Category: pyrazoles-derivatives

Li, Chengxi published the artcileChemo- and regioselective defluorinative annulation of (trifluoromethyl)alkenes with pyrazolones: synthesis and insecticidal activity of 6-fluoro-1,4-dihydropyrano[2,3-c]pyrazoles, Formula: C10H9ClN2O, the publication is Organic Chemistry Frontiers (2022), 9(17), 4692-4698, database is CAplus.

The chemo- and regioselective defluorinative [3 + 3] annulation of (trifluoromethyl)alkenes and pyrazolones was reported that gives rise to various useful 6-fluoro-1,4-dihydropyrano[2,3-c]pyrazoles I [R = Ph, 4-MeC₆H₄, 4-ClC₆H₄, etc.; R¹ = Ph, 3-MeC₆H₄, 4-ClC₆H₄, etc.; R² = Me, Et, Bn, etc.] in high yields. This reaction distinguished the different nucleophilic sites of pyrazolones and featured mild conditions, a broad substrate scope, and gram-scalability. A simple derivation of the obtained 6-fluoro-1,4-dihydropyrano[2,3-c]pyrazoles efficiently afforded diverse useful compounds Significantly, compound I [R = 4-F₃CC₆H₄, R¹ = 2-ClC₆H₄, R² = Me] exhibited up to 100% insecticidal activity against Plutella xylostella, which was a destructive pest worldwide. Mechanism studies indicated that this reaction proceeded via a chemo- and regioselective S_N2’/S_NV pathway and that the double defluorinative alkylation of pyrazolones with (trifluoromethyl)alkenes was completely inhibited.

Organic Chemistry Frontiers published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, Formula: C10H9ClN2O.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Wu, Yuchuan published the artcileDiscovery of potent and selective matrix metalloprotease 12 inhibitors for the potential treatment of chronic obstructive pulmonary disease (COPD), Product Details of C3H5BN2O2, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(1), 138-143, database is CAplus and MEDLINE.

Chronic obstructive pulmonary disease (COPD) is an inflammatory lung disease associated with irreversible progressive airflow limitation. Matrix metalloproteinase-12 (MMP-12) has been characterized to be one of the major proteolytic enzymes to induce airway remodeling, destruction of elastin and the aberrant remodeling of damaged alveoli in COPD and asthma. The goal of this project is to develop and identify an orally potent and selective small mol. inhibitor of MMP-12 for treatment of COPD and asthma. Syntheses and structure-activity relationship (SAR) studies of a series of dibenzofuran (DBF) sulfonamides as MMP-12 inhibitors are described. Potent inhibitors of MMP-12 with excellent selectivity against other MMPs were identified. Compound I (MMP118), which exhibits excellent oral efficacy in the MMP-12 induced ear-swelling inflammation and lung inflammation mouse models, had been successfully advanced into Development Track status.

Bioorganic & Medicinal Chemistry Letters published new progress about 724710-02-5. 724710-02-5 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Pyrazole,Boronic Acids,Boronic acid and ester, name is (1H-Pyrazol-5-yl)boronic acid, and the molecular formula is C24H12, Product Details of C3H5BN2O2.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Xu, Li-Ying published the artcile(4Z)-4-[(2-Chloroanilino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, Synthetic Route of 4551-69-3, the publication is Acta Crystallographica, Section E: Structure Reports Online (2012), 68(6), o1843, database is CAplus and MEDLINE.

The title compound, C₂₃H₁₈ClN₃O, exists in an enamine-keto form with the amino group involved in an intramol. N-H···O hydrogen bond. The five-membered ring is nearly planar, the largest deviation being 0.0004 (7) Å, and makes dihedral angles of 16.62 (6), 41.89 (5) and 71.27 (4)° with the Ph rings. In the crystal, weak C-H···O hydrogen bonds link the mols. into supramol. chains along the b axis. Crystallog. data are given.

Acta Crystallographica, Section E: Structure Reports Online published new progress about 4551-69-3. 4551-69-3 belongs to pyrazoles-derivatives, auxiliary class Benzenes, name is 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and the molecular formula is C17H20ClN3, Synthetic Route of 4551-69-3.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Wu, Xiren published the artcileSynthesis, characterization and antibacterial activity of taurine PMBP schiff base and their metal complexes, Recommanded Product: 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, the publication is Guangdong Weiliang Yuansu Kexue (2013), 20(4), 18-22, database is CAplus.

Objective: Synthesis of novel taurine schiff base and its metal complexes, and study on the antibacterial activities. Method: The schiff base is dissolved in absolute Me alc., and mixed with four kinds of Zn(II), Co(II), Ni(II), Cu(II) metal acetate sep. After heating under reflux, filtration and drying, we get the target compounds The element anal., IR spectra and molar conductance were used to analyze the structure and composition of the schiff base and its Zn(II), Co(II), Ni(II), Cu(II) complexes. The drilling method is used to examine the complexes antibacterial activities. Result: Four kinds of complexes M(L)(H₂O)_2∼3 belong to 1:1 non-electrolyte. The primary biol. activity assay showed that all products exhibited medium to high antibacterial activities against E. coli and Streptococcus pneumoniae, among which the Cu(II) and Co(II) complexes of the schiff base gave the strongest activity which is better than that of the schiff base. Conclusion: The preparation of the taurine-PMBP metal complex provides new content for the coordination chem. Good antibacterial activity provides the basis for its application in medicine.

Guangdong Weiliang Yuansu Kexue published new progress about 4551-69-3. 4551-69-3 belongs to pyrazoles-derivatives, auxiliary class Benzenes, name is 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and the molecular formula is C6H8O4, Recommanded Product: 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Jagtap, Ajit Dhananjay published the artcile4-Substituted 2-amino-3,4-dihydroquinazolines with a 3-hairpin turn side chain as novel inhibitors of BACE-1, Recommanded Product: 1-Methylpyrazole, the publication is Bioorganic Chemistry (2020), 103135, database is CAplus and MEDLINE.

Herein, the authors report the identification, design, and synthesis of a series of 4-substituted 2-amino-3,4-dihydroquinazolines I [R¹ = Me, CH:CH₂, Bn, etc., R² = Me, cyclopropyl, (1-methyl-1H-pyrazol-4-yl)methyl] with hairpin turn side chains as novel inhibitors of BACE-1. The dihydroquinazoline derivatives were rationally designed by modifying the amide group and relocating the α-hydrophobic substituent on the hairpin turn side chain of lead compound II to the C4-position on the 3,4-dihydroquinazoline scaffold to facilitate interactions with the S₁, S₂ and S₁‘ subsites of BACE-1. Among these derivatives, two compounds exhibited potent BACE-1 inhibitory activity: 4-methyl-substituted derivative I [R¹ = Me, R² = (1-methyl-1H-pyrazol-4-yl)methyl] (BACE-1 CFA IC₅₀ = 0.38μM; BACE-1 WCA IC₅₀ = 0.14μM) and 4-cyclohexylmethyl-substituted derivative I [R¹ = cyclohexylmethyl, R² = (1-methyl-1H-pyrazol-4-yl)methyl] (BACE-1 CFA IC₅₀ = 0.49μM; BACE-1 WCA IC₅₀ = 0.14μM). The results suggest that the structural modifications maintain the hairpin turn topol. similar to that of compound II and provide an addnl. interaction with the S₂ subsite.

Bioorganic Chemistry published new progress about 930-36-9. 930-36-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole, name is 1-Methylpyrazole, and the molecular formula is C4H6N2, Recommanded Product: 1-Methylpyrazole.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Thottacherry, Joseph Jose published the artcileMechanochemical feedback control of dynamin independent endocytosis modulates membrane tension in adherent cells, HPLC of Formula: 71203-35-5, the publication is Nature Communications (2018), 9(1), 1-14, database is CAplus and MEDLINE.

Plasma membrane tension regulates many key cellular processes. It is modulated by, and can modulate, membrane trafficking. However, the cellular pathway(s) involved in this interplay is poorly understood. Here we find that, among a number of endocytic processes operating simultaneously at the cell surface, a dynamin independent pathway, the CLIC/GEEC (CG) pathway, is rapidly and specifically upregulated upon a sudden reduction of tension. Moreover, inhibition (activation) of the CG pathway results in lower (higher) membrane tension. However, alteration in membrane tension does not directly modulate CG endocytosis. This requires vinculin, a mechano-transducer recruited to focal adhesion in adherent cells. Vinculin acts by controlling the levels of a key regulator of the CG pathway, GBF1, at the plasma membrane. Thus, the CG pathway directly regulates membrane tension and is in turn controlled via a mechano-chem. feedback inhibition, potentially leading to homeostatic regulation of membrane tension in adherent cells.

Nature Communications published new progress about 71203-35-5. 71203-35-5 belongs to pyrazoles-derivatives, auxiliary class GPCR/G Protein,Ras, name is 4-(5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide, and the molecular formula is C20H19NO4, HPLC of Formula: 71203-35-5.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Kasparkova, Jana published the artcileNovel cis-Pt(II) complexes with alkylpyrazole ligands: synthesis, characterization, and unusual mode of anticancer action, Quality Control of 930-36-9, the publication is Bioinorganic Chemistry and Applications (2022), 1717200, database is CAplus and MEDLINE.

One concept of improving anticancer effects of conventional platinum-based antitumor drugs consists of conjugating these compounds with other biol. (antitumor) active agents, acting by a different mechanism. Here, we present synthesis, physicochem. characterization, biol. effects, and mechanisms of action of four new analogs of conventional cisplatin, namely, cis-Pt(II) complexes containing either Me or Et pyrazole N-donor ligands and chlorido or iodido ligands. It is noteworthy that while chlorido complexes display activity in a variety of cancer cell lines comparable to cisplatin, iodido complexes are considerably more potent due to their enhanced hydrophobicity and consequently enhanced cellular accumulation. Moreover, all of the studied Pt(II) alkylpyrazole complexes display a higher selectivity for tumor cells and effectively overcome the acquired resistance to cisplatin. Further results focused on the mechanism of action of the studied complexes and showed that in contrast to cisplatin and several platinum-based antitumor drugs, DNA damage by the investigated Pt(II)-alkylpyrazole complexes does not play a major role in their mechanism of action. Our findings demonstrate that inhibition of the tubulin kinesin Eg5, which is essential for forming a functional mitotic spindle, plays an important role in their mechanism of antiproliferative action.

Bioinorganic Chemistry and Applications published new progress about 930-36-9. 930-36-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole, name is 1-Methylpyrazole, and the molecular formula is C4H6N2, Quality Control of 930-36-9.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Ul′yanovskii, Nikolay V. published the artcileRapid quantification and screening of nitrogen-containing rocket fuel transformation products by vortex assisted liquid-liquid microextraction and gas chromatography – high-resolution Orbitrap mass spectrometry, Formula: C4H6N2, the publication is Microchemical Journal (2021), 106821, database is CAplus.

Existing and newly developed technologies for clean-up of wastewaters and soils contaminated with rocket fuel unsym. dimethylhydrazine (UDMH) are based on the oxidative treatment, as well as gasification in supercritical water. Being easily transformed by a radical mechanism, UDMH is capable of producing an extremely wide range of potentially hazardous nitrogen-containing products. Their identification and simultaneous quantification at low concentrations in water samples by gas chromatog. is a challenging task requiring a matrix change. We proposed a combination of dispersive vortex-assisted liquid-liquid microextraction (VALLME) of analytes followed by gas chromatog. – Orbitrap mass spectrometry allowing simultaneous target anal. and non-targeted screening. Dichloromethane and chloroform provided rapid (10 min) and effective extraction of most of UDMH transformation products. The maximum recoveries were achieved by alkalizing and saturating the aqueous samples with ammonium sulfate. The use of pyridine-d5 as an internal standard allowed developing an approach to the simultaneous determination of 24 compounds of various classes with detection limits for the most analytes in the range 0.02-1.1 μg L^-1 and accuracy of 81-117% with low-cost, simple, and rapid sample preparation procedure. Extraction with a 100 μL of chloroform allowed further increasing sensitivity up to one order of magnitude and attaining LOD values for 20 compounds in the range of 0.002-0.1 μg L^-1 comparable with that obtained by vacuum-assisted headspace solid-phase microextraction The developed method was validated and tested for the analyses of real samples – degraded aqueous solution of rocket fuel, products of UDMH treatment in supercritical water and aqueous extract of soil from the place of carrier rocket accidental crash. Twenty-nine compounds that were not previously described as UDMH transformation products were tentatively identified.

Microchemical Journal published new progress about 930-36-9. 930-36-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole, name is 1-Methylpyrazole, and the molecular formula is C10H14O, Formula: C4H6N2.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Ivachtchenko, Alexandre V. published the artcileSynthesis of pinacol esters of 1-alkyl-1H-pyrazol-5-yl- and 1-alkyl-1H-pyrazol-4-ylboronic acids, Quality Control of 847818-64-8, the publication is Journal of Heterocyclic Chemistry (2004), 41(6), 931-939, database is CAplus.

1-Substituted pyrazolylboronic acids and their pinacol esters were prepared by lithiation-borylation reaction sequence starting from bromopyrazoles. Alkylation of 4-bromo-1H-pyrazole gave 1-alkyl-4-bromo-1H-pyrazoles, which were lithiated at -80° and borylated with B(OMe)₃ to give 1-R-1H-pyrazole-4-boronic acids [4a–g, R = Me, Et, Pr, (CH₂)₂CHMe₂, (CH₂)₂OMe, (CH₂)₃NMe₂, (CH₂)₂CH(OEt)₂]. Lithiation of 4-bromo-1-(2-dimethylaminoethyl)-1H-pyrazole (2h) gave 5-lithio-derivative, which on borylation afforded 1-R¹-4-Br-1H-pyrazole-5-boronic acid (8). Boronic acids 4a–g are unstable and were deborylated slowly due to hydrolysis by traces of water; the stability of boryl derivatives can be greatly enhanced by converting to corresponding pinacol boronates (10a–g). Direct lithiation of 1-R²-1H-pyrazoles by BuLi at -20° afforded 5-lithio-derivatives, which were converted to corresponding 1-R²-1H-pyrazole-5-boronic acids [17a–e; R² = Me, ⁱBu, Pr, (CH₂)₂CHMe₂, (CH₂)₂CH(OEt)₂] and their pinacol boronates (18a–e, same R²). The key step in the described methodol. is the regioselective lithiation of the pyrazole ring. The synthesized pinacolates are stable under prolonged storage and can be used as convenient reagents in organic synthesis.

Journal of Heterocyclic Chemistry published new progress about 847818-64-8. 847818-64-8 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Pyrazole,Boronic Acids,Boronic acid and ester, name is (1-Isobutyl-1H-pyrazol-5-yl)boronic acid, and the molecular formula is C7H13BN2O2, Quality Control of 847818-64-8.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Ivachtchenko, Alexandre V. published the artcileSynthesis of pinacol esters of 1-alkyl-1H-pyrazol-5-yl- and 1-alkyl-1H-pyrazol-4-ylboronic acids, SDS of cas: 847818-66-0, the publication is Journal of Heterocyclic Chemistry (2004), 41(6), 931-939, database is CAplus.

1-Substituted pyrazolylboronic acids and their pinacol esters were prepared by lithiation-borylation reaction sequence starting from bromopyrazoles. Alkylation of 4-bromo-1H-pyrazole gave 1-alkyl-4-bromo-1H-pyrazoles, which were lithiated at -80° and borylated with B(OMe)₃ to give 1-R-1H-pyrazole-4-boronic acids [4a–g, R = Me, Et, Pr, (CH₂)₂CHMe₂, (CH₂)₂OMe, (CH₂)₃NMe₂, (CH₂)₂CH(OEt)₂]. Lithiation of 4-bromo-1-(2-dimethylaminoethyl)-1H-pyrazole (2h) gave 5-lithio-derivative, which on borylation afforded 1-R¹-4-Br-1H-pyrazole-5-boronic acid (8). Boronic acids 4a–g are unstable and were deborylated slowly due to hydrolysis by traces of water; the stability of boryl derivatives can be greatly enhanced by converting to corresponding pinacol boronates (10a–g). Direct lithiation of 1-R²-1H-pyrazoles by BuLi at -20° afforded 5-lithio-derivatives, which were converted to corresponding 1-R²-1H-pyrazole-5-boronic acids [17a–e; R² = Me, ⁱBu, Pr, (CH₂)₂CHMe₂, (CH₂)₂CH(OEt)₂] and their pinacol boronates (18a–e, same R²). The key step in the described methodol. is the regioselective lithiation of the pyrazole ring. The synthesized pinacolates are stable under prolonged storage and can be used as convenient reagents in organic synthesis.

Journal of Heterocyclic Chemistry published new progress about 847818-66-0. 847818-66-0 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Boronic Acids,Boronic Acids,Boronic acid and ester, name is (1-Isopentyl-1H-pyrazol-5-yl)boronic acid, and the molecular formula is C8H15BN2O2, SDS of cas: 847818-66-0.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics