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Review
Biochemistry & Molecular Biology
Wei-Syuan Lin et al.
Summary: This review provides an overview of the versatile ligands called protic pyrazoles in various fields. It first surveys the coordination chemistry of pincer-type 2,6-bis(1H-pyrazol-3-yl)pyridines, which show significant advances in the last decade. Then it describes the stoichiometric reactivities of protic pyrazole complexes with inorganic nitrogenous compounds, possibly relating to the inorganic nitrogen cycle in nature. Finally, the review outlines the catalytic application of protic pyrazole complexes, emphasizing the mechanistic aspect and discussing the role of the NH group in the protic pyrazole ligand and resulting metal-ligand cooperation in these transformations.
Article
Biochemistry & Molecular Biology
Lyudmila Kayukova et al.
Summary: Nitrobenzenesulfochlorination of beta-aminopropioamidoximes results in a variety of products depending on the initial interacting substances and reaction conditions. The presence of six-membered N-heterocycles in the amidoximes leads to the formation of spiropyrazolinium ortho- or para-nitrobenzenesulfonates through an intramolecular heterocyclization reaction. Different compounds exhibit regioselectivity and regiospecificity, producing different products at different temperatures. The antidiabetic screening of these nitrobezenesulfochlorination amidoximes has shown promising results.
Review
Biochemistry & Molecular Biology
Ana Donaire-Arias et al.
Summary: This review presents an analysis of the diversity of substituents in Pyrazolo[3,4-b]pyridines, as well as the synthetic methods used for their synthesis and their biomedical applications.
Article
Biochemistry & Molecular Biology
Arturo Gamonal Ruiz-Crespo et al.
Summary: A three-step synthetic route for the preparation of nonsymmetrical bisazolyl 2,4,6-trisubstituted pyridines with different substituents on the pyrazole, indazole, and pyridine heterocycles is described. These synthetic modules can serve as optimal building blocks for tuning the chelating and photophysical properties in complex compounds and metalloorganic structures.
Review
Biochemistry & Molecular Biology
Andrzej Danel et al.
Summary: This paper summarizes over 100 years of research on the synthesis, photophysical and biological properties of 1H-pyrazolo[3,4-b]quinolines published from 1911 to 2021. The main synthesis methods, including Friedlander condensation, synthesis from anthranilic acid derivatives, multicomponent synthesis, and others, are described. The potential applications of this class of compounds as fluorescent sensors and biologically active compounds are demonstrated. This review aims to provide an overview of the aforementioned aspects in 1H-pyrazolo[3,4-b]quinoline chemistry, with some of the presented results originating from the authors' laboratories.
Review
Biochemistry & Molecular Biology
Vera L. M. Silva et al.
Summary: This review describes the properties, synthetic approaches, and versatile applications of vinylpyrazoles as building blocks in organic chemistry. It covers their reactivity in various reactions, including cycloadditions, polymerizations, halogenation, hydrohalogenation, and transition-metal-catalyzed reactions. The review provides an overview of the current state of the art and future prospects in the chemistry of vinylpyrazoles.
Article
Biochemistry & Molecular Biology
Karolina Kula et al.
Summary: Experimental and theoretical studies were conducted on the reaction between (E)-3,3,3-trichloro-1-nitroprop-1-ene and N-(4-bromophenyl)-C-arylnitrylimine. The unexpected product, 1-(4-bromophenyl)-3-phenyl-5-nitropyrazole, was formed instead of the expected Delta(2)-pyrazoline molecular system due to a unique CHCl3 elimination process. Theoretical analysis showed favorable kinetic conditions for both possible channels of [3 + 2] cycloaddition, leading to the formation of 1-(4-bromophenyl)-3-aryl-4-tricholomethyl-5-nitro-Delta(2)-pyrazoline. However, the experimental results demonstrated complete regioselectivity in the reactions.
Article
Biochemistry & Molecular Biology
Greta Utecht-Jarzynska et al.
Summary: A solvent-free two-step synthesis of polyfunctionalized pyrazoles under ball-milling mechanochemical conditions was developed, enabling the control of substituents through a unique reaction pathway.
Article
Biochemistry & Molecular Biology
Karolina Dzedulionyte et al.
Summary: A general approach for the synthesis of tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one derivatives was developed. This approach involved a regioselective strategy for synthesizing ethyl 1-(oxiran-2-ylmethyl)-1H-pyrazole-5-carboxylates followed by ring-opening and cyclisation reactions to yield the target compounds. A straightforward two-step method was also applied to functionalize other derivatives. The structures of the fused heterocyclic compounds were confirmed using spectroscopy techniques.
Review
Biochemistry & Molecular Biology
Diana Becerra et al.
Summary: This review summarizes the recent developments in the synthesis of biologically active molecules containing the pyrazole moiety using multicomponent reactions. The review provides analytical and activity data, synthetic mechanisms, and molecular docking simulations for these molecules, in order to facilitate further research in this area.
Article
Biochemistry & Molecular Biology
Matteo Lusardi et al.
Summary: A library of highly functionalized phenylaminopyrazoles was synthesized, characterized, and tested for their cell-based activities, showing potential pharmaceutical applications.
Article
Biochemistry & Molecular Biology
Beatrice Razmiene et al.
Summary: A library of novel 2,4,6,7-tetrasubstituted-2H-pyrazolo[4,3-c]pyridines was synthesized and evaluated for their anticancer activity, with some compounds showing promising antiproliferative effects. Among them, 4-(2,6-diphenyl-2H-pyrazolo[4,3-c]pyridin-7-yl)phenol exhibited potent cell induction activity, along with excellent fluorescence properties, making it a potential pH indicator for pH sensing applications.
Article
Biochemistry & Molecular Biology
Joungmo Cho et al.
Summary: An unusual formation of four-coordinate boron(III) complexes was observed from the reaction of 1-(2-pyridinyl)-5-pyrazolone derivatives with arylboronic acids in basic media. The use of unprotected boronic acid and a bidentate ligand are essential for this transformation. Current experiments are underway to gain a deeper understanding of the mechanism involved.
Article
Biochemistry & Molecular Biology
Abdulrhman Alsayari et al.
Summary: A convenient synthesis of novel pyrazolo[5,1-b]thiazole-based heterocycles was carried out in this study, and the synthesized compounds were characterized and evaluated for antimicrobial and anticancer activities, showing promising results. These products could potentially serve as leading compounds for future drug molecule design.
Article
Biochemistry & Molecular Biology
Vaida Milisiunaite et al.
Summary: A novel synthetic route to pyrazolo[4',3':5,6]pyrano[4,3-c][1,2]oxazole ring systems was developed using intramolecular nitrile oxide cycloaddition reaction. The configuration of intermediate aldoximes was determined using NOESY data and J(CH) coupling constants. The structures of the obtained heterocyclic products were confirmed using H-1, C-13, N-15 NMR spectroscopy and HRMS.
