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

RSC Advances, Journal Year: 2025, Volume and Issue: 15(5), P. 3756 - 3828

Published: Jan. 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.

Language: Английский

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

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(8)

Published: Jan. 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.

Language: Английский

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

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(1)

Published: Jan. 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.

Language: 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, Journal Year: 2025, Volume and Issue: unknown

Published: March 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

Language: Английский

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

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1308, P. 138142 - 138142

Published: March 24, 2024

Language: 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

Published: April 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.

Language: 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, Journal Year: 2023, Volume and Issue: 12(8)

Published: July 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.

Language: Английский

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

Topics in Current Chemistry, Journal Year: 2024, Volume and Issue: 382(2)

Published: April 12, 2024

Language: Английский

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Regioselective Annulation of 3(5)‐Aminopyrazole with Aryl Ketones or Aryl Alkynes Using <i>N</i>,<i>N</i>‐Dimethylethanolamine as a Single/Triple Carbon Synthon

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3591 - 3596

Published: June 19, 2024

Abstract An efficient and regioselective cyclization for construction of pyrazolo[3,4‐ b ]pyridines methylene‐bridged bis(pyrazolo[1,5‐ a ]pyrimidines) has been established. It involves [3+2+1] annulation 3(5)‐aminopyrazole, N,N ‐dimethylethanolamine (DMEA), with 1,2‐insertion aryl methyl ketones or 2,1‐insertion alkynes. DMEA is oxidized through C( sp 3 )‐H activation to provide single triple carbon source.

Language: Английский

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Synthesis of Fused Pyrimidines from Azole Amines and Their Biological Activity

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(43)

Published: Aug. 3, 2024

Abstract Fused pyrimidines are a class of heterocyclic compounds that have gained considerable interest due to their extensive biological activities and potential applications in drug development. This review article aims provide comprehensive overview the latest synthetic approaches fused pyrimidines, including Michael reactions, multicomponent metal‐catalyzed photocatalytic peroxide‐mediated inverse electron demand Diels–Alder reactions. Furthermore, these compounds, such as ability combat cancer microbial infections, also discussed. summarizes existing literature on synthesis activity from 2020 2023. We hope this will inspire development more effective less toxic pyrimidine drugs with well‐designed structures.

Language: Английский

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