Category: pyrazoles-derivatives

Kudashev, Anton; Baudoin, Olivier published their research in Chemistry – A European Journal on December 15 ,2021. The article was titled 《Site-Selective Pd-Catalyzed C(sp3)-H Arylation of Heteroaromatic Ketones》.Related Products of 930-36-9 The article contains the following contents:

A ligand-controlled site-selective C(sp3)-H arylation of heteroaromatic ketones had been developed using Pd catalysis to gave ArC(O)CHR1CH2R2 [Ar = thiazol-2-yl, 2-pyridyl, 2-quinolyl, etc.; R1 = Ph, 4-MeC6H4, 2-naphthyl, etc.; R2 = H, Me, ph, etc.]. The reaction occurred selectively at the α- or β-position of the ketone side-chain. The switch from α- or β-arylation was realized by addition of a pyridone ligand. The α-arylation process showed broad scope and high site- and chemoselectivity, whereas the β-arylation was more limited. Mechanistic investigations suggested that α-arylation occurs through C-H activation/oxidative addition/reductive elimination whereas β-arylation involves desaturation and aryl insertion. After reading the article, we found that the author used 1-Methylpyrazole(cas: 930-36-9Related Products of 930-36-9)

1-Methylpyrazole(cas: 930-36-9) belongs to pyrazoles. Pyrazoles and their related multiring analogs are common elements of a wide variety of bioactive compounds. These ring structures are rare in nature. A consequence of this is that they have previously been thought to be poor moieties to include in potential new drugs. Related Products of 930-36-9

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

In 2016,Advanced Synthesis & Catalysis included an article by Alam, Khyarul; Kim, Seong Min; Kim, Do Joong; Park, Jin Kyoon. Application of 80537-07-1. The article was titled 《Development of Structurally Diverse N-Heterocyclic Carbene Ligands via Palladium-Copper-Catalyzed Decarboxylative Arylation of Pyrazolo[1,5-a]pyridine-3-carboxylic Acid》. The information in the text is summarized as follows:

A series of fused non-classical normal N-heterocyclic carbenes, Pyrpy-NHC precursors derived from pyrazolo[1,5-a]pyridines, has been prepared using palladium-copper-catalyzed decarboxylative arylation of pyrazolo[1,5-a]pyridine-3-carboxylic acid. Air-stable palladium and rhodium complexes of these ligands have been synthesized via mild transmetalation of Ag-Pyrpy-NHC. The structural properties of Rh(Pyrpy-NHC)(COD)Cl complexes were determined via X-ray anal. The measurement of the CO stretching frequencies of dicarbonyl Rh-Pyrpy-NHC complexes revealed that the electron donating strength of Pyrpy-NHC could be tuned by varying the substituents of the aryl group. A catalytic study of the Pd-Pyrpy-NHC complexes revealed promising activity in the Suzuki-Miyaura reaction under ambient atm. conditions. The experimental part of the paper was very detailed, including the reaction process of 2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid(cas: 80537-07-1Application of 80537-07-1)

2-Phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid(cas: 80537-07-1) belongs to pyrazoles. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, antipyretic, neuroleptic, anticonvulsant, antiarrhythmic, sedative, muscle relaxant, monoamine oxidase inhibitory, anti-inflammatory, antidiabetic and antibacterial activities. Application of 80537-07-1

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

Hayashi, Hiroki; Takano, Hideaki; Katsuyama, Hitomi; Harabuchi, Yu; Maeda, Satoshi; Mita, Tsuyoshi published an article in Chemistry – A European Journal. The title of the article was 《Synthesis of difluoroglycine derivatives from amines, difluorocarbene, and CO2: computational design, scope, and applications》.Application In Synthesis of 1-Methylpyrazole The author mentioned the following in the article:

A three-component reaction (3CR) for the synthesis of difluoroglycine derivatives has been achieved by using amines, difluorocarbene (generated in situ), and the abundant, inexpensive, and nontoxic C1 source CO2. Various tert-amines and pyridine, (iso)quinoline, imidazole, thiazole, and pyrazole derivatives were incorporated, and the corresponding products were isolated in solid form without purification by column chromatog. on silica gel. Detailed reaction profiles of the 3CR were obtained from computational anal. using DFT calculations, and the results critically suggest that simple ammonia is not applicable to this reaction. In addition, as strongly supported by computational predictions, a new reagent that can generate difluorocarbene at 0°C without any additives was discovered. Finally, radical substitution reactions of the obtained difluoroglycine derivatives under photoredox conditions, as well as a synthetic application as an N-heterocyclic carbene ligand are shown. After reading the article, we found that the author used 1-Methylpyrazole(cas: 930-36-9Application In Synthesis of 1-Methylpyrazole)

1-Methylpyrazole(cas: 930-36-9) belongs to pyrazoles. Pyrazoles and their related multiring analogs are common elements of a wide variety of bioactive compounds. These ring structures are rare in nature. A consequence of this is that they have previously been thought to be poor moieties to include in potential new drugs. Application In Synthesis of 1-Methylpyrazole

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

《Synthesis and properties of N-vinyl-3-and N-vinyl-5-pyrazolecarboxylic esters》 was written by Attaryan, H. S.; Grigoryan, A. J.; Panossyan, G. A.; Matsoyan, S. G.. Recommanded Product: Methyl 1H-pyrazole-3-carboxylateThis research focused onvinyl pyrazolecarboxylic ester synthesis radical polymerization copolymerization. The article conveys some information:

Esterification of pyrazolecarboxylic acid by aliphatic alcs. ROH (R=CH3, C2H5,iso-C3H7, C4H9) leads to the formation of corresponding esters; vinylation of the esters in the presence of mercury sulfate leads to the formation of N-vinyl-3- and N-vinyl-5-pyrazolecarboxylic acids. Polymerization and homopolymerization of the obtained monomers in the presence of a radical initiator was studied. In both cases, N-vinyl-5-pyrazolecarboxylic acid is more active. The reactivity ratios in polymerization for Me esters were calculate r1=0.71 and r2=2.7.Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Recommanded Product: Methyl 1H-pyrazole-3-carboxylate) was used in this study.

Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4) belongs to pyrazoles. Pyrazole derivatives have been reported to exhibit a wide range of applications in medicinal chemistry and pharmacology. A large number of drugs incorporating pyrazole structure have been utilized as partial agonists for nicotinic acid receptors, antidepressants, antimicrobial agents, antiviral agents, and antifungal agents solely or along with the combination of other structural motifs.Recommanded Product: Methyl 1H-pyrazole-3-carboxylate

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

《Novel Quinazolinone Inhibitors of ALK2 Flip between Alternate Binding Modes: Structure-Activity Relationship, Structural Characterization, Kinase Profiling, and Cellular Proof of Concept》 was written by Hudson, Liam; Mui, James; Vazquez, Santiago; Carvalho, Diana M.; Williams, Eleanor; Jones, Chris; Bullock, Alex N.; Hoelder, Swen. Quality Control of 4-Bromo-5-cyclopropyl-1H-pyrazole And the article was included in Journal of Medicinal Chemistry on August 23 ,2018. The article conveys some information:

Structure-activity relationship and crystallog. data revealed that quinazolinone-containing fragments flip between two distinct modes of binding to activin receptor-like kinase-2 (ALK2). We explored both binding modes to discover potent inhibitors and characterized the chem. modifications that triggered the flip in binding mode. We report kinase selectivity and demonstrate that compounds of this series modulate ALK2 in cancer cells. These inhibitors are attractive starting points for the discovery of more advanced ALK2 inhibitors. In the part of experimental materials, we found many familiar compounds, such as 4-Bromo-5-cyclopropyl-1H-pyrazole(cas: 957345-28-7Quality Control of 4-Bromo-5-cyclopropyl-1H-pyrazole)

4-Bromo-5-cyclopropyl-1H-pyrazole(cas: 957345-28-7) belongs to pyrazoles. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, antipyretic, neuroleptic, anticonvulsant, antiarrhythmic, sedative, muscle relaxant, monoamine oxidase inhibitory, anti-inflammatory, antidiabetic and antibacterial activities. Quality Control of 4-Bromo-5-cyclopropyl-1H-pyrazole

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

《1,2,3-Triazines. IV. Synthesis of 1,2,3-triazinecarboxylates》 was written by Neunhoeffer, Hans; Bopp, Ralf; Diehl, Werner. Safety of Methyl 1H-pyrazole-3-carboxylateThis research focused ontriazine preparation; triazinecarboxylate preparation; rearrangement cyclopropenyl azide; pyrazolotriazinone preparation; ring expansion pyrazolamine alkoxycarbonyl; aminopyrazole alkoxycarbonyl ring enlargement. The article conveys some information:

Some 1,2,3-triazinecarboxylates I ((R = Me, ethyl; R1 = aryl; R2 = aryl, trimethylsilyl) were prepared by rearrangement of intermediate (alkoxycarbonyl)cyclopropenyl azides II (same R, R1, R2) as well as by oxidation of 1-aminopyrazoles. Reaction of 1-aminopyrazole-5-carboxylates with tri-Et orthoformate and ammonia gave pyrazolo[3,2-f][1,2,4]triazin-4-ones. The results came from multiple reactions, including the reaction of Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Safety of Methyl 1H-pyrazole-3-carboxylate)

Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4) belongs to pyrazoles. Pyrazole derivatives have been reported to exhibit a wide range of applications in medicinal chemistry and pharmacology. A large number of drugs incorporating pyrazole structure have been utilized as partial agonists for nicotinic acid receptors, antidepressants, antimicrobial agents, antiviral agents, and antifungal agents solely or along with the combination of other structural motifs.Safety of Methyl 1H-pyrazole-3-carboxylate

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

Formula: C10H17BN2O2In 2017 ,《A novel and efficient route for synthesis of Taladegib》 was published in Journal of Chemical Research. The article was written by Guo, Mingliang; Hong, Kwon Ho; Lv, Yongfeng; Ding, Yu; Li, Congcong; Xu, Hua; Qi, Wenxiu; Chen, Junqing; Ji, Min; Cai, Jin. The article contains the following contents:

Taladegib (LY-2940680), a small mol. Hedgehog signaling pathway inhibitor, was obtained from N-benzyl-4-piperidone via Borch reductive amination, acylation with 4-fluoro-2-(trifluoromethyl)benzoyl chloride, debenzylation, substitution with 1,4-dichlorophthalazine and Suzuki cross-coupling reaction with 1-methyl-1H-pyrazole-5-boronic acid. The advantages of this synthesis route were the elimination of Boc protection and deprotection and the inexpensive starting materials. Furthermore, the debenzylation reaction was achieved with simplified operational procedure using ammonium formate as hydrogen source that provided high reaction yield. This synthetic procedure was suitable for large-scale production of the compound for biol. evaluation and further study. The results came from multiple reactions, including the reaction of 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(cas: 847818-74-0Formula: C10H17BN2O2)

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(cas: 847818-74-0) belongs to pyrazoles. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, antipyretic, neuroleptic, anticonvulsant, antiarrhythmic, sedative, muscle relaxant, monoamine oxidase inhibitory, anti-inflammatory, antidiabetic and antibacterial activities. Formula: C10H17BN2O2

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

In 2017,Duret, Guillaume; Quinlan, Robert; Yin, Boyang; Martin, Rainer E.; Bisseret, Philippe; Neuburger, Markus; Gandon, Vincent; Blanchard, Nicolas published 《Intramolecular Inverse Electron-Demand [4 + 2] Cycloadditions of Ynamides with Pyrimidines: Scope and Density Functional Theory Insights》.Journal of Organic Chemistry published the findings.Application In Synthesis of 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole The information in the text is summarized as follows:

4-Aminopyridines are valuable scaffolds for the chem. industry in general, from life sciences to catalysis. We report herein a collection of structurally diverse polycyclic fused and spiro-4-aminopyridines that are prepared in only three steps from com. available pyrimidines. The key step of this short sequence is a [4 + 2]/retro-[4 + 2] cycloaddition between a pyrimidine and an ynamide, which constitutes the first examples of ynamides behaving as electron-rich dienophiles in [4 + 2] cycloaddition reactions. In addition, running the ihDA/rDA reaction in continuous mode in superheated toluene, to overcome the limited scalability of MW reactions, results in a notable production increase compared to batch mode. Finally, d. functional theory investigations shed light on the energetic and geometric requirements of the different steps of the ihDA/rDA sequence. The experimental process involved the reaction of 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(cas: 847818-74-0Application In Synthesis of 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole)

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(cas: 847818-74-0) belongs to pyrazoles. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, monoamine oxidase inhibitory, anti-inflammatory, antipyretic, neuroleptic, anticonvulsant, antiarrhythmic, sedative, muscle relaxant, antidiabetic and antibacterial activities. Application In Synthesis of 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

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

In 2016,Zhang, Xiaojun; Glunz, Peter W.; Johnson, James A.; Jiang, Wen; Jacutin-Porte, Swanee; Ladziata, Vladimir; Zou, Yan; Phillips, Monique S.; Wurtz, Nicholas R.; Parkhurst, Brandon; Rendina, Alan R.; Harper, Timothy M.; Cheney, Daniel L.; Luettgen, Joseph M.; Wong, Pancras C.; Seiffert, Dietmar; Wexler, Ruth R.; Priestley, E. Scott published 《Discovery of a Highly Potent, Selective, and Orally Bioavailable Macrocyclic Inhibitor of Blood Coagulation Factor VIIa-Tissue Factor Complex》.Journal of Medicinal Chemistry published the findings.Recommanded Product: 847818-74-0 The information in the text is summarized as follows:

Inhibitors of the tissue factor (TF)/factor VIIa complex (TF-FVIIa) are promising novel anticoagulants, which show excellent efficacy and minimal bleeding in preclin. models. Starting with an aminoisoquinoline P1-based macrocyclic inhibitor, optimization of the P’ groups led to a series of highly potent and selective TF-FVIIa inhibitors, which displayed poor permeability. Fluorination of the aminoisoquinoline reduced the basicity of the P1 group and significantly improved permeability. The resulting lead compound I was highly potent, selective, and achieved good pharmacokinetics in dogs with oral dosing. Moreover, it demonstrated robust antithrombotic activity in a rabbit model of arterial thrombosis. The experimental part of the paper was very detailed, including the reaction process of 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(cas: 847818-74-0Recommanded Product: 847818-74-0)

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(cas: 847818-74-0) belongs to pyrazoles. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, monoamine oxidase inhibitory, anti-inflammatory, antipyretic, neuroleptic, anticonvulsant, antiarrhythmic, sedative, muscle relaxant, antidiabetic and antibacterial activities. Recommanded Product: 847818-74-0

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

In 2015,Sato, Kenjiro; Takahagi, Hiroki; Kubo, Osamu; Hidaka, Kousuke; Yoshikawa, Takeshi; Kamaura, Masahiro; Nakakariya, Masanori; Amano, Nobuyuki; Adachi, Ryutaro; Maki, Toshiyuki; Take, Kazumi; Takekawa, Shiro; Kitazaki, Tomoyuki; Maekawa, Tsuyoshi published 《Optimization of a novel series of N-phenylindoline-5-sulfonamide-based acyl CoA:monoacylglycerol acyltransferase-2 inhibitors: Mitigation of CYP3A4 time-dependent inhibition and phototoxic liabilities》.Bioorganic & Medicinal Chemistry published the findings.Synthetic Route of C4H3F3N2 The information in the text is summarized as follows:

Acyl CoA:monoacylglycerol acyltransferase-2 (MGAT2) has emerged as a potential peripheral target for the treatment of obesity and metabolic disorders. We previously identified a novel series of N-phenylindoline-5-sulfonamide derivatives exemplified by 2 as potent and orally bioavailable MGAT2 inhibitors. Despite its attractive potency, further assessment revealed that this compound exhibited time-dependent inhibition (TDI) of cytochrome P 450 3A4 (CYP3A4). To remove the undesirable CYP3A4 TDI activity, structural modification was focused on the 2,4-difluoroaniline moiety on the basis of the assumption that this moiety would be involved in mechanism-based inhibition of CYP3A4 via oxidative metabolism This led to the finding that the introduction of 4-chloro-2,6-difluoroaniline significantly improved CYP3A4 TDI risk. Further optimization resulted in the discovery of N-(4-chloro-2,6-difluorophenyl)-1-{5-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]pyrimidin-2-yl}-7-(2-oxopyrrolidin-1-yl)-2,3-dihydro-1H-indole-5-sulfonamide (27c) with potent MGAT2 inhibitory activity (IC50 = 7.8 nM) and excellent ADME-Tox profiles including metabolic stability, oral bioavailability, and CYP3A4 TDI. In a mouse oral fat tolerance test, compound 27c effectively and dose-dependently suppressed the elevation of plasma triacylglycerol levels after oral administration at doses of 1 and 3 mg/kg. We also discuss mitigation of the phototoxic liability of biaryl derivatives on the basis of the HOMO-LUMO gap hypothesis during the course of optimization efforts. The experimental part of the paper was very detailed, including the reaction process of 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Synthetic Route of C4H3F3N2)

3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4) belongs to pyrazoles. Pyrazole derivatives have been reported to exhibit a wide range of applications in medicinal chemistry and pharmacology. A large number of drugs incorporating pyrazole structure have been utilized as partial agonists for nicotinic acid receptors, antidepressants, antimicrobial agents, antiviral agents, and antifungal agents solely or along with the combination of other structural motifs.Synthetic Route of C4H3F3N2

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