Month: November 2022

De Pascali, Sandra A. published the artcileSynthesis, Crystal Structure, and Biological Study of Pt^II Complexes with 4-Acyl-5-pyrazolones, Product Details of C17H14N2O2, the publication is European Journal of Inorganic Chemistry (2014), 2014(7), 1249-1259, database is CAplus.

The syntheses of new Pt^II complexes with 4-acyl-5-pyrazolones [HQ^Ph = 1-phenyl-3-methyl-4-benzoylpyrazol-5-one, a; HQ^py,CF3 = 1-(2-pyridyl)-3-methyl-trifluoroacetylpyrazol-5-one, b] are reported: trans-[PtCl₂(DMSO)(HQ^Ph)] (1a), cis-[PtCl₂(DMSO)(HQ^Ph)] (2a), [PtCl(DMSO)(Q^py,CF3)] (1b), and [PtCl₂(KQ^py,CF3)] (2b). All complexes were characterized by multinuclear (¹H, ¹³C, ¹⁹F, and ¹⁹⁵Pt), multidimensional NMR spectroscopy and single-crystal x-ray diffraction analyses. The isomer trans-[PtCl₂(DMSO)(HQ^Ph)] (1a) crystallizes in two polymorphic forms, which correspond to two different conformers. In the trans-syn conformer (1a_M) (monoclinic, space group P2₁/c), the H atom of the enol group [O(1)H(1)] establishes an intramol. hydrogen bond with the ketone oxygen (O2), whereas in the trans-anti conformer (1a_O) (orthorhombic, space group Pca2₁), the same groups are involved in an analogous intermol. H bond. Interestingly, the cis isomer (2a) showed in solution and at room temperature slow rotation around both the Pt-N1 and the Pt-S bonds, which restrained both the acylpyrazolone and DMSO ligand motion. Moreover, the water solubility of the complexes trans- and cis-[PtCl₂(DMSO)(HQ^Ph)] (1a and 2a) and [PtCl₂(KQ^py,CF3)] (2b) allowed to perform in vitro biol. assays on platinum-sensitive human endometrium (HeLa) and platinum-resistant human breast (MCF-7) cancer cell lines. It was also possible to compare their cytotoxicity to cisplatin. Interestingly, trans isomer 1a showed higher cytotoxicity on HeLa cells compared to the cis isomer 2a.

European Journal of Inorganic Chemistry 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 C17H14N2O2, Product Details of C17H14N2O2.

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

Zhang, Xin-Ke published the artcileIodine-catalyzed oxidative annulation: facile synthesis of pyrazolooxepinopyrazolones via methyl azaarene sp³ C-H functionalization, Synthetic Route of 14580-22-4, the publication is Organic & Biomolecular Chemistry (2022), 20(6), 1236-1242, database is CAplus and MEDLINE.

An iodine-catalyzed Me azaarene sp³ C-H functionalization has been developed for the synthesis of a seven-membered O-heterocyclic architecture containing three different heterocyclic aromatic hydrocarbons. This method can be applied to a wide range of substituted Me azaarenes and diverse 2,4-dihydro-3H-pyrazol-3-ones, and brings about the efficient preparation of 2,9-dihydrooxepino[2,3-c:6,5-c’]dipyrazol-3(7H)-ones in high yields with the merits of low catalyst loading, good functional group tolerance and metal-free conditions.

Organic & Biomolecular Chemistry 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 C7H10BNO3, Synthetic Route of 14580-22-4.

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

Caroff, Eva published the artcileOptimization of 2-phenyl-pyrimidine-4-carboxamides towards potent, orally bioavailable and selective P2Y₁₂ antagonists for inhibition of platelet aggregation, Recommanded Product: 1H-Pyrazole-4-boronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2014), 24(17), 4323-4331, database is CAplus and MEDLINE.

2-Phenyl-4-pyrimidinecarboxamide analogs were identified as P2Y₁₂ antagonists. Optimization of the carbon-linked or nitrogen-linked substituent at the 6-position of the pyrimidine ring provided compounds with excellent ex vivo potency in the platelet aggregation assay in human plasma. One compound met the objectives for activity, selectivity and ADMET properties. The synthesis of the target compounds was achieved using (γS)-γ-[[(6-chloro-2-phenyl-4-pyrimidinyl)carbonyl]amino]-4-(ethoxycarbonyl)-δ-oxo-1-piperazinepentanoic acid 1,1-dimethylethyl ester and (γS)-4-(butoxycarbonyl)-γ-[[(6-chloro-2-phenyl-4-pyrimidinyl)carbonyl]amino]-δ-oxo-1-piperazinepentanoic acid 1,1-dimethylethyl ester as key intermediates.

Bioorganic & Medicinal Chemistry Letters published new progress about 763120-58-7. 763120-58-7 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is 1H-Pyrazole-4-boronic acid, and the molecular formula is C3H5BN2O2, Recommanded Product: 1H-Pyrazole-4-boronic acid.

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

Bachmann, Fabio published the artcileCytochrome P450 1A2 is the most important enzyme for hepatic metabolism of the metamizole metabolite 4-methylaminoantipyrine, Computed Properties of 930-36-9, the publication is British Journal of Clinical Pharmacology (2022), 88(4), 1885-1896, database is CAplus and MEDLINE.

Metamizole (dipyrone) is a prodrug not detectable in serum or urine after oral ingestion. The primary metabolite, 4-methylaminoantipyrine (4-MAA), can be N-demethylated to 4-aminoantipyrine (4-AA) or oxidized to 4-formylaminoantipyrine (4-FAA) by cytochrome P 450 (CYP)-dependent reactions. We aimed to identify the CYPs involved in 4-MAA metabolism and to quantify the effect of CYP inhibition on 4-MAA metabolism We investigated the metabolism of 4-MAA in vitro using CYP expressing supersomes and the pharmacokinetics of metamizole in the presence of CYP inhibitors in male subjects. The experiments in supersomes revealed CYP1A2 as the major CYP for 4-MAA N-demethylation and 4-FAA formation with CYP2C19 and CYP2D6 contributing to N-demethylation. In the clin. study, we investigated the influence of ciprofloxacin (CYP1A2 inhibitor), fluconazole (CYP2C19 inhibitor) and the combination ciprofloxacin/fluconazole on the pharmacokinetics of metamizole in n = 12 male subjects in a randomized, placebo-controlled, double-blind study. The geometric mean ratios for the area under the concentration-time curve of 4-MAA after/before treatment were 1.17 (90% CI 1.09-1.25) for fluconazole, 1.51 (90% CI 1.42-1.60) for ciprofloxacin and 1.92 (90% CI 1.81-2.03) for ciprofloxacin/fluconazole. Fluconazole increased the half-life of 4-MAA from 3.22 h by 0.47 h (95% CI 0.13-0.81, P < .05), ciprofloxacin by 0.69 h (95% CI 0.44-0.94, P < .001) and fluconazole/ciprofloxacin by 2.85 h (95% CI 2.48-3.22, P < .001). CYP1A2 is the major CYP for the conversion of 4-MAA to 4-AA and 4-FAA. The increase in 4-MAA exposure by the inhibition of CYP1A2 and by the combination CYP1A2/CYP2C19 may be relevant for dose-dependent adverse reactions of 4-MAA.

British Journal of Clinical Pharmacology 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, Computed Properties of 930-36-9.

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

Antolin, Albert A. published the artcileDistant Polypharmacology among MLP Chemical Probes, Quality Control of 71203-35-5, the publication is ACS Chemical Biology (2015), 10(2), 395-400, database is CAplus and MEDLINE.

Small mols. are essential tool compounds to probe the role of proteins in biol. and advance toward more efficient therapeutics. However, they are used without a complete knowledge of their selectivity across the entire proteome, at risk of confounding their effects due to unknown off-target interactions. Current state-of-the-art computational approaches to predicting the affinity profile of small mols. offer a means to anticipate potential nonobvious selectivity liabilities of chem. probes. The application of in silico target profiling on the full set of chem. probes from the NIH Mol. Libraries Program (MLP) resulted in the identification of biol. relevant in vitro affinities for proteins distantly related to the primary targets of ML006, ML123, ML141, and ML204, helping to lower the risk of their further use in chem. biol.

ACS Chemical Biology 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 C22H21N3O3S, Quality Control of 71203-35-5.

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

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, 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

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

Lakhey, Nivrutti published the artcileToxicity of azoles towards the anaerobic ammonium oxidation (anammox) process, Safety of 1-Methylpyrazole, the publication is Journal of Chemical Technology and Biotechnology (2020), 95(4), 1057-1063, database is CAplus.

Azoles are an important class of compounds that are widely used as corrosion inhibitors in aircraft de-icing agents, cooling towers, semiconductor manufacturing and household dishwashing detergents. They also are important moieties in pharmaceutical drugs and fungicides. Azoles are widespread emerging contaminants occurring frequently in water bodies. Azole compounds can potentially cause inhibition towards key biol. processes in natural ecosystems and wastewater treatment processes. Of particular concern is the inhibition of azoles to the nitrification process (aerobic oxidation of ammonium). This study investigated the acute toxicity of azole compounds towards the anaerobic ammonia oxidation (anammox) process, which is an important environmental biotechnol. gaining traction for nutrient-nitrogen removal during wastewater treatment. In this study, using batch bioassay techniques, the anammox toxicity of eight commonly occurring azole compounds was evaluated. The results show that 1H-benzotriazole and 5-methyl-1H-benzotriazole had the highest inhibitory effect on the anammox process, causing 50% decrease in anammox activity (IC₅₀) at concentrations of 19.6 and 17.8 mg L^-1, resp. 1H-imidazole caused less severe toxicity with an IC₅₀ of 79.4 mg L^-1. The other azole compounds were either nontoxic (1H-pyrazole, 1H-1,2,4-triazole and 1-methyl-pyrazole) or at best mildly toxic (1H-benzotriazole-5-carboxylic acid and 3,5-dimethyl-1H-pyrazole) towards the anammox bacteria at the concentrations tested. This study showed that most azole compounds tested displayed mild to low or no toxicity towards the anammox bacteria. The anammox bacteria were found to be far less sensitive to azoles compared to nitrifying bacteria.

Journal of Chemical Technology and Biotechnology 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, Safety of 1-Methylpyrazole.

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