New coumarin derivative with potential antioxidant activity: Synthesis, DNA binding and in silico studies (Docking, MD, ADMET)

Arabian Journal of Chemistry, Journal Year: 2022, Volume and Issue: 16(2), P. 104440 - 104440

Published: Nov. 26, 2022

A new coumarin derivative, 7-((8-(4-benzylpiperidin-1-yl)octyl)oxy)-4-methyl-2H-chromen-2-one (C3), was synthesized by two-step alkylation reaction of 7-hydroxy-4-methyl coumarin. The structure and purity the compound were characterized its 1H 13C NMR, FT-IR LC-MS spectral data. DNA binding interaction C3 evaluated using UV–vis spectrophotometric viscosimetric methods. These experiments showed that bound in intercalative mode. antioxidant activity DPPH method, results displayed had radical scavenging effect. possible mechanism anticancer investigated via molecular docking two enzymes CYP450 EGFR as receptors. also tended a good ability based on result analysis, with affinity values (-7.82 kcal/mol) site interactions. Molecular Dynamics (MD) simulation implemented to elucidate interactions protein–ligand complex 20 ns. ADMET analyzes which paved way for us predict drug candidate performed. All experimental theoretical potential an agent.

Language: Английский

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An Efficient and Versatile Deep Eutectic Solvent-Mediated Green Method for the Synthesis of Functionalized Coumarins

ACS Omega, Journal Year: 2022, Volume and Issue: 7(12), P. 10649 - 10659

Published: March 15, 2022

Herein, we report a green and efficient synthetic route for the construction of diverse functionalized coumarins in good-to-excellent yields (60–98%) via Pechmann condensation. The optimized involves biodegradable, reusable, inexpensive deep eutectic solvent (DES) choline chloride l-(+)-tartaric acid ratio 1:2 at 110 °C. Interestingly, phloroglucinol ethyl acetoacetate, upon reaction, furnished coumarin (20) 98% yield within 10 min. On other front, same DES relatively lower reaction temperature (90 °C) was found to provide bis-coumarins decent (81–97%) 20–45 Moreover, this particular method be quite effective large-scale synthesis without noteworthy reduction desired products. Noticeably, versatile approach, plays dual role as well catalyst, it effectively recycled reused four times with no significant drop-down product.

Language: Английский

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Polymer-Based Long-Lived Phosphorescence Materials over a Broad Temperature Based on Coumarin Derivatives as Information Anti-Counterfeiting

ACS Applied Materials & Interfaces, Journal Year: 2023, Volume and Issue: 15(25), P. 30717 - 30726

Published: June 19, 2023

The development of new polymer-based room-temperature phosphorescence materials is great significance. By a special molecule design and set feasible property-enhancing strategies, coumarin derivatives (CMDs, Ma-Mf) were doped into polyvinyl alcohol (PVA), polyacrylamide (PAM), corn starch, polyacrylonitrile (PAN) as information anti-counterfeiting. CMDs-doped PVA starch films showed long-lived emissions up to 1246 ms (Ma-PVA) 697 (Ma-corn starch), reaching over 10 s afterglow under naked eye observation ambient conditions. Significantly, PAM can display in wide temperature range (100-430 K). For example, the Me-PAM film has lifetime 16 at 430 K. use with strong polarity rigidity expanded long-life phosphorescent materials. present systems provide possibility for developing organic robust phosphorescence.

Language: Английский

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Antidepressant effects of coumarins and their derivatives: A critical analysis of research advances

European Journal of Pharmacology, Journal Year: 2023, Volume and Issue: 956, P. 175958 - 175958

Published: Aug. 4, 2023

Coumarins and their derivatives are non-flavonoids polyphenols with diverse pharmacological activities including anti-depressant effects. This study systematically examines the antidepressant effects of coumarins in relation to time series research progress pathways, association other diseases, toxicity bliometric analysis. The review was approached using Preferred Reporting Items for Systematic Reviews Meta-Analyses (PRISMA) coupled R package Biblioshiny, a web interface Bibliometrix analysis VOSviewer software analytic tools. Literature searches were conducted Scopus, Web Science, PubMed from inception through January 21, 2023. Coumarins, depression, coumarin treatment main search terms used which resulted inclusion 46 eligible publications. Scopoletin, psoralen, 7-hydroxycoumarin, meranzin hydrate, osthole, esculetin/umbelliferone most studied exerted stronger affinity monoamine oxidase-B (MAO-B) inhibition and, inhibitory effect via neurotransmitter pathway on MAO is well-studied. However, epigenetic modification, neuroendocrine, neurotrophic pathways understudied. Recent focuses targeted cytokines fibromyalgia. There link between gut microbiome, brain, depression; hydrate exerts an activity by remodelling gastrointestinal system. We established that empirical data some support limited. Likewise, safe dosage range several yet be fully determined.

Language: Английский

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Benzopyrone, a privileged scaffold in drug discovery: An overview of FDA‐approved drugs and clinical candidates

Medicinal Research Reviews, Journal Year: 2024, Volume and Issue: 44(5), P. 2035 - 2077

Published: March 26, 2024

Abstract Natural products have always served as an important source of drugs for treating various diseases. Among privileged natural product scaffolds, the benzopyrone class compounds has a substantial presence among biologically active compounds. One pioneering anticoagulant drugs, warfarin approved in 1954 bears benzo‐α‐pyrone (coumarin) nucleus. The widely investigated psoriasis methoxsalen, and trioxsalen, also contain Benzo‐γ‐pyrone (chromone) containing cromoglic acid, pranlukast were treatments asthma 1982 2007, respectively. Numerous other small molecules with core are under clinical investigation. present review discusses discovery, absorption, distribution, metabolism, excretion properties, synthetic approaches Food Drug Administration‐approved clinical‐stage role pyrone biological activity been discussed. unravels potential medicinal chemistry drug development.

Language: Английский

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

Results in Chemistry, Journal Year: 2024, Volume and Issue: 8, P. 101611 - 101611

Published: June 1, 2024

Despite the up-to-date advancements in its treatment, cancer is still being harvested lives of millions people annually; this health threat necessitates exploring more potent agents that can effectively fight it. The class heterocycles known as coumarin, and natural synthetic derivatives are thought to be biomedically valuable. Coumarins have low side effects, outstanding selectivity, a straightforward design for maximum efficiency, various pharmacological actions. For these characteristics, coumarins continuously isolated from sources synthesized laboratories, alongside with examining them possible bioactivities. In addition garnering significant attention, coumarin has emerged valuable scaffold potentially important precursor development innovative anticancer medicines. Researchers working create new cancer-fighting coumarins, well investigating old ones. Integration two or cyclic moieties into single molecular framework might enhance existing effects perhaps provide entirely Numerous studies shown synergistic additive impact when fused where fusion may occur at coumarin-benzene coumarin-lactone. current paper explores detail how linearly ring-fused combat cancer. derivative number 42 was determined best among were reviewed. Compared 5-flourouracil, IC50 values against six cell lines promising. These 25.08, 13.42, 41.45, 28.43, 31.15, 13.08 μM SK-OV-3, HeLa, KYSE-30, AMN3, SKG, MCF-7, respectively. attribute obvious compared those reference, which following same order lines: 22.43, 13.37, 30.72, 24.89, 22.12, 12.42 μM. researchers conducted searches across multiple data repositories, such Scopus, Google Scholar, Web Science, PubMed. After conducting thorough analysis, authors found included 59 pertinent publications published by end 2023. reviewed help medicinal chemists manufacture functionally active leads using scaffolds been mentioned. knowledge derived offer substantial medical benefits short term powerful drugs could boost chemotherapeutics.

Language: Английский

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Physical and optoelectronic characteristics of novel low-cost synthesized coumarin dye-based metal-free thin films for light sensing applications

Materials Science in Semiconductor Processing, Journal Year: 2021, Volume and Issue: 137, P. 106225 - 106225

Published: Sept. 29, 2021

Language: Английский

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Medicinal significance of novel coumarin analogs: Recent studies

Results in Chemistry, Journal Year: 2022, Volume and Issue: 4, P. 100313 - 100313

Published: Jan. 1, 2022

Coumarin is a versatile scaffold with outstanding biological potential and played key role in the field of medicine. The benzopyran-2-one ring bearing heterocycles are known for antimicrobial, anti-cancer, antioxidant activities. This review article provides recent clinical significance reports coumarin coumarin-fused heterocycles. Further, this focus on feature derivatives like antimalarial, anti-HIV, anti-tubercular, above activities make molecule more fascinating invention new novel analogs.

Language: Английский

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Recent Advances in Biologically Active Coumarins from Marine Sources: Synthesis and Evaluation

Marine Drugs, Journal Year: 2022, Volume and Issue: 21(1), P. 37 - 37

Published: Dec. 31, 2022

Coumarin and its derivatives have significantly attracted the attention of medicinal chemists chemical biologists due to their huge range biological, in particular, pharmacological properties. Interesting families coumarins been found from marine sources, which has accelerated drug discovery process by inspiring innovation or even identification analogues with remarkable biological The purpose this review is showcase most interesting marine-derived a chemistry point view, as well novel useful synthetic routes described date achieve these structures. references that compose overview were collected PubMed, Mendeley SciFinder.

Language: Английский

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Coumarin-Resveratrol-Inspired Hybrids as Monoamine Oxidase B Inhibitors: 3-Phenylcoumarin versus trans-6-Styrylcoumarin

Molecules, Journal Year: 2022, Volume and Issue: 27(3), P. 928 - 928

Published: Jan. 29, 2022

Monoamine oxidases (MAOs) are attractive targets in drug design. The inhibition of one the isoforms (A or B) is responsible for modulating levels different neurotransmitters central nervous system, as well production reactive oxygen species. Molecules that act selectively on MAO have been studied deeply, and coumarin has described a promising scaffold. In current manuscript we describe comparative study between 3-phenylcoumarin (endo coumarin-resveratrol-inspired hybrid) trans-6-styrylcoumarin (exo hybrid). Crystallographic structures both compounds were obtained analyzed. 3D-QSAR models, particular CoMFA CoMSIA, docking simulations molecular dynamics performed to support better understand interaction these molecules with isoforms. Both proved inhibit MAO-B, being 107 times more active than 3-phenylcoumarin, 267 trans-resveratrol.

Language: Английский

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