269410-08-4 | Page 4 of 10 | pyrazoles-derivatives

Ramachandran, Sreekanth A. team published research in Bioorganic & Medicinal Chemistry Letters in 2017 | 269410-08-4

Safety of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, also known as 4-Pyrazoleboronic acid pinacol ester , is a useful research compound. Its molecular formula is C9H15BN2O2 and its molecular weight is 194.04 g/mol. The purity is usually 95%.

4-Pyrazoleboronic acid pinacol ester is a useful reagent for Suzuki-Miyaura cross-couplings as well as Ruthenium-catalyzed asymmetric hydrogenation. 4-Pyrazoleboronic acid pinacol ester is also a useful reagent for preparing VEGF, Aurora, RHO (ROCK), Janus Kinase 2, c-MET, ALK, S-nitrsoflutathione reductase, CDC7, Acetyl-CoA carboxylase inhibitors.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

4-Pyrazoleboronic acid pinacol ester is an organic compound that is the product of a bifunctional coupling reaction between 4-pyrazolecarboxylic acid and pinacol. It has been shown to inhibit protein S6 kinase, which is involved in the regulation of cell growth and proliferation. This compound has also been shown to be effective against cancer cells, including those that are resistant to conventional chemotherapeutic drugs. 4-Pyrazoleboronic acid pinacol ester may also be used as a precursor for other compounds with pharmaceutical activity., 269410-08-4.

Pyrazoles are synthesized by the reaction of α,β-unsaturated aldehydes with hydrazine and subsequent dehydrogenation. 269410-08-4, formula is C9H15BN2O2, Name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. Substituted pyrazoles are prepared by condensation of 1,3-diketones with hydrazine (Knorr-type reactions). For example, acetylacetone and hydrazine gives 3,5-dimethylpyrazole. Safety of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole.

Ramachandran, Sreekanth A.;Jadhavar, Pradeep S.;Miglani, Sandeep K.;Singh, Manvendra P.;Kalane, Deepak P.;Agarwal, Anil K.;Sathe, Balaji D.;Mukherjee, Kakoli;Gupta, Ashu;Haldar, Srijan;Raja, Mohd.;Singh, Siddhartha;Pham, Son M.;Chakravarty, Sarvajit;Quinn, Kevin;Belmar, Sebastian;Alfaro, Ivan E.;Higgs, Christopher;Bernales, Sebastian;Herrera, Francisco J.;Rai, Roopa research published 《 Design, synthesis and optimization of bis-amide derivatives as CSF1R inhibitors》, the research content is summarized as follows. Signaling via the receptor tyrosine kinase CSF1R is thought to play an important role in recruitment and differentiation of tumor-associated macrophages (TAMs). TAMs play pro-tumorigenic roles, including the suppression of anti-tumor immune response, promotion of angiogenesis and tumor cell metastasis. Because of the role of this signaling pathway in the tumor microenvironment, several small mol. CSF1R kinase inhibitors are undergoing clin. evaluation for cancer therapy, either as a single agent or in combination with other cancer therapies, including immune checkpoint inhibitors. Herein the authors describe the authors’ lead optimization effort that resulted in the identification of a potent, cellular active and orally bioavailable bis-amide CSF1R inhibitor. Docking and biochem. anal. allowed the removal of a metabolically labile and poorly permeable Me piperazine group from an early lead compound Optimization led to improved metabolic stability and Caco2 permeability, which in turn resulted in good oral bioavailability in mice.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Powell, Chelsea E. team published research in ACS Medicinal Chemistry Letters in 2022 | 269410-08-4

269410-08-4, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, also known as 4-Pyrazoleboronic acid pinacol ester , is a useful research compound. Its molecular formula is C9H15BN2O2 and its molecular weight is 194.04 g/mol. The purity is usually 95%.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Pyrazoles and pyrimidines have diverse biological and pharmacological activities. 269410-08-4, formula is C9H15BN2O2, Name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. There are a number of antimicrobial compounds containing pyrazole moiety as the core unit. Application of C9H15BN2O2.

Powell, Chelsea E.;Hatcher, John M.;Jiang, Jie;Vatsan, Prasanna S.;Che, Jianwei;Gray, Nathanael S. research published 《 Selective Macrocyclic Inhibitors of DYRK1A/B》, the research content is summarized as follows. Dual-specificity tyrosine-(Y)-phosphorylation regulated kinase 1A (DYRK1A) is a therapeutic target of interest due to the roles it plays in both neurol. diseases and cancer. We present the development of the first macrocyclic inhibitors of DYRK1A. Initial lead inhibitor JH-XIV-68-3 (3) displayed selectivity for DYRK1A and close family member DYRK1B in biochem. and cellular assays, and demonstrated antitumor efficacy in head and neck squamous cell carcinoma (HNSCC) cell lines. However, we noted that it suffered from rapid aldehyde oxidase (AO)-mediated metabolism To overcome this liability, we generated a derivative (JH-XVII-10 (10)), where fluorine was introduced to block the 2-position of the azaindole and render the mol. resistant to AO activity. We showed that 10 maintains remarkable potency and selectivity in biochem. and cellular assays as well as antitumor efficacy in HNSCC cell lines and improved metabolic stability. Therefore, 10 represents a promising new scaffold for developing DYRK1A-targeting chem. probes and therapeutics.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Prezent, Mikhail A. team published research in ChemistrySelect in 2020 | 269410-08-4

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. 269410-08-4, formula is C9H15BN2O2, Name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C).Pyrazole used as a ligand to prepare organometallic compounds. Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole.

Prezent, Mikhail A.;Baranin, Sergey V. research published 《 Synthesis and Biological Evaluation of New 4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine Derivatives》, the research content is summarized as follows. A number of new spinaceamine derivatives I·HCl (R = Ph, 2,4-difluorophenyl, pyridin-3-yl, etc.) have been synthesized by the Suzuki reaction of 5-Boc-2-iodo-spinaciamine with aryl or heteryl boronic acids RB(OH)₂. The obtained compounds I·HCl exhibited a varying degree of ABTS radical-scavenging activity, and some of them found to be more effective radical-scavengers comparing with spinacine. Both spinacine and its synthesized derivatives I·HCl do not inhibit cholinesterases and carboxylesterase.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Robke, Lucas team published research in Tetrahedron in 2018 | 269410-08-4

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Robke, Lucas;Rodrigues, Tiago;Schroeder, Peter;Foley, Daniel J.;Bernardes, Goncalo J. L.;Laraia, Luca;Waldmann, Herbert research published 《 Discovery of 2,4-dimethoxypyridines as novel autophagy inhibitors》, the research content is summarized as follows. Autophagy is a catabolic process, which mediates degradation of cellular components and has important roles in health and disease. Therefore, small mol. modulators of autophagy are in great demand. Herein, we describe a phenotypic high-content screen for autophagy inhibitors, which led to the discovery of a dimethoxypyridine-based class of autophagy inhibitors, which derive from previously reported, natural product-inspired MAP4K4 inhibitors. Comprehensive structure-activity relationship studies led to a potent compound, and biol. validation experiments indicated that the mode of action was upstream or independent of mTOR.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Rong, Deqin team published research in Journal of Medicinal Chemistry in 2022 | 269410-08-4

Formula: C9H15BN2O2, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, also known as 4-Pyrazoleboronic acid pinacol ester , is a useful research compound. Its molecular formula is C9H15BN2O2 and its molecular weight is 194.04 g/mol. The purity is usually 95%.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Rong, Deqin;Zhou, Kaixin;Fang, Wei;Yang, Hong;Zhang, Yi;Shi, Qiongyu;Huang, Yuting;Li, Jiayi;Dong, Hui;Li, Lanlan;Ding, Jian;Huang, Xun;Wang, Yuanxiang research published 《 Structure-Aided Design, Synthesis, and Biological Evaluation of Potent and Selective Non-Nucleoside Inhibitors Targeting Protein Arginine Methyltransferase 5》, the research content is summarized as follows. PRMT5 is a major type II protein arginine methyltransferase and plays important roles in diverse cellular processes. Overexpression of PRMT5 is implicated in various types of cancer. Many efforts have been made to develop potent and selective PRMT5 inhibitors, the most potent of which is usually derived from nucleoside structures. Here, we designed a novel series of non-nucleoside PRMT5 inhibitors through the structure-aided drug design approach. SAR exploration and metabolic stability optimization led to the discovery of compound 41 as a potent PRMT5 inhibitor with good selectivity. Addnl., compound 41 exerted antiproliferative effects against A375 cells by inducing apoptosis and potently inhibited the methyltransferase activity of PRMT5 in cells. Moreover, it showed attractive pharmacokinetic properties and markedly suppressed the tumor growth in an A375 tumor xenograft model. These results clearly indicate that 41 is a highly potent and selective non-nucleoside PRMT5 inhibitor.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Schubert, Jeffrey W. team published research in ChemMedChem in 2019 | 269410-08-4

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns. 269410-08-4, formula is C9H15BN2O2, Name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. 1-Methyl-5-(trifluoromethyl)pyrazole underwent deprotonation and subsequent carboxylation mainly or exclusively at either the 4-position of the heterocycle or at the nitrogen-attached methyl group. Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole.

Schubert, Jeffrey W.;Harrison, Scott T.;Mulhearn, James;Gomez, Robert;Tynebor, Robert;Jones, Kristen;Bunda, Jaime;Hanney, Barbara;Wai, Jenny Miu-Chen;Cox, Chris;McCauley, John A.;Sanders, John M.;Magliaro, Brian;O’Brien, Julie;Pajkovic, Natasa;Huszar Agrapides, Sarah L.;Taylor, Anne;Gotter, Anthony;Smith, Sean M.;Uslaner, Jason;Browne, Susan;Risso, Stefania;Egbertson, Melissa research published 《 Discovery, optimization, and biological characterization of 2,3,6-trisubstituted pyridine-containing M₄ positive allosteric modulators》, the research content is summarized as follows. Herein we describe the discovery and optimization of a new series of 2,3-disubstituted and 2,3,6-trisubstituted muscarinic acetylcholine receptor 4 (M₄) pos. allosteric modulators (PAMs). Iterative libraries enabled rapid exploration of one-dimensional structure-activity relationships (SAR) and identification of potency-enhancing heterocycle and N-alkyl pyrazole substituents. Further optimization led to identification of the potent, receptor-subtype-selective, brain-penetrant tool compound 24 (7-[3-[1-[(1-fluorocyclopentyl)methyl]pyrazol-4-yl]-6-methyl-2-pyridyl]-3-methoxycinnoline). It is efficacious in preclin. assays that are predictive of antipsychotic effects, producing dose-dependent reversal of amphetamine-induced hyperlocomotion in rats and mice, but not in M₄ knockout mice. Cholinergic-related adverse effects observed in rats treated with 24 at unbound plasma concentrations more than 3-fold higher than an efficacious dose in the hyperlocomotion assay were fewer and less severe than those observed in rats treated with the nonselective M₄ agonist xanomeline, suggesting a receptor-subtype-selective PAM has the potential for an improved safety profile.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Shan, Yuanyuan team published research in European Journal of Medicinal Chemistry in 2019 | 269410-08-4

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Pyrazole is an organic compound with the formula C3H3N2H. It is a heterocycle characterized by a 5-membered ring of three carbon atoms and two adjacent nitrogen atoms, which are in ortho-substitution. 269410-08-4, formula is C9H15BN2O2, Name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. Pyrazoles are a class of compounds that have the ring C3N2 with adjacent nitrogen atoms.Notable drugs containing a pyrazole ring are celecoxib (celebrex) and the anabolic steroid stanozolol. Formula: C9H15BN2O2.

Shan, Yuanyuan;Si, Ru;Wang, Jin;Zhang, Qingqing;Zhou, Huaxin;Song, Jie;Zhang, Jie;Chen, Qinhua research published 《 Discovery of novel anti-angiogenesis agents. Part 9: Multiplex inhibitors suppressing compensatory activations of RTKs》, the research content is summarized as follows. Aberrant angiogenesis is a hallmark of various diseases including cancers. VEGFR-2 inhibitors have been utilized as anti-angiogenic agents for several years. However, compensatory activation of various receptor tyrosine kinases (RTK) could induce the occurrence of resistance. The authors previously reported a series of multi-target inhibitors of VEGFR-2, Tie-2, and EphB4 as anti-angiogenic agents. These inhibitors might be a promising strategy to overcome the resistance induced by compensatory activation. To expand the structural diversity of these multiple RTK inhibitors, the authors described herein the design, synthesis, and evaluation of a novel class of triplet VEGFR-2/TIE-2/EphB4 inhibitors. The biol. evaluation indicated that five compounds exhibited simultaneous VEGFR-2/Tie-2/EphB4 inhibitory activities with IC₅₀ values less than 50 nM.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Pan, Jinpeng team published research in Bioorganic & Medicinal Chemistry in 2019 | 269410-08-4

Related Products of 269410-08-4, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, also known as 4-Pyrazoleboronic acid pinacol ester , is a useful research compound. Its molecular formula is C9H15BN2O2 and its molecular weight is 194.04 g/mol. The purity is usually 95%.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Pan, Jinpeng;Yin, Yan;Zhao, Lianhua;Feng, Yangbo research published 《 Discovery of (S)-6-methoxy-chroman-3-carboxylic acid (4-pyridin-4-yl-phenyl)-amide as potent and isoform selective ROCK2 inhibitors》, the research content is summarized as follows. ROCK1 and ROCK2 are highly homologous isoforms. Accumulated studies indicate that they have distinct different functions, and the development of isoform selective ROCK inhibitors will pave new roads for the treatment of various diseases. In this work, a series of amide-chroman derivatives were synthesized and biol. evaluated in order to develop potent and isoform selective ROCK2 inhibitors. Remarkably, (S)-6-methoxy-chroman-3-carboxylic acid (4-pyridin-4-yl-phenyl)-amide ((S)-7c) possessed ROCK2 inhibitory activity with an IC₅₀ value of 3 nM and 22.7-fold isoform selectivity (vs. ROCK1). Mol. docking indicated that hydrophobic interactions were the key element for the high potency and isoform selectivity of (S)-7c. The binding free energies predicted by MM/GBSA were in good agreement with the exptl. bioactivities, and the anal. of individual energy terms suggested that residue Lys105 in ROCK1 or Lys121 in ROCK2 was the key residue for the isoform selectivity of (S)-7c.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Mosallanejad, Arash team published research in Tetrahedron Letters in 2018 | 269410-08-4

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Mosallanejad, Arash;Lorthioir, Olivier research published 《 Application of Tsunoda reagent to the convenient synthesis of drug-like pyrazoles》, the research content is summarized as follows. The versatility of the under-utilized (cyanomethylene)tributylphosphorane (CMBP, Tsunoda reagent) was demonstrated on two occasions in a drug discovery context. Firstly, the high reactivity of the phosphorane allowed the alkylation of a weakly acidic pyrazole when standard Mitsunobu conditions were unsuccessful. Secondly, the clean reaction profile generally obtained using CMBP allowed the direct use of the crude mixture in a subsequent Suzuki cross coupling. This reagent was utilized when isolation of the Mitsunobu reaction product (e.g. containing a boronate) was not desirable.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Moningka, Remond team published research in Bioorganic & Medicinal Chemistry Letters in 2020 | 269410-08-4

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Moningka, Remond;Romero, F. Anthony;Hastings, Nicholas B.;Guo, Zhiqiang;Wang, Ming;Di Salvo, Jerry;Li, Ying;Trusca, Dorina;Deng, Qiaoling;Tong, Vincent;Terebetski, Jenna L.;Ball, Richard G.;Ujjainwalla, Feroze research published 《 Fragment-based lead discovery of a novel class of small molecule antagonists of neuropeptide B/W receptor subtype 1 (GPR7)》, the research content is summarized as follows. Here, we report the discovery of a new class of NPBWR1 antagonists identified from a fragment-based screen. Compound 1 (cAMP IC₅₀ = 250μM; LE = 0.29) emerged as an initial hit. Further optimization of 1 by SAR-by-catalog and chem. modification produced 21a (cAMP IC₅₀ = 30 nM; LE = 0.39) with a 6700-fold increase in potency from fragment 1. Somewhat surprisingly, Schild anal. of compound 21a suggested that in vitro inhibition of NPW-mediated effects on upon cAMP accumulation were saturable, and that compound 21a dose-dependently increased [125I]-hNPW23 dissociation rate constants from NPBWR1 in kinetic binding studies. Collectively, these data are inconsistent with a classic surmountable, orthosteric mechanism of inhibition. The benzimidazole inhibitors reported herein may therefore represent a mechanistically differentiated class of compounds with which to form a better appreciation of the pharmacol. and physiol. roles of this central neuropeptide system.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics