Day: February 7, 2023

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

Crystal structure of hexakis(μ₂-chloro)-μ₄-oxo-tetrakis((3,5-dimethylpyrazole)copper(II)) ethanol tetrasolvate, Cu₄OCl₆(C₅H₈N₂)₄·4C₂H₅OH was written by Jacimovic, Zeljko K.;Leovac, Vukadin M.;Tomic, Zoran D.. And the article was included in Zeitschrift fuer Kristallographie – New Crystal Structures in 2007.COA of Formula: C6H9N3O This article mentions the following:

Crystallog. data and at. coordinates are given. In the tetranuclear copper(II) complex Cu₄OCl₆L₄ where L = 3,5-dimethylpyrazole, four copper atoms [separated by 3.070(2) – 3.198(3) Å] encapsulate central oxygen atom in a distorted tetrahedral arrangement, with the Cu-O bond lengths of 1.903(6) – 1.914(6) Å, and the Cu-O-Cu angles of 107.3(3) – 114.3(3)°. Between each pair of copper atoms, there is a bridging chlorine atom with Cu-Cl1 distances of 2.340(4) – 2.509(3) Å. Closer inspection of the Cu-Cl distances reveals grouping of values around every copper atom in two ‘short’ and one ‘long’ distances. Average values are 2.375 Å and 2.459 Å for eight short and six long Cu-Cl distances, resp. Copper coordination sphere is completed by the 3,5-dimethylpyrazole ligand with Cu-N distances of 1.952(7) – 1.957(9) Å. Coordination polyhedron can be described as a slightly distorted trigonal bipyramid where three chlorine atoms lie in the equatorial positions while the central oxygen and the pyridine nitrogen from pyrazolyl ligand are placed at the axial sites. The structure in general is analogous to the structures of previously described tetranuclear complexes of copper [Cu₄(O)(u-X)₆L₄], where L = ligand containing N, O or P donor and X is halogen. Direct contact between the tetranuclear units is achieved by the N-H… Cl hydrogen bonds. In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5COA of Formula: C6H9N3O).

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) 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. 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.COA of Formula: C6H9N3O

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

The identification a novel, selective, non-steroidal, functional glucocorticoid receptor antagonist was written by Rimland, Joseph;Dunne, Angela;Hunjan, Suchete S.;Sasse, Rosemary;Uings, Iain;Montanari, Dino;Caivano, Matilde;Shah, Poonam;Standing, David;Gray, David;Brown, David;Cairns, William;Trump, Ryan;Smith, Paul W.;Bertheleme, Nicolas;D’Alessandro, Pier;Gul, Sheraz;Vimal, Mythily;Smith, David N.;Watson, Stephen P.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.SDS of cas: 3528-58-3 This article mentions the following:

The identification of novel, potent, non-steroidal/small mol. functional GR antagonist GSK1564023A (I) selective over PR is described. Associated structure-activity relationships and the process of optimization of an initial HTS hit are also described. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3SDS of cas: 3528-58-3).

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

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

New potential antitumor pyrazole derivatives: synthesis and cytotoxic evaluation was written by Nitulescu, George Mihai;Draghici, Constantin;Olaru, Octavian Tudorel. And the article was included in International Journal of Molecular Sciences in 2013.HPLC of Formula: 3528-58-3 This article mentions the following:

New pyrazole derivatives I (R¹ = Cl, CH₃; R² = H, CH₃; R³ = C₂H₅, C₆H₅; etc.) were designed and synthesized as potential protein kinase inhibitors in the view to develop specific antitumor therapies. The antitumor potential was estimated using wheat seeds and the general toxicity was evaluated by alternative methods, using invertebrate animals. One 3-aminopyrazole derivative II emerged as a potential candidate for the development of future cytotoxic compounds In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3HPLC of Formula: 3528-58-3).

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

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

Volatile compounds formed by thermal degradation of ascidian tunic carotenoids was written by Choi, Byeong-Dae;Ho, Chi-Tang. And the article was included in Han’guk Nonghwa Hakhoechi in 1997.Electric Literature of C6H9N3O This article mentions the following:

As part of investigation for utilization of ascidian tunic carotenoids as a food color additives, the authors attempted to collect the volatile thermal degradation compounds from ascidian tunic carotenoids. Compounds were extracted by simultaneous distillation and extraction/concentration apparatus and analyzed by gas chromatog. and mass spectrometry. A total of 63 compounds were identified and some of them arose by thermal degradation They included 1,3,5-trimethylbenzene, 3,5,5-trimethyl-3-cyclohexen-1-ol, 3,5,5-trimethyl-3-cyclohexen-1-one, 1,1,2,3-tetramethyl-2-cyclohexen-5-ol, 1,1,2,3-tetramethyl-2-cyclohexen-5-one, 2,3,4,4-tetramethyl-6-hydroxy-2-cyclohexene-1-one, 1,2,3,8-tetrahydro-3,3,6-trimethyl-1-naphthol, dihydroacetinidolide, β-ionone, 2-(1,1,5-trimethyl-3-hydroxy-5-cyclohexen-6-yl)-1-tolylethene, and 2,6-dimethyl-8-(1,1,5-trimethyl-3-hydroxy-5-cyclohexen-6-yl)-1,3,5-octatriene-7-yne. Proposed mechanisms of formation of some compounds as thermal degradation products of ascidian tunic carotenoids are provided. In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Electric Literature of C6H9N3O).

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.Electric Literature of C6H9N3O

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

N,N-dimethylformamide catalyzed electrophilic/nucleophilic chlorination of pyrazoles was written by Liu, Yuanyuan;Li, Yi;Zhang, Zhenglin;Xu, Guanghui;Li, Jie;Gao, Shang. And the article was included in Nanjing Gongye Daxue Xuebao, Ziran Kexueban in 2014.Category: pyrazoles-derivatives This article mentions the following:

With N,N-Dimethylformamide (DMF) as a catalyst, 1-phenyl-5-(p-tolyl)-1H-pyrazol-3-ol (1a) was heated to reflux in thionyl chloride (SOCl₂) and 4-chloro-1-phenyl-5-(p-tolyl)-1H-pyrazol-3-ol (2a) was obtained in the yield of 83%. High performance liquid chromatog. (HPLC) anal. of the reaction mixture revealed that the optimized conditions were n(1a) : n(DMF) of 10:1, and refluxing in SOCl₂ for 4 h. During the column chromatog. purification, elemental sulfur was isolated. The DMF-catalyzed electrophilic/nucleophilic chlorination mechanism was proposed, and pyrazole substrates 1b-1h were prepared to explore the scope of the mechanism. The structures of chlorinated products 2b-2h were characterized by NMR hydrogen spectrum (¹H NMR), NMR carbon spectrum (¹³C NMR), and elemental anal. The structure of 2d was also determined by single-crystal X-ray diffraction anal. This chlorination reaction was simple to be operated and had good functionality tolerance. In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8Category: pyrazoles-derivatives).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. 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.Category: pyrazoles-derivatives

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