pyrazoles-derivatives

Transition metal azolates from metallocenes. Part 1: Dimetallic and trimetallic cyclopentadienylnickel pyrazolates, synthesis and structural studies was written by Rettig, Steven J.;Storr, Alan;Summers, David A.;Thompson, Robert C.;Trotter, James. And the article was included in Canadian Journal of Chemistry in 1997.Recommanded Product: 4-Chloro-3,5-dimethyl-1H-pyrazole This article mentions the following:

The reactions of nickelocene with pyrazoles in benzene solution gave either dimeric compounds, [CpNi(μ-pz)]₂, (room temperature conditions) or trimetallic complexes, [CpNi(μ-pz)₂]₂Ni, (elevated temperature conditions). Both dimeric and trimetallic species were obtained as red crystalline materials and x-ray structural studies are reported for representative samples of each type. Structural features are interpreted and compared with similar, previously reported, Ni pyrazolate structures. Crystals of [CpNi(3,5-diMepz)]₂ (C₂₀H₂₄N₄Ni₂), are orthorhombic, a 15.204(1), b 17.967(2), c 6.9786(9) Å, Z = 4, space group Ama2; those of [CpNi(4-NO₂-3,5-diMepz)]₂ (C₂₀H₂₂N₆Ni₂O₂), are orthorhombic, a 17.145(3), b 17.738(1), c 7.006(1) Å, Z = 4, space group P2₁2₁2₁; those of [CpNi(3,5-F₆diMepz)]₂ (C₂₀H₁₂F₁₂N₄Ni₂), are orthorhombic, a 18.7134(8), b 15.619(2), c 7.7263(9) Å, Z = 4, space group Pnma; those of [CpNi(3,5-diMepz)₂]₂Ni (C₃₀H₃₈N₈Ni₃), are triclinic, a 10.078(2), b 16.134(2), c 9.992(1) Å, α 91.586(10), β 111.050(9), γ 86.95(1)°, Z = 2, space group P1; and those of [CpNi(4-Cl-3,5-diMepz)₂]₂Ni (C₃₀H₃₄Cl₄N₈Ni₃), are monoclinic, a 10.2201(7), b 16.174(1), c 10.7207(9) Å, β 108.193(5)°, Z = 2, space group P2₁la. The structures were solved by direct (dimetallic species) or Patterson (trimetallic complexes) methods and were refined by full-matrix least-squares procedures to R = 0.035, 0.032, 0.058, 0.032, and 0.033 (R_w = 0.021, 0.026, 0.053, 0.028, and 0.032) for 1157, 1894, 1642, 4499, and 2113 reflections with I ≥ 3σ(F²), resp. In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8Recommanded Product: 4-Chloro-3,5-dimethyl-1H-pyrazole).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) belongs to pyrazole derivatives. As is the case with imidazoles, the pyrazole ring offers many opportunities to create new multiring systems that incorporate this heterocycle. 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.Recommanded Product: 4-Chloro-3,5-dimethyl-1H-pyrazole

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

One-pot, procedure for the preparation of some thiazino[2,3-b]quinoxaline derivatives was written by Bakavoli, Mehdi;Eshghi, Hossein;Azizollahi, Hamid;Saberi, Sattar;Bazrafshan, Faezeh. And the article was included in Journal of Chemical Research in 2014.SDS of cas: 51395-52-9 This article mentions the following:

An efficient and convenient synthesis of new thiazino[2,3-b]quinoxaline derivatives I (R = CH₃, C₆H₅, 4-MeC₆H₄, etc.) has been developed by employing a one-pot cyclocondensation of several α-haloketones and 3-aminoquinoxaline-2-thiol in acetic acid. A similar reaction with 4-bromo-3-methyl-4,5-dihydro-1H-5-pyrazolone gave a new heterocyclic system, 3-methyl-1,4-dihydropyrazolo[4′,3′:5,6][1,4]thiazino[2,3-b]quinoxaline. In the experiment, the researchers used many compounds, for example, 4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9SDS of cas: 51395-52-9).

4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9) 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. 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.SDS of cas: 51395-52-9

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

The pyrolytic rearrangement of 1-alkynoyl-3-methylpyrazoles: synthesis of pyrazolo[1,5-a]pyridin-5-ols and related compounds was written by Brown, Roger F. C.;Eastwood, Frank W.;Fallon, Gary D.;Lee, Swee Choo;McGeary, Ross P.. And the article was included in Australian Journal of Chemistry in 1994.COA of Formula: C5H7ClN2 This article mentions the following:

Flash vacuum pyrolysis of 1-(2-alkynoyl)-3-methylpyrazoles (e.g., I; R = H, Me, Ph) at 650°/0.03 mm forms pyrazolo[1,5-a]pyridin-5-ols (e.g., II), often in high yield, which may bear substituents at C2, C3 or C7. In the absence of a 3-Me group in the precursor, N-ethynylpyrazoles are formed in low yield. The formation of both types of product is interpreted as involving 3-(N-pyrazolyl)propadienones formed by N1 → N2 migration of the N-alkynoyl group with inversion of the three-carbon chain. The fused-ring structure of 2-methylpyrazolo[1,5-a]pyridin-5-ol was established by x-ray crystallog. of the O-benzoyl derivative In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8COA of Formula: C5H7ClN2).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. 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.COA of Formula: C5H7ClN2

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

Lanthanide pyrazolecarboxylates for OLEDs and bioimaging was written by Utochnikova, Valentina V.;Latipov, Egor V.;Dalinger, Alexander I.;Nelyubina, Yulia V.;Vashchenko, Andrey A.;Hoffmann, Michael;Kalyakina, Alena S.;Vatsadze, Sergey Z.;Schepers, Ute;Brase, Stefan;Kuzmina, Natalia P.. And the article was included in Journal of Luminescence in 2018.Reference of 10199-53-8 This article mentions the following:

Novel materials based on lanthanide complexes with six pyrazolecarboxylates were obtained. They possess high solubility due to the purposeful introduction of the nitrogen heteroatom in α-position to the carboxy-group, and their luminescence quantum yields reach 100%. High absorption and non-toxicity allowed their successful use for bioimaging in cellulo. While the special approach to electron transport enhancement allowed using them as OLED emission materials. In the experiment, the researchers used many compounds, for example, 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8Reference of 10199-53-8).

1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. 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.Reference of 10199-53-8

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

Synthesis of quinazolone and its derivatives as potential fungicides was written by Das, N. B.;Mittra, A. S.. And the article was included in Journal of the Indian Chemical Society in 1979.Computed Properties of C4H5BrN2O This article mentions the following:

Condensation of 4-bromo-2-pyrazolin-5-one with 2-mercapto-3-aryl-4-quinazolones afforded quinazolones I (R = aryl,R¹ = H, Ph). They are fungitoxic against the rice blast pathogen Pyricularia oryzae and brown leaf spot pathogen Helminthosporium oryzae. 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. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. 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.Computed Properties of C4H5BrN2O

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

A general and practical bifunctional cobalt catalytic system for N-heterocycle assembly via acceptorless dehydrogenation was written by Tian, Haitao;Xue, Wenxuan;Wu, Jingtao;Yang, Ziguang;Lu, Hongcheng;Tang, Conghui. And the article was included in Organic Chemistry Frontiers in 2022.Reference of 19959-77-4 This article mentions the following:

A novel and highly-efficient N-heterocycle assembly methodol. catalyzed by a cobalt-N,N-bidentate complex had been established. The cobalt complex was unprecedented, phosphine-free and easily-prepared, and was used in the synthesis of pyrimidines such as I [R = NH₂, Ph; Ar¹ = Ph, 2-MeOC₆H₄, 2-naphthyl, etc.; Ar² = Ph, 2-thienyl, 4-MeC₆H₄, etc.], quinolines such as II [R¹ = H, 8-Me; R² = H, Me; R³ = t-Bu, Ph, 2-naphthyl, etc.], imidazoles III [R⁴ = H, Me; R⁵ = H, Me, Cl; R⁶ = H, Me, Cl; R⁵R⁶ = CH=CH-CH=CH; Ar³ = Ph, 2-MeC₆H₄, 3-ClC₆H₄, etc.], quinoxalines such as IV [R⁷ = H, 5-Me, 6,7-di-Me, 6,7-di-Cl] and indole from readily available alcs. and amines via acceptorless dehydrogenation. More importantly, all N-heterocycles were obtained under nearly identical reaction conditions, which further demonstrated the generality and practicability of the catalytic system. Mechanistically, this cobalt complex formed a catalytic active species upon base treatment and was capable of realizing the alc. AD process via metal-ligand cooperation. In the experiment, the researchers used many compounds, for example, 2-(5-Methyl-1H-pyrazol-3-yl)pyridine (cas: 19959-77-4Reference of 19959-77-4).

2-(5-Methyl-1H-pyrazol-3-yl)pyridine (cas: 19959-77-4) 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.Reference of 19959-77-4

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

Cyclic guanidines: synthesis and antiplatelet activity of 4,6,7,8-tetrahydro-1H-imidazo[1,2-a]pyrazolo[3,4-d]pyrimidin-7-ones and 1,4,6,7,8,9-hexahydropyrazolo[3′,4′:4,5]pyrimido[2,1-c][1,2,4]triazin-7-ones was written by Ferroni, R.;Simoni, D.;Orlandini, P.;Bardi, A.;Franze, G. P.;Guarneri, M.. And the article was included in Arzneimittel-Forschung in 1990.SDS of cas: 18213-75-7 This article mentions the following:

I (R = e.g., Me, Ph, 4-ClC₆H₄, R¹ = Bu, benzyl, or H) and II (R = e.g., Me, Ph, 4-ClC₆H₄) were prepared starting from 5-amino-4-cyano-1-(2,5-dichlorophenyl)pyrazole through a series of reactions. The compounds were tested for inhibition against blood platelet aggregation induced by ADP or collagen. Among the compounds tested I (R = 2,5-dichlorophenyl, R¹ = CH₂Ph), showed the highest activity. An increase in lipophilicity of the substituent was accompanied by an increase in the platelet aggregation inhibitory activity. Structure-activity relations are discussed. In the experiment, the researchers used many compounds, for example, 5-Amino-1-methyl-1H-pyrazole-4-carboxamide (cas: 18213-75-7SDS of cas: 18213-75-7).

5-Amino-1-methyl-1H-pyrazole-4-carboxamide (cas: 18213-75-7) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns.SDS of cas: 18213-75-7

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

Discovery of 6-(Aminomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxamides as Potent, Selective Dipeptidyl Peptidase-4 (DPP4) Inhibitors was written by Meng, Wei;Brigance, Robert P.;Chao, Hannguang J.;Fura, Aberra;Harrity, Thomas;Marcinkeviciene, Jovita;O’Connor, Stephen P.;Tamura, James K.;Xie, Dianlin;Zhang, Yaqun;Klei, Herbert E.;Kish, Kevin;Weigelt, Carolyn A.;Turdi, Huji;Wang, Aiying;Zahler, Robert;Kirby, Mark S.;Hamann, Lawrence G.. And the article was included in Journal of Medicinal Chemistry in 2010.Related Products of 3528-58-3 This article mentions the following:

Continued structure-activity relation (SAR) exploration within our previously disclosed azolopyrimidine containing dipeptidyl peptidase-4 (DPP4) inhibitors led us to focus on an imidazolopyrimidine series in particular. Further study revealed that by replacing the aryl substitution on the imidazole ring with a more polar carboxylic ester or amide, these compounds displayed not only increased DPP4 binding activity but also significantly reduced human ether-a-go-go related gene (hERG) and sodium channel inhibitory activities. Addnl. incremental adjustment of polarity led to permeable mols. which exhibited favorable pharmacokinetic (PK) profiles in preclin. animal species. The active site binding mode of these compounds was determined by x-ray crystallog. as exemplified by amide 24c. A subsequent lead mol. from this series, (+)-6-(aminomethyl)-5-(2,4-dichlorophenyl)-N-(1-ethyl-1H-pyrazol-5-yl)-7-me3 thylimidazo[1,2-a]pyrimidine-2-carboxamide (24s), emerged as a potent, selective DPP4 inhibitor that displayed excellent PK profiles and in vivo efficacy in ob/ob mice. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Related Products of 3528-58-3).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) 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.Related Products of 3528-58-3

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

Excited-State Intramolecular Proton Transfer in Five-Membered Hydrogen-Bonding Systems: 2-Pyridyl Pyrazoles was written by Yu, Wei-Shan;Cheng, Chung-Chih;Cheng, Yi-Ming;Wu, Pei-Chi;Song, Yi-Hwa;Chi, Yun;Chou, Pi-Tai. And the article was included in Journal of the American Chemical Society in 2003.Recommanded Product: 2-(5-Methyl-1H-pyrazol-3-yl)pyridine This article mentions the following:

The excited-state intramol. proton transfer (ESIPT) reaction in five-membered N-H···N hydrogen-bonding systems has been explored through design and syntheses of a series of 5-(2-pyridyl)-1-H-pyrazoles. The ESIPT mechanism was confirmed through spectroscopy, relaxation dynamics, and corresponding methylated analogs. The results demonstrate for the first time a unique system among ESIPT mols., in which ESIPT incorporates an appreciably large energy barrier fine-tuned by the skeletal reorganization. This makes 5-(2-pyridyl)-1-H-pyrazole systems ideal models for probing the reaction potential energy surface. In the experiment, the researchers used many compounds, for example, 2-(5-Methyl-1H-pyrazol-3-yl)pyridine (cas: 19959-77-4Recommanded Product: 2-(5-Methyl-1H-pyrazol-3-yl)pyridine).

2-(5-Methyl-1H-pyrazol-3-yl)pyridine (cas: 19959-77-4) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns.Recommanded Product: 2-(5-Methyl-1H-pyrazol-3-yl)pyridine

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

Discovery of 2-arylamino-4-(1-methyl-3-isopropylsulfonyl-4-pyrazol-amino)pyrimidines as potent anaplastic lymphoma kinase (ALK) inhibitors was written by Zhang, Peilong;Dong, Jiaqiang;Zhong, Boyu;Zhang, Deyi;Jin, Can;Meng, Xuejing;Sun, Desheng;Xu, Xiangyuan;Zhou, Yong;Liang, Zhi;Ji, Minghua;Li, Hailong;Xu, Tao;Song, Guowei;Zhang, Ling;Chen, Gang;Yuan, Hongbin;Shih, Joe;Zhang, Ruihao;Hou, Guojun;Jin, Ying;Yang, Qiong. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.Quality Control of 1-Methyl-3-nitro-1H-pyrazole This article mentions the following:

A new series of 2,4-diamino pyrimidine derivatives with a sulfone-substituted pyrazole right side-chain were discovered as potent anaplastic lymphoma kinase inhibitors. Structure-activity relationship of the left side-chain on Ph substitutions were explored which delivered many potent ALK inhibitors. Among them, I showed favorable pharmacokinetic profiles in rats and dogs together with significant antitumor efficacy in EML4-ALK fusion xenograft model. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1Quality Control of 1-Methyl-3-nitro-1H-pyrazole).

1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1) belongs to pyrazole derivatives. As is the case with imidazoles, the pyrazole ring offers many opportunities to create new multiring systems that incorporate this heterocycle. 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.Quality Control of 1-Methyl-3-nitro-1H-pyrazole

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