pyrazoles-derivatives

Oxidation of pyrazolinones was written by Bischoff, Christian;Ramm, Matthias;Schroeder, Edith;Jancke, Harald. And the article was included in Journal fuer Praktische Chemie/Chemiker-Zeitung in 1994.Computed Properties of C4H5BrN2O This article mentions the following:

Oxidation of pyrazolinones I (R = H, Ph, CONH₂) with H₂O₂/HCOOH gave dimer II which underwent cleavage on treatment with either phenylhydrazine or Br₂ to pyrazolinones III (Q = :NNHPh, Br, resp.). In the experiment, the researchers used many compounds, for example, 4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9Computed Properties of C4H5BrN2O).

4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. The pyrazole ring is resistant to oxidation and reduction but the groups, such as alkyl and formyl attached to the ring, are oxidized to respective acids. Only electrolytic oxidation, ozonolysis, and a strong base cause ring opening.Computed Properties of C4H5BrN2O

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

CO₂ Hydrogenation and Formic Acid Dehydrogenation Using Ir Catalysts with Amide-Based Ligands was written by Kanega, Ryoichi;Ertem, Mehmed Z.;Onishi, Naoya;Szalda, David J.;Fujita, Etsuko;Himeda, Yuichiro. And the article was included in Organometallics in 2020.Formula: C6H9N3O This article mentions the following:

A series of Ir catalysts [Cp*Ir(H₂O)(QCXNHR)][SO₄] (1–16; Q = 2-pyridyl, 4-hydroxy-2-pyridyl, 6-hydroxy-2-pyridyl, 2-imidazolyl, 1-pyrazolyl; X = O, S, NH; R = H, Me, Ph, 4-hydroxyphenyl) bearing amide-based ligands were isolated or generated in situ by a deprotonated amide moiety with the hypotheses that strong electron-donating ability of the coordinated anionic nitrogen atom and the proton-responsive OH group near the metal center will improve the catalytic activity for CO₂ hydrogenation and formic acid (FA) dehydrogenation. The effects of the modifications of the ligand architecture on the catalytic activity were investigated for CO₂ hydrogenation at ambient conditions (25° with 0.1 MPa H₂/CO₂ (volume/volume = 1/1)) and under slightly harsher conditions (50° with 1.0 MPa H₂/CO₂) in basic aqueous solutions together with deuterium kinetic isotope effects (KIEs) with selected catalysts. Complex [Cp*Ir(L12)(H₂O)][HSO₄] (12, L12 = 6-hydroxy-N-phenylpicolinamidate) that has an anionic coordinating N atom and an OH group in the second coordination sphere, exhibits a TOF of 198 h^-1 based on the initial 1 h of reaction. This TOF which, to the best of our knowledge, is the highest value ever reported under ambient conditions in basic aqueous solutions However, complex [Cp*Ir(L10)(H₂O)][HSO₄] (L10 = 4-hydroxy-N-methylpicolinamidate) performs better in long-term CO₂ hydrogenation (up to a TON of 14700 with [Ir] = 10μM after 348 h and the final formate concentration of 0.643 M with [Ir] = 250μM.) at ambient conditions. Further, the catalytic activity for FA dehydrogenation was examined under three different conditions (pH 1.6, 2.3 and 3.5). The complex 12 in any of these conditions is less active compared to the picolinamidate catalysts without ortho-OH, owing to its instability. Theor. calculations were performed to examine the catalytic mechanism, and a step-by-step mechanism has been proposed for both CO₂ hydrogenation and FA dehydrogenation reactions. D. functional theory calculations of [Cp*Ir(L3)(H₂O)][HSO₄] (L3 = picolinamidate) and the X-ray structure of the [Cp*Ir(L7)(H)]•H₂O (L7 = N-methylpicolinamidate) complex imply a pH-dependent conformational change from N,N coordination to N,O coordination upon lowering the pH of the aqueous solution In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Formula: C6H9N3O).

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Formula: C6H9N3O

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

Features of reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with binucleophiles was written by Khachikyan, R. Dzh.;Ovakimyan, Z. G.;Panosyan, G. A.;Tamazyan, R. A.;Ayvazyan, A. G.. And the article was included in Russian Journal of General Chemistry in 2016.Category: pyrazoles-derivatives This article mentions the following:

Reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with hydrazine led to the formation of pyrazole derivatives I•HCl (R = Me, Cl, Br) regardless of pH and a solvent nature. The salts reacted with thiourea via intermediate formation of 4-arylpyrimidine-2-thiol to gave (Z)-2-[(β-aroylvinyl)sulfanyl]-4 arylpyrimidines II (R = Me, Cl, Br). In the case of N,N’-diphenylthiourea the reaction provided 6-aryl-3-aroyl-1-phenylpyridinium bromides III•Br^– (R = Me, Cl, Br). Pyridine hydrobromide liberated in the reaction course had a major influence on the process chemoselectivity. In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Category: pyrazoles-derivatives).

3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9) belongs to pyrazole derivatives. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns.Category: pyrazoles-derivatives

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

Pyrazolo-pyrimidines: A novel heterocyclic scaffold for potent and selective p38α inhibitors was written by Das, Jagabandhu;Moquin, Robert V.;Pitt, Sidney;Zhang, Rosemary;Shen, Ding Ren;McIntyre, Kim W.;Gillooly, Kathleen;Doweyko, Arthur M.;Sack, John S.;Zhang, Hongjian;Kiefer, Susan E.;Kish, Kevin;McKinnon, Murray;Barrish, Joel C.;Dodd, John H.;Schieven, Gary L.;Leftheris, Katerina. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Recommanded Product: 1-Ethyl-1H-pyrazol-3-amine This article mentions the following:

The synthesis and structure-activity relationships (SAR) of p38α MAP kinase inhibitors based on a pyrazolo-pyrimidine scaffold are described. These studies led to the identification of compound I as a potent and selective inhibitor of p38α MAP kinase with excellent cellular potency toward the inhibition of TNFα production I was highly efficacious in vivo in inhibiting TNFα production in an acute murine model of TNFα production X-ray co-crystallog. of a pyrazolopyrimidine analog bound to unphosphorylated p38α is also disclosed. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-3-amine (cas: 55361-49-4Recommanded Product: 1-Ethyl-1H-pyrazol-3-amine).

1-Ethyl-1H-pyrazol-3-amine (cas: 55361-49-4) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.Recommanded Product: 1-Ethyl-1H-pyrazol-3-amine

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

The substituent effects on the chemical shifts of aromatic protons in heterocyclic compounds was written by Liang, Desheng;Lai, Zhugen;Xu, Guanzhi;Jiang, Mingqian. And the article was included in Huaxue Xuebao in 1982.Category: pyrazoles-derivatives This article mentions the following:

The substituent effect on the chem. shifts in ³H NMR of aromatic heterocycles (e.g., furan, thiophene) depended on the electronic effect and the position of the substituents. An empirical formula was derived and the chem. shifts of >700 aromatic protons were calculated to show a deviation of ±0.2-0.3 ppm. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4Category: pyrazoles-derivatives).

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. Pyrazoles and pyrimidines have diverse biological and pharmacological activities. There are a number of antimicrobial compounds containing pyrazole moiety as the core unit. Pyrazofurin is important antimicrobial drug and 2-methylpyrimidine-4-ylamine derivatives I and II were found to be effective inhibitors of Escherichia coli PDHc-E1 with antibacterial and antifungal activity.Category: pyrazoles-derivatives

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

Synthesis and fungitoxicity of derivatives of thiopyrazolone and their oxidation products was written by Devi, S.;Mitra, P.;Mishra, S. B.;Mittra, A. S.. And the article was included in Journal of the Indian Chemical Society in 1983.Quality Control of 4-Bromo-3-methyl-1H-pyrazol-5(4H)-one This article mentions the following:

On treatment with P₂S₅, pyrazolones afford thiopyrazolones which on condensation with 4-monobromo- and dibromopyrazolones in 1:1 and 1:2 ratio, resp., yield mixed bis and tris derivatives, i.e. I and II. The bis compounds of thiopyrazolone were also prepared These compounds with their oxidized derivatives were assayed for antifungal activity against Pyricularia oryzae and Helminthosporium oryzae. Some of the compounds show a very good fungicidal activity and are compared with standard com. fungicides. In the experiment, the researchers used many compounds, for example, 4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9Quality Control of 4-Bromo-3-methyl-1H-pyrazol-5(4H)-one).

4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Quality Control of 4-Bromo-3-methyl-1H-pyrazol-5(4H)-one

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

Penta- and dinuclear carboxylate nickel(II) complexes with pyrazole-based ligands: Syntheses, magnetic properties and DFT calculations was written by Nikiforov, Alexey A.;Dubrov, Evgenii N.;Blinou, Daniil O.;Gurzhiy, Vladislav V.;Selyutin, Artem A.;Klyukin, Ilya N.;Zhdanov, Andrey P.;Minkovich, Alexander E.;Panina, Natalia S.;Eremin, Alexei V.. And the article was included in Polyhedron in 2021.Application In Synthesis of 2-(5-Methyl-1H-pyrazol-3-yl)pyridine This article mentions the following:

<<One pot>> reactions of pyrazole-based ligands Hdmpz and PyPz with in situ formed carboxylate precursors led to the formation of mono- and di-aqua-bridged binuclear compounds, as well as pentanuclear hydroxo-bridged compound: [Ni₂(μ-OH₂)(μ-O₂CC(CH₃)₃)₂(O₂CC(CH₃)₃)₂(PyPz)₂] (1), [Ni₅(μ₃-OH)₂(μ-O₂CPh)₈(PyPz)₄]^.4.73MeCN (2), [Ni₂(μ-OH₂)(μ-O₂CPh)₂(O₂CPh)₂(Hdmpz)₄] (3), [Ni₂(μ-OH₂)₂(μ-O₂CPh)(O₂CPh)₂(Hdmpz)₄](O₂CPh)•2.5H₂O (4) (Hdmpz = 3,5-dimethylpyrazole, PyPz = 2-(5-Methyl-1H-pyrazol-3-yl)pyridine). Compounds were characterized by structural and spectral methods, thermogravimetric anal. and magnetic measurements were also performed. It was noted, that structural motif of forming compounds are determined by the structure of carboxylate precursors formed in situ and properties of N-ligands. Comparison of magnetic measurements data, structural data, and DFT calculations allows us to conclude that in the case of investigated compounds the equilibrium between spin isomers with different multiplicities, close energy values and close geometrical structure (no data) can be realized. In the experiment, the researchers used many compounds, for example, 2-(5-Methyl-1H-pyrazol-3-yl)pyridine (cas: 19959-77-4Application In Synthesis of 2-(5-Methyl-1H-pyrazol-3-yl)pyridine).

2-(5-Methyl-1H-pyrazol-3-yl)pyridine (cas: 19959-77-4) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, anti-inflammatory, antipyretic, antiarrhythmic, sedative, muscle relaxant, neuroleptic, anticonvulsant, monoamine oxidase inhibitory, antidiabetic and antibacterial activities.Application In Synthesis of 2-(5-Methyl-1H-pyrazol-3-yl)pyridine

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

An improved synthesis of 3,6-diamino-1,2,4,5-tetrazine. I was written by Coburn, Michael D.;Ott, Donald G.. And the article was included in Journal of Heterocyclic Chemistry in 1990.Safety of 3,5-Dimethyl-1H-pyrazole-1-carboxamide This article mentions the following:

Treatment of 1,3-diaminoguanidine monohydrochloride with 2,4-pentanedione in alcs. under carefully controlled conditions gave the tetrazine monohydrochloride I in 45-50% yields along with 3,5-dimethyl-1H-pyrazole and its hydrochloride. Oxidation of I with sodium perborate produced 3,6-diamino-1,2,4,5-tetrazine (II) in quant. yield. In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Safety of 3,5-Dimethyl-1H-pyrazole-1-carboxamide).

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. 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. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.Safety of 3,5-Dimethyl-1H-pyrazole-1-carboxamide

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

NVP-BHG712: Effects of Regioisomers on the Affinity and Selectivity toward the EPHrin Family was written by Troester, Alix;Heinzlmeir, Stephanie;Berger, Benedict-Tilman;Gande, Santosh L.;Saxena, Krishna;Sreeramulu, Sridhar;Linhard, Verena;Nasiri, Amir H.;Bolte, Michael;Mueller, Susanne;Kuster, Bernhard;Medard, Guillaume;Kudlinzki, Denis;Schwalbe, Harald. And the article was included in ChemMedChem in 2018.Formula: C5H8N4O This article mentions the following:

Erythropoietin-producing hepatocellular (EPH) receptors are transmembrane receptor tyrosine kinases. Their extracellular domains bind specifically to ephrin A/B ligands, and this binding modulates intracellular kinase activity. EPHs are key players in bidirectional intercellular signaling, controlling cell morphol., adhesion, and migration. They are increasingly recognized as cancer drug targets. We analyzed the binding of NVP-BHG712 (NVP) to EPHA2 and EPHB4. Unexpectedly, all tested com. available NVP samples turned out to be a regioisomer (NVPiso) of the inhibitor, initially described in a Novartis patent application. They only differ by the localization of a single Me group on either one of two adjacent nitrogen atoms. The two compounds of identical mass revealed different binding modes. Furthermore, both in vitro and in vivo experiments showed that the isomers differ in their kinase affinity and selectivity. In the experiment, the researchers used many compounds, for example, 5-Amino-1-methyl-1H-pyrazole-4-carboxamide (cas: 18213-75-7Formula: C5H8N4O).

5-Amino-1-methyl-1H-pyrazole-4-carboxamide (cas: 18213-75-7) belongs to pyrazole derivatives. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. Pyrazoles and pyrimidines have diverse biological and pharmacological activities. There are a number of antimicrobial compounds containing pyrazole moiety as the core unit. Pyrazofurin is important antimicrobial drug and 2-methylpyrimidine-4-ylamine derivatives I and II were found to be effective inhibitors of Escherichia coli PDHc-E1 with antibacterial and antifungal activity.Formula: C5H8N4O

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

Synthesis and fungicidal activity of methyl N-methoxy-N-[2-(3-trifluoromethyl-1-substituted pyrazole-5-yloxymethylene)] phenylcarbamates was written by Liu, Weidong;Li, Jiangsheng;Li, Zhongying;Wang, Xiaoguang;Gao, Bida. And the article was included in Nongyaoxue Xuebao in 2004.Computed Properties of C4H3F3N2O This article mentions the following:

A series of novel Me N-methoxy-N-[2-(3-trifluoromethyl)-1-substituted pyrazole-5-yloxymethylene] phenylcarbamates I (R = Ph, 4-ClPh, 4-FPh, 2-MePh, 2,4-diMePh, 2,4-diClPh, 2-F-4-BrPh, 3,5-DiClPh, 3,4-diClPh, 2,4,5-triClPh, t-Bu, CH₂CO₂Et, Bn) were synthesized from 3-trifluoromethyl-1-substituted pyrazole-5-one and Me N-methoxy-N-(2-bromomethylphenyl) carbamates. All compounds were confirmed by ¹H NMR, IR and LC/MS. The preliminary bioassays showed that some compounds had fungicidal activities to Pyricularia oryzae, Botrytis cinerea, and Erysiphe graminis under 50 mg/L, for example, the inhibitory ratio of compound I (R = Bn) to P. oryzae was 94%. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0Computed Properties of C4H3F3N2O).

3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Computed Properties of C4H3F3N2O

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