pyrazoles-derivatives

Chemoselective Reduction of α-Cyano Carbonyl Compounds: Application to the Preparation of Heterocycles was written by Pollack, Scott R.;Kuethe, Jeffrey T.. And the article was included in Organic Letters in 2016.Quality Control of 3-(4-Bromophenyl)-1H-pyrazole This article mentions the following:

β-Aminoacrylates are reactive intermediates that are useful building blocks in synthesis. General methods for their preparation typically afford α and β disubstitution patterns or β only. Mols. with only α-substituents (β-hydrogen) are much less well-known. A chemoselective reductive tautomerization of α-cyanoacetates, using DIBAL-H, has been developed to access these valuable synthons. α,β-Unsaturated cyanoacetates and α-cyanoketones can, also, be selectively reduced via this methodol. A series of heterocycles were prepared using these β-enamino carbonyl compounds In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Quality Control of 3-(4-Bromophenyl)-1H-pyrazole).

3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9) 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 3-(4-Bromophenyl)-1H-pyrazole

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

Ester and Amide Derivatives of the Nonsteroidal Antiinflammatory Drug, Indomethacin, as Selective Cyclooxygenase-2 Inhibitors was written by Kalgutkar, Amit S.;Marnett, Alan B.;Crews, Brenda C.;Remmel, Rory P.;Marnett, Lawrence J.. And the article was included in Journal of Medicinal Chemistry in 2000.Computed Properties of C5H9N3 This article mentions the following:

Recent studies from our laboratory have shown that derivatization of the carboxylate moiety in substrate analog inhibitors, such as 5,8,11,14-eicosatetraynoic acid, and in nonsteroidal antiinflammatory drugs (NSAIDs), such as indomethacin and meclofenamic acid, results in the generation of potent and selective cyclooxygenase-2 (COX-2) inhibitors (Kalgutkar et al. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 925-930). This paper summarizes details of the structure-activity studies involved in the transformation of the arylacetic acid NSAID, indomethacin, into a COX-2-selective inhibitor. Many of the structurally diverse indomethacin esters and amides inhibited purified human COX-2 with IC₅₀ values in the low-nanomolar range but did not inhibit ovine COX-1 activity at concentrations as high as 66 μM. Primary and secondary amide analogs of indomethacin were more potent as COX-2 inhibitors than the corresponding tertiary amides. Replacement of the 4-chlorobenzoyl group in indomethacin esters or amides with the 4-bromobenzyl functionality or hydrogen afforded inactive compounds Likewise, exchanging the 2-Me group on the indole ring in the ester and amide series with a hydrogen also generated inactive compounds Inhibition kinetics revealed that indomethacin amides behave as slow, tight-binding inhibitors of COX-2 and that selectivity is a function of the time-dependent step. Conversion of indomethacin into ester and amide derivatives provides a facile strategy for generating highly selective COX-2 inhibitors and eliminating the gastrointestinal side effects of the parent compound In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Computed Properties of C5H9N3).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) 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.Computed Properties of C5H9N3

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

Variable-Field Study of ¹³C,^35,37Cl Residual Dipolar Coupling in the ¹³C CPMAS NMR Spectra of Pyrazole Derivatives was written by Olivieri, Alejandro C.;Elguero, Jose;Sobrados, Isabel;Cabildo, Pilar;Claramunt, Rosa M.. And the article was included in Journal of Physical Chemistry in 1994.Recommanded Product: 15953-73-8 This article mentions the following:

High-resolution solid-state ¹³C NMR spectra of the chlorinated derivatives 3,5-dimethyl-4-chloropyrazole, 4-chloro-5-methylpyrazole, and 3,5-bis(4′-chloropyrazol-1-yl)-4-chloropyrazole [I (R = Me, H) and II, resp.] were recorded at 100.6 MHz (B₀ = 9.4 T) and at 50.3 MHz (B₀ = 4.7 T). The signals of the carbons bonded to chlorine appear as doublets at 9.4 T and as broad triplets at 4.7 T, due to incompletely averaged ¹³C,^35,37Cl dipolar coupling. The line shapes can be successfully simulated assuming typical values for the C-Cl bond distance and ³⁵Cl quadrupole coupling constant (including its sign). In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8Recommanded Product: 15953-73-8).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) 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. 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. Recommanded Product: 15953-73-8

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

Discovery of a Highly Selective, Brain-Penetrant Aminopyrazole LRRK2 Inhibitor was written by Chan, Bryan K.;Estrada, Anthony A.;Chen, Huifen;Atherall, John;Baker-Glenn, Charles;Beresford, Alan;Burdick, Daniel J.;Chambers, Mark;Dominguez, Sara L.;Drummond, Jason;Gill, Andrew;Kleinheinz, Tracy;Le Pichon, Claire E.;Medhurst, Andrew D.;Liu, Xingrong;Moffat, John G.;Nash, Kevin;Scearce-Levie, Kimberly;Sheng, Zejuan;Shore, Daniel G.;Van de Poel, Herve;Zhang, Shuo;Zhu, Haitao;Sweeney, Zachary K.. And the article was included in ACS Medicinal Chemistry Letters in 2013.SDS of cas: 5334-39-4 This article mentions the following:

The modulation of LRRK2 kinase activity by a selective small mol. inhibitor has been proposed as a potentially viable treatment for Parkinson’s disease. By using aminopyrazoles as aniline bioisosteres, we discovered a novel series of LRRK2 inhibitors. Herein, we describe our optimization effort that resulted in the identification of a highly potent, brain-penetrant aminopyrazole LRRK2 inhibitor (18, I) that addressed the liabilities (e.g., poor solubility and metabolic soft spots) of our previously disclosed anilino-aminopyrimidine inhibitors. In in vivo rodent PKPD studies, 18 demonstrated good brain exposure and engendered significant reduction in brain pLRRK2 levels post-i.p. administration. The strategies of bioisosteric substitution of aminopyrazoles for anilines and attenuation of CYP1A2 inhibition described herein have potential applications to other drug discovery programs. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4SDS of cas: 5334-39-4).

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. 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: 5334-39-4

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

Electrocatalytic N-N cross-coupling of N-alkyl-3-aminopyrazoles at a nickel anode was written by Lyalin, B. V.;Sigacheva, V. L.;Petrosyan, V. A.. And the article was included in Russian Chemical Bulletin in 2020.Synthetic Route of C5H9N3 This article mentions the following:

Electrocatalytic N-N cross-coupling of N-alkyl-3-aminopyrazoles I (R¹ = Me, Et; R² = H, Me; R³ = Me, Et; R⁴ = H, Me) was made at a nickel anode. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-3-amine (cas: 55361-49-4Synthetic Route of C5H9N3).

1-Ethyl-1H-pyrazol-3-amine (cas: 55361-49-4) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. 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.Synthetic Route of C5H9N3

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

Synthesis and reactivity of enamines in pyridine series was written by Benckova, M.;Vegh, D.;Kovac, J.;Friedl, Z.. And the article was included in Chemical Papers in 1989.Safety of 3-(1H-Pyrazol-3-yl)pyridine This article mentions the following:

The preparation of (E)-RCH:CHNMe₂ (R = substituted pyridyl) by the reaction of suitably substituted picolines, lutidines, and collidines with Me₂NCH(OMe)₂ was described. By the same method enamino ketones derived from acetylpyridines were prepared The rotational barriers of these enamino ketones were measured by dynamic NMR spectroscopy. The enamino ketones were cyclized with N₂H₄ and NCCH₂CONMe₂. E.g., (E)-R¹COCH:CHNMe₂ (R¹ = 2-pyridyl) gives pyrazole I and pyridinone II, resp. In the experiment, the researchers used many compounds, for example, 3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9Safety of 3-(1H-Pyrazol-3-yl)pyridine).

3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9) 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. 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.Safety of 3-(1H-Pyrazol-3-yl)pyridine

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

Discovery of Potent and Broad-Spectrum Pyrazolopyridine-Containing Antivirals against Enteroviruses D68, A71, and Coxsackievirus B3 by Targeting the Viral 2C Protein was written by Hu, Yanmei;Kitamura, Naoya;Musharrafieh, Rami;Wang, Jun. And the article was included in Journal of Medicinal Chemistry in 2021.Safety of 1-Ethyl-1H-pyrazol-5-amine This article mentions the following:

The enterovirus genus of the picornavirus family contains many important human pathogens. EV-D68 primarily infects children, and the disease manifestations range from respiratory illnesses to neurol. complications such as acute flaccid myelitis (AFM). EV-A71 is a major pathogen for the hand, foot, and mouth disease (HFMD) in children and can also lead to AFM and death in severe cases. CVB3 infection can cause cardiac arrhythmias, acute heart failure, as well as type 1 diabetes. There is currently no FDA-approved antiviral for any of these enteroviruses. In this study, we report our discovery and development of pyrazolopyridine-containing small mols. such as I with potent and broad-spectrum antiviral activity against multiple strains of EV-D68, EV-A71, and CVB3. Serial viral passage experiments, coupled with reverse genetics and thermal shift binding assays, suggested that these mols. target the viral protein 2C. Overall, the pyrazolopyridine inhibitors represent a promising class of candidates for the urgently needed nonpolio enterovirus antivirals. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Safety of 1-Ethyl-1H-pyrazol-5-amine).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. 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.Safety of 1-Ethyl-1H-pyrazol-5-amine

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

Antiparasitic Lead Discovery: Toward Optimization of a Chemotype with Activity Against Multiple Protozoan Parasites was written by Devine, William;Thomas, Sarah M.;Erath, Jessey;Bachovchin, Kelly A.;Lee, Patricia J.;Leed, Susan E.;Rodriguez, Ana;Sciotti, Richard J.;Mensa-Wilmot, Kojo;Pollastri, Michael P.. And the article was included in ACS Medicinal Chemistry Letters in 2017.SDS of cas: 3528-58-3 This article mentions the following:

Human African trypanosomiasis (HAT), Chagas disease, and leishmaniasis present a significant burden across the developing world. Existing therapeutics for these protozoal neglected tropical diseases suffer from severe side effects and toxicity. Previously, NEU-1045 was identified as a promising lead with cross-pathogen activity, though it possessed poor physicochem. properties. The authors have designed a library of analogs with improved calculated physicochem. properties built on the quinoline scaffold of 3 incorporating small, polar aminoheterocycles in place of the 4-(3-fluorobenzyloxy)aniline substituent. The authors report the biol. activity of these inhibitors against Trypanosoma brucei (HAT), T. cruzi (Chagas disease), and Leishmania major (cutaneous leishmaniasis), and describe the identification of N-(5-chloropyrimidin-2-yl)-6-(4-(morpholinosulfonyl)phenyl)quinolin-4-amine (13t) as a promising inhibitor of L. major proliferation and 6-(4-(morpholinosulfonyl)phenyl)-N-(pyrimidin-4-yl)quinolin-4-amine (13j), a potent inhibitor of T. brucei proliferation with improved drug-like properties. 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. 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. 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.SDS of cas: 3528-58-3

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

Photoluminescence and electroluminescence of four orange-red and red organic iridium(III) complexes was written by Su, Ning;Zheng, You-Xuan. And the article was included in Journal of Organometallic Chemistry in 2018.SDS of cas: 19959-77-4 This article mentions the following:

Using 1-(4-(trifluoromethyl)phenyl)isoquinoline (tfmpiq) and 4-(4-(trifluoromethyl)phenyl) quinazoline (tfmpqz) as the main ligands and pyrazole pyridine derivatives (mepzpy: 2-(3-methyl-1H-pyrazol-5-yl)pyridine, cf3pzpy: 2-(3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridine) as the ancillary ligands, four iridium(III) complexes (PIQ-Ir1-me, PIQ-Ir2-cf3, PQZ-Ir3-me and PQZ-Ir4-cf3) were synthesized and investigated. Due to the variation of the ligands, these Ir(III) complexes showed different emissions peaking from 602 to 628 nm with the phosphorescence quantum yields of 0.40-0.67. Moreover, applying these Ir(III) complexes as emitters, the organic light-emitting diodes (OLEDs) with the configuration of ITO/HATCN (hexaazatriphenylenehexacabonitrile, 5 nm)/TAPC (bis[4-(N,N-ditolylamino)-phenyl] cyclohexane, 50 nm)/Ir(III) complexes (8 wt%): TCTA (4,4′,4”-tri(9-carbazoyl)triphenylamine, 20 nm)/TmPyPB (1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 40 nm)/LiF (1 nm)/Al (100 nm) exhibited good performances. Especially, the device with orange-red PQZ-Ir4-cf3 emitter obtained the best device performances with the maximum current efficiency of 40.04 cd A^-1 and the maximum power efficiency of 33.98 lm W^-1. For the pure red complex PQZ-Ir4-me with CIE coordinates at (0.64, 0.34) showed the maximum external quantum efficiency of 22.3%. In the experiment, the researchers used many compounds, for example, 2-(5-Methyl-1H-pyrazol-3-yl)pyridine (cas: 19959-77-4SDS of cas: 19959-77-4).

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

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

Synthesis of pyrazole (hemi)aminals via the cleavage of saturated aliphatic ether C-O bonds in the presence of ferric halides was written by Govor, Evgen V.;Sanakis, Yiannis;Raptis, Raphael G.. And the article was included in New Journal of Chemistry in 2017.Recommanded Product: 4-Chloro-3,5-dimethyl-1H-pyrazole This article mentions the following:

The discovery of reactions using previously considered inert functional groups opens up new paths towards the synthesis of desired products. Solutions of mononuclear ferric-pyrazole complexes react with di-Et ether cleaving a C-O bond to form chelating hemiaminals. Upon exposure to diffuse light, the latter react further to yield mononuclear ferrous products containing chelating aminals. 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. 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. 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.Recommanded Product: 4-Chloro-3,5-dimethyl-1H-pyrazole

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