Advances in pyrazolo[1,5-a]pyrimidines: synthesis and their role as protein kinase inhibitors in cancer treatment

RSC Advances, Год журнала: 2025, Номер 15(5), С. 3756 - 3828

Опубликована: Янв. 1, 2025

Pyrazolo[1,5- a ]pyrimidines are notable class of heterocyclic compounds with potent protein kinase inhibitor (PKI) activity, playing critical role in targeted cancer therapy.

Язык: Английский

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Rose‐Bengal‐Photocatalyzed Cross‐Dehydrogenative Coupling Reactions under Visible Light

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(8)

Опубликована: Янв. 19, 2024

Abstract Over the past few years, organic chemistry has used dye rose bengal‘s ability to absorb visible light. In present‐day research, innovation of environmentally friendly processes for carbon‐carbon/carbon‐heteroatoms (Nitrogen, Oxygen, Sulphur, and Phosphorus) bond formation great importance. The photocatalyzed cross‐dehydrogenative coupling (CDC) reactions using bengal (RB) is a promising technique creating carbon‐carbon/carbon‐heteroatom bonds directly from readily available compounds. Our review focuses on current advancement in that uses bond‐making synthesize various important molecules via CDC reactions.

Язык: Английский

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Oxone® Mediated Regioselective C(sp²)−H Selenylation and Thiocyanation of Pyrazolo[1,5‐a]pyrimidines at Room Temperature

ChemistrySelect, Год журнала: 2024, Номер 9(1)

Опубликована: Янв. 2, 2024

Abstract A mild Oxone® mediated reaction for direct regioselective C−H selenylation and thiocyanation of pyrazolo[1,5‐ a ]pyrimidines is established at ambient temperature. This practical efficient methodology employs as user friendly, green, non‐toxic cheap reagent to facilitate room The present method offers high regioselectivity, broad substrate scope, conditions excellent yields. Further, this eco‐friendly approach could easily be extended other heterocycles. Mechanistic studies indicate that the occurs through electrophilic substitution mechanism via generation an chalcogen species.

Язык: Английский

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PIFA-mediated room temperature dehydrogenative annulation for the synthesis of 2-alkenyl oxazoles

Journal of Molecular Structure, Год журнала: 2024, Номер 1308, С. 138142 - 138142

Опубликована: Март 24, 2024

Язык: Английский

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I₂-Catalyzed Cascade Annulation/Cross-Dehydrogenative Coupling: Excellent Platform to Access 3-Sulfenyl Pyrazolo[1,5-a]pyrimidines with Potent Antibacterial Activity against Pseudomonas aeruginosa and Staphylococcus aureus

ACS Applied Bio Materials, Год журнала: 2025, Номер unknown

Опубликована: Март 19, 2025

The increasing resistance of bacteria to antibiotics has become a serious threat existing options for treating bacterial infections. We have developed synthetic methodology 3-sulfenyl pyrazolo[1,5-a]pyrimidines with potent antibacterial activity. This iodine-catalyzed strategy been by employing amino pyrazoles, enaminones/chalcones, and thiophenols through intermolecular cyclization subsequent cross-dehydrogenative sulfenylation. highly regioselective practicable protocol utilized synthesize structurally diverse wide functionalities. is also extendable toward the synthesis bis(pyrazolo[1,5-a]pyrimidin-3-yl)sulfanes from pyrazole, enaminones/chalcone, KSCN pyrazolo[1,5-a]pyrimidine direct acetophenone. Mechanistic investigation disclosed radical pathway C-H sulfenylation involvement 3-iodo as active intermediate. biological activity sulfenyl against Pseudomonas aeruginosa Staphylococcus aureus, whereas sulfinyl no such Sulfenyl mechanistically inhibited growth accumulation ROS well induction in lipid peroxidation. Subsequently, circumstances changed membrane potential facilitated interaction membrane-associated proteins, leading loss integrity damage cell membranes. Moreover, these derivatives potentiated efficacy commercial antibiotic ciprofloxacin selected strains can be considered an alternative therapy

Язык: Английский

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Electrochemical Regioselective C(sp2)-H Bond Chalcogenation of Pyrazolo[1,5-a]pyrimidines via Radical Cross Coupling at Room Temperature

Опубликована: Апрель 9, 2024

In this report, we disclose an electrochemical approach for the C(sp2)-H chalcogenation of pyrazolo[1,5-a]pyrimidines at room temperature via radical cross-coupling reaction. The reaction takes place within undivided cell employing graphite electrodes, with TBABF4 acting as supporting electrolyte. This technique offers a rapid, oxidant-free, and environmentally conscious protocol achieving regioselective specifically C3 position pyrazolo[1,5-a]pyrimidines. Furthermore, procedure uses only 0.5 equivalents diaryl chalcogenides which underscores atom economy protocol. Key attributes methodology include mild conditions, short time, utilization cost-effective electrode materials, reliable achievement yields ranging from good to excellent friendly conditions. Cyclic voltammetry studies quenching experiments suggest pathway mechanism.

Язык: Английский

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Visible-Light-Mediated, Organophotocatalytic C–H Thiocyanation of Pyrazolo[1,5-a]pyrimidines

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13215 - 13223

Опубликована: Сен. 11, 2024

Herein, we report a metal-free, organophotoredox-catalyzed sustainable C-H thiocyanation of biologically active class N-heterocycles, pyrazolo[1,5-

Язык: Английский

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Metal‐, Oxidant‐, and Additive‐Free Sulfenylation of Imidazo[1,2‐a]pyridines Using Sulfenamides and an I₂ Catalyst

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(8)

Опубликована: Июль 14, 2023

Abstract A novel sulfenylation reagent (sulfenamide) was applied to establish a simple and efficient process convert C−H bond in imidazo[1,2‐ ]pyridine C−S bond. This only requires sulfenamides as the I 2 an inexpensive readily available catalyst, without using metal catalysts, oxidants, additives, or even light radiation. The proposed reaction features excellent reactivity, substrate compatibility, regioselectivity.

Язык: Английский

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Tunable Regioselective Allylic Alkylation/Iodination of Imidazoheterocycles in Water

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(3), С. 1492 - 1504

Опубликована: Янв. 12, 2024

The switchable roles of allylic alcohol and molecular iodine as reagents catalysts have been demonstrated in the regioselective alkylation iodination imidazoheterocycles employing mixture alcohol-I2. First, we explored catalytic activity for allylation using an aqueous medium. a library other electron-rich heterocycles like indole, pyrazole, 4-hydroxy coumarin, 6-amino uracil has achieved by this methodology. efficiency I2 catalyst N-allylation azoles also demonstrated. Next, shown that could be beneficial under room temperature. Mechanistic studies indicate activation took place probably through halogen bonding, NMR show reaction did not proceed ether formation.

Язык: Английский

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Pushing Boundaries: What’s Next in Metal-Free C–H Functionalization for Sulfenylation?

Topics in Current Chemistry, Год журнала: 2024, Номер 382(2)

Опубликована: Апрель 12, 2024

Язык: Английский

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