pyrazoles-derivatives

Quality Control of 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleIn 2016 ,《Design, synthesis and biological evaluation of novel cholesteryl ester transfer protein inhibitors bearing a cycloalkene scaffold》 appeared in European Journal of Medicinal Chemistry. The author of the article were Liu, Chunchi; Luo, Changqun; Hao, Lijuan; Wu, Qiong; Xie, Honglei; Zhao, Shizhen; Hao, Chenzhou; Zhao, Dongmei; Cheng, Maosheng. The article conveys some information:

Cholesteryl ester transfer protein (CETP) is a potential target for cardiovascular disease therapy as inhibition of CETP leads to increased HDL-C in humans. Based on the structure of Merck’s biphenyl CETP inhibitor, authors designed novel N,N-substituted-cycloalkenyl-methylamine scaffold derivatives by utilizing core replacement and conformational restriction strategies. Consequently, twenty-eight compounds were synthesized and evaluated for their inhibitory activity against CETP. Their preliminary structure-activity relationships (SARs) studies indicate that polar substituents were tolerated in moiety A and hydrophobic alkyl groups at the 5-position of cyclohexene were critical for potency. Among them, compound 17a, bearing an N-(5-pyrazolyl-pyrimidin-2-yl)-cycloalkenyl- methylamine scaffold, exhibited excellent CETP inhibitory activity (IC50 = 0.07 μM) in vitro. Furthermore, it showed an acceptable pharmacokinetic profile in S-D rats and efficient HDL-C increase in high-fat fed hamsters. In the part of experimental materials, we found many familiar compounds, such as 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole(cas: 847818-74-0Quality Control 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, neuroleptic, anticonvulsant, monoamine oxidase inhibitory, anti-inflammatory, antipyretic, antiarrhythmic, sedative, muscle relaxant, antidiabetic and antibacterial activities. Quality Control 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

Name: Methyl 1H-pyrazole-3-carboxylateIn 2021 ,《Route Design to Manufacture: Synthesis of the Heterocyclic Fragment of AZD5718 Using a Non-cryogenic Lithiation-Alkoxycarbonylation Reaction》 was published in Organic Process Research & Development. The article was written by Burns, Matthew; Perkins, Dave; Chan, Lai C.; Pilling, Michael J.; Jawor-Baczynska, Anna; Mullen, Alexander K.; Steven, Alan; Wimsey, Chris; Elmekawy, Ahmed; Lamacraft, Alex; Dobson, Benjamin C.; McMillan, Angus E.; Hose, David R. J.; Inglesby, Phillip A.; Raw, Steven A.; Jones, Martin F.. The article contains the following contents:

Route design and process development of the small nitrogen heterocycle I, a constituent of AZD5718 (II), is described. The novel synthetic sequence to I involves a desymmetrizing alkylation of 4-nitropyrazole, a non-cryogenic lithiation-alkoxycarbonylation, and a global reduction-cyclization. This new synthetic route was implemented in the manufacture of I and was able to deliver over 1000 kg of product with a yield of 77% over the three stages. In the experiment, the researchers used many compounds, for example, Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Name: 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.Name: Methyl 1H-pyrazole-3-carboxylate

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

《A Continuous Flow Strategy for the Facile Synthesis and Elaboration of Semi-Saturated Heterobicyclic Fragments》 was published in European Journal of Organic Chemistry in 2019. These research results belong to Luise, Nicola; Wyatt, Eleanor W.; Tarver, Gary J.; Wyatt, Paul G.. Category: pyrazoles-derivatives The article mentions the following:

An efficient hydrogenation protocol under continuous flow conditions was developed for the synthesis of underrepresented semi-saturated bicyclic fragments containing highly sp3-rich skeletons for fragment-based drug discovery (FBDD) programs. Excellent yields were generally achieved by using Pd/C (10% weight/weight) and RaNi at 25-150° under 4-100 bar of hydrogen pressure. The generated fragments, with appropriate physicochem. properties, present diverse hydrogen-bonding pharmacophores and useful vectors for their synthetic elaboration in the optimization stage. Successive, simple functionalizations in continuous flow were accomplished to demonstrate the opportunity to develop multi-step continuous flow synthesis of valuable starting points for FBDD campaigns. A conclusive quality control (QC) was essential to discard those structures which do not fit the typical fragment library parameters. The results came from multiple reactions, including the reaction of Methyl 1H-pyrazolo[4,3-b]pyridine-6-carboxylate(cas: 1301214-72-1Category: pyrazoles-derivatives)

Methyl 1H-pyrazolo[4,3-b]pyridine-6-carboxylate(cas: 1301214-72-1) belongs to pyrazoles. The application of pyrazole derivatives in the development of anticancer agents has been thoroughly investigated and verified. Moreover, the medicinal features of a number of natural products incorporating pyrazole moiety such as pyrazofurin, pyrazofurin B, pyrazole-3(5)-carboxylic acid and 4-methylpyrazole-3(5)-carboxylic acid have been reported.Category: pyrazoles-derivatives

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

《Orchestrated Triple C-H Activation Reactions Using Two Directing Groups: Rapid Assembly of Complex Pyrazoles》 was published in Angewandte Chemie, International Edition in 2015. These research results belong to Yang, Weibo; Ye, Shengqing; Fanning, Dewey; Coon, Timothy; Schmidt, Yvonne; Krenitsky, Paul; Stamos, Dean; Yu, Jin-Quan. Reference of 3-(tert-Butyl)-1-ethyl-1H-pyrazole-5-carboxylic acid The article mentions the following:

A sequential triple C-H activation reaction directed by a pyrazole and an amide group leads to the well-controlled construction of sterically congested dihydrobenzo[e]indazole derivs I [R1 = H, 4-Me, 3-Me, 3,4-diMe, 4-Ph, 4-F, etc.; R2 = Me, (CH2)2Ph, (CH2)3Ph; R3 = Me, Et, iBu, cyclohexylmethyl; R2R3=(CH2)5; R4 = Me, Et]. This cascade reaction demonstrates that the often problematic competing C-H activation pathways in the presence of multiple directing groups can be harvested by design to improve step economy in synthesis. Pyrazole as a relatively weak coordinating group is shown to direct Csp3-H activation for the first time. In the experiment, the researchers used 3-(tert-Butyl)-1-ethyl-1H-pyrazole-5-carboxylic acid(cas: 195447-83-7Reference of 3-(tert-Butyl)-1-ethyl-1H-pyrazole-5-carboxylic acid)

3-(tert-Butyl)-1-ethyl-1H-pyrazole-5-carboxylic acid(cas: 195447-83-7) 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.Reference of 3-(tert-Butyl)-1-ethyl-1H-pyrazole-5-carboxylic acid

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

《Quaternization and dequaternization of pyrazoles in solvent-free conditions: conventional heating versus microwave irradiation》 was written by Diez-Barra, Enrique; De la Hoz, Antonio; Sanchez-Migallon, Ana; Elguero, Jose. Reference of 1-Butyl-1H-pyrazole And the article was included in Journal of Heterocyclic Chemistry on August 31 ,1999. The article conveys some information:

A study on the quaternization and dequaternization of pyrazoles by conventional heating and microwave irradiation in solvent-free conditions is reported. Microwave irradiation produces an acceleration in the quaternization rate and a rapid equilibration between quaternized and non-quaternized products. Dequaternization is also more rapid and a change in the selectivity is observed using sym. pyrazolium salts. The experimental process involved the reaction of 1-Butyl-1H-pyrazole(cas: 52096-24-9Reference of 1-Butyl-1H-pyrazole)

1-Butyl-1H-pyrazole(cas: 52096-24-9) 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.Reference of 1-Butyl-1H-pyrazole

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

《Versatile Tri(pyrazolyl)phosphanes as Phosphorus Precursors for the Synthesis of Highly Emitting InP/ZnS Quantum Dots》 was written by Panzer, Rene; Guhrenz, Chris; Haubold, Danny; Huebner, Rene; Gaponik, Nikolai; Eychmueller, Alexander; Weigand, Jan J.. Synthetic Route of C4H3F3N2This research focused ontripyrazolyl phosphane phosphorus indium phosphide zinc sulfide QD; hot injection; oleylamine; phosphorus; quantum dots; waste prevention. The article conveys some information:

Tri(pyrazolyl)phosphanes (5R1,R2) are utilized as an alternative, cheap and low-toxic phosphorus source for the convenient synthesis of InP/ZnS quantum dots (QDs). From these precursors, remarkably long-term stable stock solutions (>6 mo) of P(OLA)3 (OLAH=oleylamine) are generated from which the resp. pyrazoles are conveniently recovered. P(OLA)3 acts simultaneously as phosphorus source and reducing agent in the synthesis of highly emitting InP/ZnS core/shell QDs. These QDs are characterized by a spectral range between 530-620 nm and photoluminescence quantum yields (PL QYs) between 51-62 %. A proof-of-concept white light-emitting diode (LED) applying the InP/ZnS QDs as a color-conversion layer was built to demonstrate their applicability and processibility. In the experimental materials used by the author, we found 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

Computed Properties of C9H9N3O2On September 8, 2016 ,《Discovery of a Selective Phosphoinositide-3-Kinase (PI3K)-γ Inhibitor (IPI-549) as an Immuno-Oncology Clinical Candidate》 was published in ACS Medicinal Chemistry Letters. The article was written by Evans, Catherine A.; Liu, Tao; Lescarbeau, Andre; Nair, Somarajan J.; Grenier, Louis; Pradeilles, Johan A.; Glenadel, Quentin; Tibbitts, Thomas; Rowley, Ann M.; DiNitto, Jonathan P.; Brophy, Erin E.; OHearn, Erin L.; Ali, Janid A.; Winkler, David G.; Goldstein, Stanley I.; OHearn, Patrick; Martin, Christian M.; Hoyt, Jennifer G.; Soglia, John R.; Cheung, Culver; Pink, Melissa M.; Proctor, Jennifer L.; Palombella, Vito J.; Tremblay, Martin R.; Castro, Alfredo C.. The article contains the following contents:

Optimization of isoquinolinone PI3K inhibitors led to the discovery of a potent inhibitor of PI3K-γ (IPI-549) with >100-fold selectivity over other lipid and protein kinases. IPI-549 demonstrates favorable pharmacokinetic properties and robust inhibition of PI3K-γ mediated neutrophil migration in vivo and is currently in Phase 1 clin. evaluation in subjects with advanced solid tumors. After reading the article, we found that the author used Methyl 2-aminopyrazolo[1,5-a]pyridine-3-carboxylate(cas: 1620075-73-1Computed Properties of C9H9N3O2)

Methyl 2-aminopyrazolo[1,5-a]pyridine-3-carboxylate(cas: 1620075-73-1) 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. Computed Properties of C9H9N3O2

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

Abu Talip, Ruwaida Asyikin; Yahya, Wan Zaireen Nisa; Bustam, Mohamad Azmi published an article on January 15 ,2022. The article was titled 《Understanding the physicochemical and transport properties of pyrazolium based ionic liquids bearing iodide and triiodide anions》, and you may find the article in Journal of Molecular Liquids.Reference of 1-Methylpyrazole The information in the text is summarized as follows:

Ionic liquids (ILs) particularly imidazolium-based ILs have been widely used in various industrial applications such as solvent or catalyst for synthesis, as electrolyte in energy devices, and as solvent for extraction and separation The extensive phys. and chem. properties data available on the imidazolium-based ILs have made them easier to be incorporated into variety of applications compared to other types of ionic liquids Ionic liquids composed of pyrazolium derivative as cation having the same heteroaromatic ring structure with imidazolium derivative except for the position of the nitrogen atoms, may result in unique phys. and chem. properties, yet have been minimally explored. The main objective of this study is to investigate the physicochem. and transport properties of pyrazolium-based ILs to fully comprehend their potential for further development for a specific task or application. In this study, three alkylpyrazolium iodides ILs as well as corresponding three alkylpyrazolium triiodides ILs were synthesized and characterized. The NMR anal. showed that the formation of alkylpyrazolium triiodides ILs from their resp. iodide precursors has resulted the resonance to be more deshielded due to lesser electron d. experienced by the acidic protons of pyrazolium cation due to the weakly localized charge in triiodide anion. The effect of different anions and the alkyl chain of the pyrazolium cation moiety has a pronounced effect on the phys. and transport properties of the synthesized ILs. It is found that the pyrazolium ionic liquids with triiodide anion demonstrated high thermal stability, low viscosity, and high ionic conductivity as compared to the iodide analogs.1-Methylpyrazole(cas: 930-36-9Reference of 1-Methylpyrazole) was used in this study.

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. Reference of 1-Methylpyrazole

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

Sun, Lingyi; Bera, Hriday; Chui, Wai Keung published an article in European Journal of Medicinal Chemistry. The title of the article was 《Synthesis of pyrazolo[1,5-a][1,3,5]triazine derivatives as inhibitors of thymidine phosphorylase》.Recommanded Product: 4-(4-(tert-Butyl)phenyl)-1H-pyrazol-3-amine The author mentioned the following in the article:

Thymidine phosphorylase (TP) is an enzyme that promotes tumor growth and metastasis and therefore is an attractive druggable target. Using a reported TP inhibitor, 7-deazaxanthine (7DX), as the lead compound; this study was set up to evaluate whether pyrazolo[1,5-a][1,3,5]triazin-2,4-diones and pyrazolo[1,5-a][1,3,5]triazin-2-thioxo-4-ones would exhibit TP inhibitory activity. The pyrazolo[1,5-a][1,3,5]triazine nucleus was constructed using a reaction that annulated the 1,3,5-triazine ring onto a pyrazole scaffold. Among the 52 compounds synthesized and tested, it was found that 1,3-dihydro-pyrazolo[1,5-a][1,3,5]triazin-2-thioxo-4-ones exhibited various extent of inhibitory activity against TP. The best compound I, which bears a para-substituted pentafluorosulfur group, showed an IC50 value of 0.04 μM, which was around 800 times more potent than the 7DX (IC50 = 32 μM) under the same bioassay conditions. The results of the study suggested that a substituent with +σ and +π properties inserted at position 4 of a Ph ring that is attached to position 8 of the pyrazolo[1,5-a][1,3,5]triazin-2-thioxo-4-one scaffold would give excellent TP inhibitory action. In addition, I was found to be a non-competitive inhibitor thus suggested that it might interact with TP at a position different from the substrate binding site. In the experimental materials used by the author, we found 4-(4-(tert-Butyl)phenyl)-1H-pyrazol-3-amine(cas: 1015845-73-4Recommanded Product: 4-(4-(tert-Butyl)phenyl)-1H-pyrazol-3-amine)

4-(4-(tert-Butyl)phenyl)-1H-pyrazol-3-amine(cas: 1015845-73-4) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Recommanded Product: 4-(4-(tert-Butyl)phenyl)-1H-pyrazol-3-amine

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

Wang, Tengfei; Zheng, Danning; Zhang, Jingshun; Fan, Baowan; Ma, Yuan; Ren, Tiegang; Wang, Li; Zhang, Jinglai published an article on February 5 ,2018. The article was titled 《Protic Pyrazolium Ionic Liquids: An Efficient Catalyst for Conversion of CO2 in the Absence of Metal and Solvent》, and you may find the article in ACS Sustainable Chemistry & Engineering.Safety of 1-Butyl-1H-pyrazole The information in the text is summarized as follows:

A series of novel protic pyrazolium ionic liquids are firstly synthesized and utilized as catalysts for cycloaddition of carbon dioxide and epoxides to form cyclic carbonates under metal- and solvent-free conditions. The new developed protic pyrazolium ionic liquids present excellent catalytic activity towards the fixation of carbon dioxide. More importantly, they would be prepared by a facile two-step reaction from cheap raw starting materials with a total yield more than 90%. The influence of catalyst dosage, reaction temperature, carbon dioxide pressure, and reaction time on the synthesis of cyclic carbonates is studied to identify the optimal reaction conditions. Under the optimum condition, the catalyst suitability is studied. Addnl., the possible reaction mechanism is studied by the Double-IL model to elucidate the synergistic effects of electrostatic and weak interaction in catalytic process. The experimental process involved the reaction of 1-Butyl-1H-pyrazole(cas: 52096-24-9Safety of 1-Butyl-1H-pyrazole)

1-Butyl-1H-pyrazole(cas: 52096-24-9) 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. Safety of 1-Butyl-1H-pyrazole

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