactivities extensive applications, including antibacterial, antifungal, anticoagulant, antioxidant, anticancer, anti-inflammatory properties. Additionally, coumarins capable of rewiring inhibition, leading higher susceptibility antimicrobial agents less this review, we aim provide overview formation. This review also discusses the synthesized controlling QS, inhibiting inducing synergy antibiotic–coumarin combinations. Hence, emphasizes potential coumarin act as antibacterial demonstrates their ability alleviate

Language: Английский

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Copper-Catalyzed Asymmetric Propargylic [3 + 2] Cycloaddition: Synthesis of Enantioenriched Dihydrofuro[3,2-c]coumarins and its Quinolinone and Thiocoumarin Analogues

Organic Letters, Journal Year: 2023, Volume and Issue: 25(20), P. 3733 - 3738

Published: May 16, 2023

A copper(II)-P,N,N-ligand catalyzed propargylic [3 + 2] cycloaddition approach for the synthesis of optically enriched dihydrofuro[3,2-c]coumarins has been accomplished first time. The utilizes esters as C2-bis-electrophiles and 4-hydroxycoumarin derivatives C,O-bis-nucleophiles. In addition, this novel strategy was also explored with 4-hydroxy-2-quinolinones 4-hydroxythiocoumarins. Moreover, various their quinolinone thiocoumarin analogues were synthesized in moderate to good yields high enantioselectivities.

Language: Английский

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Organ-specific accumulation and toxicity analysis of orally administered polyethylene terephthalate microplastics

Scientific Reports, Journal Year: 2025, Volume and Issue: 15(1)

Published: Feb. 24, 2025

Microplastics (MPs), plastic particles with a diameter of < 5 mm, are intentionally produced or formed by the breakdown variety larger plastics. Polyethylene terephthalate (PET) is common source MPs and PET-MPs prevalent in environment. Owing to their persistence, can enter ecosystems, air, food sources, posing significant health risks. This study aimed investigate toxicological effects vivo accumulation smaller than 10 µm. To track biodistribution, fluorescently labeled were prepared. Particle size morphology confirmed using physical chemical characterization. Following oral administration ICR (CD-1®) outbred mice, occurred predominantly lungs, as IVIS spectrum CT analysis ex imaging. Toxicity assays revealed development granulomatous inflammation lungs at medium high doses, indicating concentration-dependent response. The recorded no-observed-adverse-effect levels 1.75 mg/kg for males 7 females. highlights potential induce persistent respiratory tissues reveals need further research support regulatory standards long-term MP exposure.

Language: Английский

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Multicomponent Synthesis of Structurally Diverse Spiroheterocycles using Bio-organic Catalyst in Aqueous Medium

Current Organocatalysis, Journal Year: 2024, Volume and Issue: 11(4), P. 321 - 329

Published: Feb. 2, 2024

Background: MCRs are one of the most significant tools in synthesis organic compounds. MCR is a rapid chemical technique that uses three or more reactants to produce products sustain all structural and substructural properties initial components. useful fields synthetic chemistry because their rate reaction, simple procedure excellent yields. We reported an efficient environmentally friendly domino approach for spiroheterocycles spiro annulated with indeno[1,2-b]quinoline. Method: The privileged heterocyclic substructures have been synthesized using taurine (2-aminoethanesulfonic acid) as green, sustainable, bio-organic recyclable catalyst three-component reaction isatins, 1,3-diketones, 1-napthylamine aqueous media. present method probably first report synthesize spiroheterocycles, spiroannulated Furthermore, valuable yield results from 15-20 min. Result: optimization conditions important case synthesis. solvent, temperature, time loading were examined. reusability was also investigated experimentally. used has high activity well good reusability. protocol will be extended synthesise library hybrid cost-effective, time-efficient easy-workup methodology gives outstanding yields (80–95%) 15–20 Conclusion: Taurine-catalyzed multicomponent novel indeno[1,2-b]quinolines. catalytic water green solvent makes process friendly. special features include efficiency, operational simplicity, it expected make contributions not only drug discovery studies but pharmaceutical therapeutic view introducing molecular diversity molecules.

Language: Английский

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Synthetic Routes to Access Dicarbonylated Aryls and Heteroaryls

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The regioselective 1,2-dicarbonylation of aryls and heteroaryls offers access to functionalized dicarbonylated heteroaryls, which opens pharmaceuticals bioactive molecules with diverse synthetic utility.

Language: Английский

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4″-Alkyl EGCG Derivatives Induce Cytoprotective Autophagy Response by Inhibiting EGFR in Glioblastoma Cells

ACS Omega, Journal Year: 2024, Volume and Issue: 9(2), P. 2286 - 2301

Published: Jan. 3, 2024

Epidermal growth factor receptor (EGFR)-targeted therapy has been proven vital in the last two decades for treatment of multiple cancer types, including nonsmall cell lung cancer, glioblastoma, breast and head neck squamous carcinoma. Unfortunately, majority approved EGFR inhibitors fall into drug resistance category because continuous mutations acquired resistance. Recently, autophagy surfaced as one emerging underlying mechanisms behind to EGFR-tyrosine kinase (TKIs). Previously, we developed a series 4″-alkyl EGCG (4″-Cn EGCG, n = 6, 8, 10, 12, 14, 16, 18) derivatives with enhanced anticancer effects stability. Therefore, current study hypothesized that might induce cytoprotective upon inhibition, inhibition may lead improved cytotoxicity. In this study, have observed caspase-3-dependent apoptosis derivative-treated glioblastoma cells (U87-MG). We also confirmed could inhibit cells, well mutant L858R/T790M EGFR, through an vitro assay. Furthermore, found induces autophagic responses, accompanied by blockage AKT/mTOR signaling pathway. addition, cytotoxicity caused 4″-C10 4″-C12 4″-C14 was significantly increased after pharmacological inhibitor chloroquine. These findings enhance our understanding response toward suggest potent combinatorial strategy increase therapeutic effectiveness EGFR-TKIs.

Language: Английский

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Recent Advances on Sustainable Synthesis of Furocoumarins

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(7)

Published: Feb. 12, 2024

Abstract Being an important constituent of naturally occurring heterocyclic compounds with a myriad interesting biological activities, the furocoumarin motif has claimed vast interest in synthetic and medicinal research. Designing organic synthesis following green sustainable approach finds special importance terms energy efficiency, cost‐effectiveness hence becoming domain research recent past. The methodologies for presented here particularly include strategies developed under microwave irradiation, solvent‐free conditions or uses solvent, metal‐free routes, room temperature mediated one‐pot MCR reactions. This review article attempts to highlight advances furocoumarins along general aspects like natural occurrence, activities this particular scaffold.

Language: Английский

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Entry to 4,5-Fused Coumarin frameworks via Radical-Promoted Alkylative Intramolecular C5-Annulation

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6385 - 6392

Published: Jan. 1, 2024

A silver-catalyzed oxidative protocol for the synthesis of previously unfamiliar 4,5-fused coumarins is disclosed.

Language: Английский

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