20154-03-4 | Page 7 of 14 | pyrazoles-derivatives

Seo, Samuel’s team published research in Journal of Physical Chemistry B in 2014 | CAS: 20154-03-4

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.Electric Literature of C4H3F3N2

In 2014,Seo, Samuel; Quiroz-Guzman, Mauricio; DeSilva, M. Aruni; Lee, Tae Bum; Huang, Yong; Goodrich, Brett F.; Schneider, William F.; Brennecke, Joan F. published 《Chemically Tunable Ionic Liquids with Aprotic Heterocyclic Anion (AHA) for CO2 Capture》.Journal of Physical Chemistry B published the findings.Electric Literature of C4H3F3N2 The information in the text is summarized as follows:

Ionic liquids (ILs) with aprotic heterocyclic anions, or AHAs, can bind CO2 with reaction enthalpies that are suitable for gas separations and without suffering large viscosity increases. In the present work, we have synthesized ILs bearing an alkyl-phosphonium cation with indazolide, imidazolide, pyrrolide, pyrazolide and triazolide-based anions that span a wide range of predicted reaction enthalpies with CO2. Each AHA-based IL was characterized by NMR spectroscopy and their phys. properties (viscosity, glass transition, and thermal decomposition temperature) determined In addition, the influence of substituent groups on the reaction enthalpy was investigated by measuring the CO2 solubility in each IL at pressures between 0 and 1 bar at 22 °C using a volumetric method. The isotherm-derived enthalpies range between -37 and -54 kJ mol-1 of CO2, and these values are in good agreement with computed enthalpies of gas-phase IL-CO2 reaction products from mol. electronic structure calculations The AHA ILs show no substantial increase in viscosity when fully saturated with CO2 at 1 bar. Phase splitting and compositional anal. of one of the IL/H2O and IL/H2O/CO2 systems conclude that protonation of the 2-cyanopyrrolide anion is improbable, and this result was confirmed by the equimolar CO2 absorption in the presence of water. Taking advantage of the tunable binding energy and absence of viscosity increase after the reaction with CO2, AHA ILs are promising candidates for efficient and environmental-friendly absorbents in postcombustion CO2 capture. The experimental process involved the reaction of 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Electric Literature of C4H3F3N2)

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

Sato, Kenjiro’s team published research in Bioorganic & Medicinal Chemistry in 2015 | CAS: 20154-03-4

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)

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

Kaur, Kamalneet’s team published research in Journal of Fluorine Chemistry in 2015 | CAS: 20154-03-4

Synthetic Route of C4H3F3N2In 2015 ,《Trifluoromethylpyrazoles as anti-inflammatory and antibacterial agents: A review》 appeared in Journal of Fluorine Chemistry. The author of the article were Kaur, Kamalneet; Kumar, Vinod; Kumar Gupta, Girish. The article conveys some information:

A review. In the recent past trifluoromethylpyrazoles have gained much attention, particularly as anti-inflammatory and antibacterial agents, in the field of medicinal chem. The location of trifluoromethyl group, specially on 3- or 5-position of pyrazole nucleus, is greatly associated with variation in activity profile of the compounds Therefore, the main objective of this article is to highlight the importance of trifluoromethylpyrazoles as anti-inflammatory and antibacterial agents on a single front. The present review covers the literature from 2000 to 2015 and would certainly be proven as a great help to the medicinal chemists to explore some novel anti-inflammatory and antibacterial agents with better action profiles with minimal side effects. The experimental process involved the reaction of 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Synthetic Route of C4H3F3N2)

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

Kisan Rasal, Nishant’s team published research in Chemistry & Biodiversity in 2021 | CAS: 20154-03-4

3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4) 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.HPLC of Formula: 20154-03-4

Kisan Rasal, Nishant; Bhaskar Sonawane, Rahul; Vijay Jagtap, Sangeeta published their research in Chemistry & Biodiversity in 2021. The article was titled 《Synthesis, Characterization, and Biological Study of 3-Trifluoromethylpyrazole Tethered Chalcone-Pyrrole and Pyrazoline-Pyrrole Derivatives》.HPLC of Formula: 20154-03-4 The article contains the following contents:

The present study illustrates the design and synthesis of new series of 3-trifluoromethylpyrazole tethered chalcone-pyrrole and pyrazoline-pyrrole derivatives All compounds were further screened for in vitro cytostatic activities on full NCI 60 cancer cell lines at National Cancer Institute, USA. Compounds (2E)-3-(1H-pyrrol-2-yl)-1-{4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}prop-2-en-1-one (I) and (2E)-1-{3-methyl-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}-3-(1H-pyrrol-2-yl)prop-2-en-1-one (II) displayed significant antiproliferative activity (Growth Percentage: -77.10 and -92.13, resp. at 10μM concentration) against the UO-31 cell lines from renal cancer and were further selected for assay at 10-fold dilutions of five different concentrations (10-4 to 10-8 M). Both compounds I and II exhibited promising antiproliferative activity (GI50: 1.36 to 0.27μM) against leukemia cancer cell lines HL-60 and RPMI-8226, colon cancer cell lines KM-12; breast cancer cell lines BT-549. Moreover, both compounds I and II were found to be non-cytotoxic (LC50>100) against HL-60, RPMI-8226, and KM-12 cell lines. Remarkably, GI50 values of these two compounds were identified as more promising than sunitinib against most cancer cell lines and in silico study of compounds I and II exemplified the desired ADME properties for drug-likeness as well as tighter interactions with VEGFR-2. Hence, compounds I and II would be good cytotoxic agents after further clin. study. The experimental process involved the reaction of 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4HPLC of Formula: 20154-03-4)

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

Kino, Tatsuhito’s team published research in Journal of Fluorine Chemistry in 2010 | CAS: 20154-03-4

In 2010,Kino, Tatsuhito; Nagase, Yu; Ohtsuka, Yuhki; Yamamoto, Kyoko; Uraguchi, Daisuke; Tokuhisa, Kenji; Yamakawa, Tetsu published 《Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethyl sulfoxide》.Journal of Fluorine Chemistry published the findings.Reference of 3-(Trifluoromethyl)-1H-pyrazole The information in the text is summarized as follows:

The trifluoromethylation of aromatic and heteroaromatic compounds by CF3I in the presence of FeSO4, H2O2 and DMSO was investigated. Various trifluoromethylated benzenes, 6-membered N-containing arenes and 5-membered heteroarenes were obtained under mild conditions. General orientation of electrophilic aromatic substitution was observed similarly as previously reported in other radical trifluoromethylations. In the experiment, the researchers used 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Reference of 3-(Trifluoromethyl)-1H-pyrazole)

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

Norman, Natalie J.’s team published research in Journal of Organic Chemistry in 2022 | CAS: 20154-03-4

Norman, Natalie J.; Bao, Si Tong; Curts, Lynne; Hui, Tiffani; Zheng, Shao-Liang; Shou, Tiffany; Zeghibe, Ana; Burdick, Izzy; Fuehrer, Hannah; Huang, Adrian published an article in 2022. The article was titled 《Highly Selective N-Alkylation of Pyrazoles: Crystal Structure Evidence for Attractive Interactions》, and you may find the article in Journal of Organic Chemistry.SDS of cas: 20154-03-4 The information in the text is summarized as follows:

Inspired by crystal structures, authors designed and achieved a catalyst-free Michael reaction for the preparation of an N1-alkyl pyrazoles I (R1 = 3-CF3, 3-COOEt, 3-NO2-4-Br, etc.; R2 = CN, COOEt) in a high yield (>90%) with excellent regioselectivity (N1/N2 > 99.9:1). The scope of this protocol has been extended to accomplish the first general regioselective N1-alkylation of 1H-pyrazoles to give di-, tri-, and tetra-substituted pyrazoles in a single step. The resulting pyrazoles bear versatile functional groups such as bromo, ester, nitro, and nitrile, offering opportunities for late-stage functionalization. This efficient methodol. will have an impact on drug discovery, as several Food and Drug Administration-approved drugs are pyrazole derivatives A working hypothesis for the regioselectivity is proposed. X-ray crystal structures of the products that highlight the attractive interactions are discussed. This report provides a rare source for the further elucidation of the attractive interactions because the isomeric ratios and the crystal structures are directly related. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4SDS of cas: 20154-03-4)

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

Volgraf, Matthew’s team published research in Journal of Medicinal Chemistry in 2016 | CAS: 20154-03-4

In 2016,Volgraf, Matthew; Sellers, Benjamin D.; Jiang, Yu; Wu, Guosheng; Ly, Cuong Q.; Villemure, Elisia; Pastor, Richard M.; Yuen, Po-wai; Lu, Aijun; Luo, Xifeng; Liu, Mingcui; Zhang, Shun; Sun, Liang; Fu, Yuhong; Lupardus, Patrick J.; Wallweber, Heidi J. A.; Liederer, Bianca M.; Deshmukh, Gauri; Plise, Emile; Tay, Suzanne; Reynen, Paul; Herrington, James; Gustafson, Amy; Liu, Yichin; Dirksen, Akim; Dietz, Matthias G. A.; Liu, Yanzhou; Wang, Tzu-Ming; Hanson, Jesse E.; Hackos, David; Scearce-Levie, Kimberly; Schwarz, Jacob B. published 《Discovery of GluN2A-Selective NMDA Receptor Positive Allosteric Modulators (PAMs): Tuning Deactivation Kinetics via Structure-Based Design》.Journal of Medicinal Chemistry published the findings.Electric Literature of C4H3F3N2 The information in the text is summarized as follows:

The N-methyl-D-aspartate receptor (NMDAR) is a Na+ and Ca2+ permeable ionotropic glutamate receptor that is activated by the coagonists glycine and glutamate. NMDARs are critical to synaptic signaling and plasticity, and their dysfunction has been implicated in a number of neurol. disorders, including schizophrenia, depression, and Alzheimer’s disease. Herein we describe the discovery of potent GluN2A-selective NMDAR pos. allosteric modulators (PAMs) starting from a high-throughput screening hit. Using structure-based design, we sought to increase potency at the GluN2A subtype, while improving selectivity against related α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors (AMPARs). The structure-activity relationship of channel deactivation kinetics was studied using a combination of electrophysiol. and protein crystallog. Effective incorporation of these strategies resulted in the discovery of GNE-0723 (46), a highly potent and brain penetrant GluN2A-selective NMDAR PAM suitable for in vivo characterization. The results came from multiple reactions, including the reaction of 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Electric Literature of C4H3F3N2)

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

Toummini, Dounia’s team published research in Chemistry – A European Journal in 2014 | CAS: 20154-03-4

In 2014,Toummini, Dounia; Tlili, Anis; Berges, Julien; Ouazzani, Fouad; Taillefer, Marc published 《Copper-Catalyzed Arylation of Nitrogen Heterocycles from Anilines under Ligand-Free Conditions》.Chemistry – A European Journal published the findings.Related Products of 20154-03-4 The information in the text is summarized as follows:

The arylation of pyrazole and derivatives can be achieved by coupling arenediazonium species (formed in situ from anilines) by using a catalytic system that employs low-toxicity and inexpensive copper metal under very mild and ligand-free conditions (T=20 °C). From other nitrogen heterocycles, the presence of an additive (NBu4I) significantly improves the efficiency of the catalytic system. These results represent the first examples of C-N bond formation from arenediazonium species. In the experiment, the researchers used 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Related Products of 20154-03-4)

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

Testa, Christelle’s team published research in Advanced Synthesis & Catalysis in 2015 | CAS: 20154-03-4

In 2015,Testa, Christelle; Roger, Julien; Scheib, Stephanie; Fleurat-Lessard, Paul; Hierso, Jean-Cyrille published 《Palladium-Catalysed C-H Bond Electrophilic Fluorination of Highly Substituted Arylpyrazoles: Experimental and DFT Mechanistic Insights》.Advanced Synthesis & Catalysis published the findings.Related Products of 20154-03-4 The information in the text is summarized as follows:

A general protocol for palladium-catalyzed C-H mono- and di-fluorination of highly substituted arylpyrazoles is reported. Coupling pathways and substrate limitations are discussed in the light of complementary mechanistic exptl. and d. functional theory (DFT) studies. The mono- and di-ortho-fluorination of arylpyrazoles having substituted pyrazole groups and ortho-, meta-, or para-substituted arene moieties is achieved. Various pyrazole groups can efficiently promote the direct C-H activation/fluorination of substrates bearing valuable reactive ester, cyano, halide and nitro functions. The presence of methoxy, Me and trifluoromethyl is tolerated on the pyrazole directing groups. However, steric substituent effects have a marked influence which is evidenced by calculations DFT modeling suggested also a previously unseen outer-sphere oxidative addition of N-fluorobenzenesulfonimide (NFSI) to Pd(II) as an alternative mechanism to the commonly assumed Pd(II)/Pd(IV) process. This unprecedented proposal, which is supported by the mass spectrometry identification of a key Pd(II) monomer under the stoichiometric conditions deserves more attention. The influence of elaborate highly substituted directing groups on the course of Pd-catalyzed fluorination has generally received limited attention although this question has a crucial synthetic utility; herein, appropriate conditions for isolating pure products are reported. In addition to this study using 3-(Trifluoromethyl)-1H-pyrazole, there are many other studies that have used 3-(Trifluoromethyl)-1H-pyrazole(cas: 20154-03-4Related Products of 20154-03-4) was used in this study.

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

Kabir, M. Shahjahan’s team published research in Journal of Organic Chemistry in 2012 | CAS: 20154-03-4

In 2012,Kabir, M. Shahjahan; Namjoshi, Ojas A.; Verma, Ranjit; Lorenz, Michael; Phani Babu Tiruveedhula, V. V. N.; Monte, Aaron; Bertz, Steven H.; Schwabacher, Alan W.; Cook, James M. published 《Base-mediated stereospecific synthesis of aryloxy and amino substituted ethyl acrylates》.Journal of Organic Chemistry published the findings.Synthetic Route of C4H3F3N2 The information in the text is summarized as follows:

The stereospecific synthesis of aryloxy and amino substituted E- and Z-ethyl-3-acrylates is of interest because of their potential in the polymer industry and in medicinal chem. During work on a copper-catalyzed cross-coupling reaction of Et (E)- and (Z)-3-iodoacrylates with phenols and N-heterocycles, we discovered a very simple (nonmetallic) method for the stereospecific synthesis of aryloxy and amino substituted acrylates. To study this long-standing problem on the stereoselectivity of aryloxy and amino substituted acrylates, a series of O- and N-substituted nucleophiles was allowed to react with Et (E)- and (Z)-3-iodoacrylates. Screening of different bases indicated that DABCO (1,4-diazabicyclo[2.2.2]octane) afforded successful conversion of Et (E)- and (Z)-3-iodoacrylates into aryloxy and amino substituted Et acrylates in a stereospecific manner. Herein are the details of this DABCO-mediated stereospecific synthesis of aryloxy and amino substituted E- or Z-acrylates. 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)

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