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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An ultrasound assisted, ionic liquid-molecular iodine synergy driven efficient green synthesis of pyrrolobenzodiazepine-triazole hybrids as potential anticancer agents

Frontiers in Pharmacology, Journal Year: 2023, Volume and Issue: 14

Published: May 5, 2023

Herein, we report an efficient and eco-friendly, ultrasound assisted synthetic strategy for the construction of diversified pyrrolobenzodiazepine-triazole hybrids, which are potentially pharmaceutically important scaffolds, via a domino reaction involving intermolecular electrophilic substitution followed by intramolecular Huisgen 1,3-dipolar azide-alkyne cycloaddition. The USP reported protocol is use benign inexpensive, recyclable molecular iodine-ionic liquid synergistic catalytic system cum media achieving synthesis. other salient features this method mild conditions, high yield atom economy, operational simplicity, broad substrate scope easy workup purification. All synthesized compounds were evaluated in vitro anti-proliferative activity against various cancer cell lines. From among title compounds, 9,9-dimethyl-8-phenyl-9H-benzo [b]pyrrolo [1,2-d][1,2,3]triazolo[5,1-g][1,4]diazepine (7) was found most to be active compound exhibiting IC50 value 6.60, 5.45, 7.85, 11.21, 12.24, 10.12, 11.32 µM MCF-7, MDA-MB-231, HeLa, SKOV-3, A549, HCT-116 DLD-1 lines, respectively. Further non-toxic normal human embryonic kidney (HEK-293) line.

Language: Английский

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Recent developments in calix[4]pyrrole (C4P)-based supramolecular functional systems

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(22), P. 6416 - 6440

Published: Jan. 1, 2022

Recent advances with calix[4]pyrrole-based supramolecular functional entities in the fields of molecular recognition (receptors, sensors, and metal ion caged systems), self-assembly (polymers), photo/pH-responsive switches catalysis are reviewed.

Language: Английский

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N-, O- and S-Heterocycles Synthesis in Deep Eutectic Solvents

Molecules, Journal Year: 2023, Volume and Issue: 28(8), P. 3459 - 3459

Published: April 14, 2023

The synthesis of heterocycles is a fundamental area organic chemistry that offers enormous potential for the discovery new products with important applications in our daily life such as pharmaceuticals, agrochemicals, flavors, dyes, and, more generally, engineered materials innovative properties. As heterocyclic compounds find application across multiple industries and are prepared very large quantities, development sustainable approaches their has become crucial objective contemporary green committed to reducing environmental impact chemical processes. In this context, present review focuses on recent methodologies aimed at preparing N-, O- S-heterocyclic Deep Eutectic Solvents, class ionic solvents non-volatile, non-toxic, easy prepare, recycle, can be obtained from renewable sources. Emphasis been placed those processes prioritize recycling catalyst solvent, they offer dual benefit promoting synthetic efficiency while demonstrating responsibility.

Language: Английский

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Dithieno[3,2-b:2′,3′-d]thiophene (DTT): an emerging heterocyclic building block for future organic electronic materials & functional supramolecular chemistry

RSC Advances, Journal Year: 2022, Volume and Issue: 12(55), P. 36073 - 36102

Published: Jan. 1, 2022

DTT: a potential electron rich building block and its diverse application in organic electronic materials.

Language: Английский

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Metal-free C(sp³)–H functionalization (C–C and C–N bond formation) of 1,2,3,4-tetrahydroacridines using deep eutectic solvents as catalyst and reaction medium

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(7), P. 1434 - 1440

Published: Jan. 1, 2024

A simple and efficient protocol for the addition of azodicarboxylates (C–N bond) maleimides (C–C at C4-position 1,2,3,4-tetrahydroacridines was achieved under metal-free conditions using deep eutectic solvents with high atom efficiency, regioselectivity, yields.

Language: Английский

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A facile catalyst-free one-pot three component synthesis of pharmacologically important indole-centered 4H-chromenes in a deep eutectic solvent (DES)

Journal of Molecular Liquids, Journal Year: 2023, Volume and Issue: 390, P. 122951 - 122951

Published: Aug. 30, 2023

Language: Английский

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One‐Walled Phthalimide Extended Calix[4]Pyrrole‐Based Supramolecular Adsorbent for Alleviating Nitrate From Simulated Water

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(5)

Published: Jan. 30, 2025

Abstract In this investigation, meso ‐substituted one‐walled phthalimide appended calix[4]pyrrole ( m Pth–C4P) was prepared from pthalimide functionalized dipyrromethane (DPM, 4 ), acetone, and freshly distilled pyrrole via both conventional as well green protocols utilizing the deep eutectic solvent (DES) of N,N' ‐dimethyl urea (DMU) & l ‐(+)‐tartaric acid (TA) in an appropriate ratio 7:3. order to lessen nitrate (NO 3 − ) ion endowed eutrophication peril, Pth–C4P effectively employed a supramolecular adsorbent for sequestration NO aquatic phase. The extensively characterized by FTIR, 1 H‐NMR, SEM–EDX, elemental mapping corroborate synthesis adsorption ion. surface area found be 11.465 2 g −1 pore size 3.2 nm, pointed out mesoporous nature Pth–C4P. Batch methodology exploited detailing influence process parameters on %efficiency capacity. demonstrated excellent competence (> 91%) within 16 min [NO ] 20 mg L , which translates into good pseudo‐second rate constant value 0.026 . Freundlich model best‐fit pointing multilayer adsorption. maximum saturation capacity 239.03 ‒1 at 298 K, is far better than most reported adsorbents indicating potential confiscate dynamics appraisal elucidated favor uptake with intraparticle liquid film diffusion models governing reaction. Thermodynamic suggested that spontaneous, favorable, exothermic harmony isotherm studies. can used consecutively up cycles along real water > 80% uptake. All these results established efficacious scavenger simulated water.

Language: Английский

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Aromaticity monitoring during the donor-acceptor coordination of pyrosilicate, pyrophosphate, and pyrosulfate anions to a new designed anion receptor

Phosphorus, sulfur, and silicon and the related elements, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 10

Published: April 16, 2025

Language: Английский

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The Piloty-Robinson Reaction: A Versatile Tool for the Synthesis of 3,4-Disubstituted Pyrroles

Polycyclic aromatic compounds, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 21

Published: June 3, 2025

Language: Английский

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