Tag: 100-200

New reaction of 1H-pyrazoles with selenium dioxide: one-pot synthesis of bis(1H-pyrazol-4-yl)selenides was written by Seredyuk, Maksym;Fritsky, Igor O.;Kraemer, Roland;Kozlowski, Henryk;Haukka, Matti;Guetlich, Philipp. And the article was included in Tetrahedron in 2010.Recommanded Product: 2-(5-Methyl-1H-pyrazol-3-yl)pyridine This article mentions the following:

A novel reaction between six 3- and 3,5-substituted pyrazoles with Se dioxide proceeds with formation of bis(3R,5R’-1H-pyrazol-4-yl)selenides (R = pyridyl, Ph, Et, Me, H; R’ = Me, Et, H) in 52% to 67% yield. On this basis, an efficient 1-pot synthetic procedure was developed. E.g., reaction of 3-methyl-5-phenyl-1H-pyrazole, SeO₂ and pyridine afforded bis(3-methyl-5-phenyl-1H-pyrazol-4-yl) selenide in 67% yield. In the case of the unsubstituted pyrazole a selenonium compound was obtained. The identity and structure of the seven isolated Se derivatives were confirmed by spectral methods and their mol. structures studied by x-ray anal. 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 and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. 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

Reaction of ethyl-4,4,4-trifluoroacetoacetate with cyanoacetic acid hydrazide. Novel rearrangement of 1-aminopyridine derivatives was written by Balicki, Roman;Nantka-Namirski, Pawel. And the article was included in Acta Poloniae Pharmaceutica in 1975.Category: pyrazoles-derivatives This article mentions the following:

CF3COCH2CO2Et (I) condensed with NCCH2CONHNH2 (II) in EtOH in the presence of piperidine (III) yielded 15% IV and an unidentified by-product. The same reaction effected in III without any solvent gave, upon acidification, 70% V. I and II condensed in EtOH with KOH as the catalyst yielded the K salt of VI, which on acidification rearranged to V. Similarly, only V was obtained in the reaction of I with 5-aminopyrazol-3-one. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0Category: pyrazoles-derivatives).

3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0) 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.Category: pyrazoles-derivatives

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

Design, synthesis, and structure-activity relationships of 1-ethylpyrazole-3-carboxamide compounds as novel hypoxia-inducible factor (HIF)-1 inhibitors was written by Yasuda, Yorinobu;Arakawa, Takeaki;Nawata, Yumi;Shimada, Sayaka;Oishi, Shinya;Fujii, Nobutaka;Nishimura, Shinichi;Hattori, Akira;Kakeya, Hideaki. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Category: pyrazoles-derivatives This article mentions the following:

Hypoxia-inducible factor (HIF)-1 is well known as a promising target for cancer chemotherapy. By screening an inhouse chem. library using a hypoxia-responsive luciferase reporter gene assay, the authors identified CLB-016 containing 1-ethylpyrazole-3-carboxamide as a HIF-1 inhibitor (IC₅₀ = 19.1 μM). In a subsequent extensive structure-activity relationship (SAR) study, the authors developed compound 11Ae (4-[5-[(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)methyl]furan-2-carboxamido]-1-ethyl-1H-pyrazole-3-carboxamide) with an IC₅₀ value of 8.1 μM against HIF-1-driven luciferase activity. CLB-016 and compound 11Ae were shown to significantly suppress the HIF-1-mediated hypoxia response, including carbonic anhydrase IX (CAIX) gene expression and migration of human sarcoma HT1080 cells. These results revealed 1-ethylpyrazole-3-carboxamide as a novel scaffold to develop promising anti-cancer drugs targeting the HIF-1 signaling pathway. 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. 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.Category: pyrazoles-derivatives

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

Determination of volatile component from Patrinia villosa (Thunb.) Juss. and Patrinia scabiosaefolia Fisch by GC- MS was written by Liu, Wei;Jia, Shao-hua;Xiang, Zheng. And the article was included in Harbin Shangye Daxue Xuebao, Ziran Kexueban in 2016.Quality Control of 1-Ethyl-1H-pyrazol-5-amine This article mentions the following:

To analyze the chem. constituents in the essential oil of Patrinia villosa (Thunb.) Juss and Patrinia scabiosaefolia Fisch. The essential oil obtained by the hydrodistillation of the leaves of Patrinia scabiosaefolia Fisch and Patrinia villosa( Thunb.) Juss. were analyzed by a combination of capillary GC/MS analytic techniques. Results indicated that 54 components comprising 94.56% of essential oil in leaves of P. scabiosaefolia Fisch and 36 components comprising 89.87% of oil in leaves of P. Villosa Juss. were identified, resp. 9 Common constituents, hexanal, 2-Pentylfuran, benzeneacetaldehyde, α-Ionene, 1, 2, 3, 4- Tetrahydro-1, 6, 8-trimthylnaphthalene, 1, 2, 3, 4-Tetrahydro-1, 5, 7-trimethylnaphthalene, β-Damascenone, Hexahydrofarnesylacetone and palmitic acid, were identified in two species of Baijiangcao. This was the first report to make a comparison of essential oil constituents in two species of BaiJiangCao, which could have identification between the two leaves on essential oil ingredient, and even could give a support for quality control. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Quality Control of 1-Ethyl-1H-pyrazol-5-amine).

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

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

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

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

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