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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Chiral Cp^xRhodium(III)‐Catalyzed Enantioselective Aziridination of Unactivated Terminal Alkenes

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(12)

Published: Jan. 27, 2024

Chiral cyclopentadienyl-rhodium(III) Cp

Language: Английский

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Preparation of a Novel Trimethoprim/Oxidized Pectin/Ti-MOF Nanoplymer as a Super Bioactive Agent

Journal of Inorganic and Organometallic Polymers and Materials, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 4, 2025

Language: Английский

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Organic Dye-Sensitized Nitrene Generation: Intermolecular Aziridination of Unactivated Alkenes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3251 - 3258

Published: Feb. 15, 2024

Aziridines are important structural motifs and intermediates, several synthetic strategies for the direct aziridination of alkenes have been introduced. However, many these require an excess activated alkene, suffer from competing side-reactions, limited functional group tolerance, or involve precious transition metal-based catalysts. Herein, we demonstrate by combining sulfonyl azides as a triplet nitrene source with catalytic amount organic dye functioning photosensitizer. We show how nature azide, in combination triplet-excited state energy photosensitizer, affects yield provide mechanistic rationale to account observed dependence reaction on azide reagents. The optimized conditions enable structurally diverse complex alkenes, carrying various groups, alkene limiting reagent.

Language: Английский

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A “phosphorus derivative” of aziridines: on the importance of ring strain energy and three heteropolar bonds in azaphosphiridines

Dalton Transactions, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Compared to aziridines, azaphosphiridines, which formally result from the replacement of a carbon atom by phosphorus, have been much less studied. In this work, accurate values for one most prominent properties, ring strain energy (RSE), theoretically examined wide range azaphosphiridine derivatives. Strongly related aspects interest developing use azaphosphiridines in heteroatom and polymer chemistry are opening reactions polymerisations, latter facilitated their significantly high RSE. While methyl groups little influence on RSE, complexation with different metal moieties increases RSE all cases, an increase was also found upon oxidation corresponding P-oxides other σ5λ5-P The highest P-protonated azaphosphiridinium cation exocyclic double bonds. A correlation RSEs relaxed force constants endocyclic bonds AIM-derived parameters critical points, such as electron density, ρ(r), Lagrangian kinetic energy, G(r), found. relatively low barrier P-C bond cleavage via nucleophilic attack MeNH2 phosphorus points possibility ring-opening polymerisation.

Language: Английский

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Reversible deprotonation as crucial step in bispidine copper-catalyzed aziridination reaction

Inorganica Chimica Acta, Journal Year: 2025, Volume and Issue: unknown, P. 122587 - 122587

Published: Feb. 1, 2025

Language: Английский

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Phytotherapeutic Analysis of Chloroform-Based Fractions of Alstonia scholaris and Wrightia tinctoria Extracts Reveals Potent Anti-Psoriatic Activity: An In Vitro and In Vivo Study

Pharmaceuticals, Journal Year: 2025, Volume and Issue: 18(3), P. 304 - 304

Published: Feb. 22, 2025

Background/Objectives: Psoriasis, a prevalent dermatological disorder, poses therapeutic challenges due to limited effective treatments or adverse side-effects. Traditional medicinal plants like Alstonia scholaris and Wrightia tinctoria, historically used in Ayurvedic Siddha practices, show potential treating inflammatory skin diseases. This study aims explore their vitro vivo anti-psoriatic properties develop safer more therapies. Methods: Chloroform:methanol fractions from ethanol extracts of tinctoria were evaluated for activity. In assays using HaCaT cells assessed cell viability, apoptosis, markers. studies utilized an IMQ-induced psoriasis mouse model, evaluating lesions, histopathology, cytokine profiles. Results: Chloroform significantly reduced viability induced apoptosis. They also dose-dependently downregulated IL-8 RANTES levels. vivo, these inflammation, edema, scores. Histopathological analysis showed decreased epidermal thickness dermal inflammation. Key biomarkers IL-17 IL-23 reduced. Conclusions: demonstrated potent effects vivo. These findings support as novel phytotherapeutic agents managing psoriasis, offering promise further development clinical application.

Language: Английский

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Recent advances in the application of contiguously functionalized aziridines for the synthesis of pharmaceutical precursors via regioselective ring-opening reactions

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 576, P. 114943 - 114943

Published: Feb. 26, 2025

Language: Английский

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Regioselective, Lewis Acid-Catalyzed Ring-Openings of 2,3-Aziridyl Alcohols with Azoles

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

Published: April 25, 2025

Methods for regioselective ring-opening reactions of N-sulfonyl-protected aziridyl alcohols with azole nucleophiles have been developed. Several classes azoles, including indazole, substituted pyrazole, benzotriazole, and tetrazole, employed as reaction partners, giving rise to C3-selective opening >3:1 N-selectivity. BF3•OEt2 is the optimal catalyst most substrate combinations, although examples where diphenylborinic acid (Ph2BOH) provides higher yields, or proceed efficiently without a catalyst, are also described. Computational modeling BF3•OEt2-catalyzed consistent observed regiochemical outcome. The calculated transition state appears be stabilized by an unconventional OH···FB hydrogen-bonding interaction.

Language: Английский

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Photocatalytic Nitrene Radical Anion Generation from Sulfonyl Azides for Intermolecular Aziridination of Unactivated Alkenes

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

Published: May 3, 2025

Aziridines are important structures in the contemporary organic synthesis and used for several biological applications. Herein, we show that aziridines can be readily synthesized from alkenes by reductive activation of sulfonyl azides, mediated photoredox catalysis. Mechanistic studies indicate reaction proceeds through reactive nitrene radical anions instead more commonly encountered triplet nitrenes. A substrate scope is performed showed good functional group compatibility.

Language: Английский

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