pyrazoles-derivatives

Yang, Zhong-Tao published the artcileOrganocatalytic Enantioselective aza-Friedel-Crafts Reactions of Pyrazolinone Ketimines with Hydroxyindoles and Electron-Rich Phenols, Related Products of pyrazoles-derivatives, the publication is Advanced Synthesis & Catalysis (2018), 360(10), 2049-2054, database is CAplus.

A variety of enantioenriched indole derivatives substituted in the benzene ring were synthesized via an organocatalytic asym. aza-Friedel-Crafts reaction of pyrazolinone ketimines with hydroxyindoles. This reaction was also applicable to electron-rich phenols, yielding the desired products in high yields (up to 99%) and excellent stereo-selectivities (91-99% ee). Moreover, this method presents its potential in the synthesis of structurally novel indole-pyrazolinone conjugate derivatives

Advanced Synthesis & Catalysis 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 C12H23N3S, Related Products of pyrazoles-derivatives.

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

Ma, Jing published the artcileElectrochemical-Induced C(sp³)-H Dehydrogenative Trimerization of Pyrazolones to Tripyrazolones, Computed Properties of 14580-22-4, the publication is European Journal of Organic Chemistry (2021), 2021(40), 5491-5496, database is CAplus.

The electrochem.-induced three-component C(sp³)-H dehydrogenative trimerization of pyrazolones to tripyrazolones with hydrogen evolution has been accomplished under the metal- and external-oxidant-free conditions. This protocol provides an efficient and eco-friendly method for the synthesis of tripyrazolones, which avoids the use of metals and stoichiometric chem. oxidants. A wide range of functional groups was tolerated to give selectively the desired products in high yields. Importantly, such an electrochem.-oxidation-induced dehydrogenative trimerization reaction could be easily scaled up with excellent efficiency.

European Journal of Organic 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 C10H9ClN2O, Computed Properties of 14580-22-4.

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

Sun, Pengfei published the artcileDMSO-promoted regioselective synthesis of sulfenylated pyrazoles via a radical pathway, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, the publication is Organic Chemistry Frontiers (2017), 4(7), 1367-1371, database is CAplus.

A green and eco-friendly protocol for the construction of C-4 sulfenylated pyrazoles I [R¹ = Me, t-Bu, Ph, COOH; R² = Me, Ph, 4-MeC₆H₄, 4-ClC₆H₄, 2-ClC₆H₄; R³= Ph, 4-MeC₆H₄, 4-ClC₆H₄, etc.; R⁴ = OH] via a radical pathway was established for the first time. When 1,3-diphenyl-1H-pyrazol-5-amine was reacted with aryl thiols the corresponding 2,5-diphenyl-4-arylsulfanyl-pyrazol-3-amines I [R¹ = R² = Ph; R³ = 4-MeC₆H₄, 4-MeOC₆H₄, 4-BrC₆H₄; R⁴ = NH₂] were also obtained in moderate to good yields. The reaction worked smoothly under catalyst and solvent-free conditions to afford wide range of sulfenylated pyrazole derivatives in good to excellent yields. The thiyl free radical generated in situ, served as a single electron transfer medium for the present transformation. This reaction provided a new strategy for the formation of C-S bond.

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 C13H10O3, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone.

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

Almendros, Pedro published the artcileTransition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles, Recommanded Product: 1-Methylpyrazole, the publication is Organic Chemistry Frontiers (2018), 5(21), 3163-3169, database is CAplus.

Several heterocycles reacted with shelf-stable 2-(2-fluoropyridinium-1-yl)-1,1-bis[(trifluoromethyl)sulfonyl]ethan-1-ide, a latent Tf₂C=CH₂ source, to give rise in a mild and controllable way to adducts via direct C-H bis[(trifluoromethyl)sulfonyl]ethylation reactions. This metal- and irradiation-free protocol is convenient. Besides, the volatile side-product 2-fluoropyridine can be smoothly eliminated under vacuum, which facilitates purification The substrate scope survey discloses that exquisite chemo- and regioselectivities are achieved in a variety of heterocyclic systems. Of particular interest are the late-stage structural modification of known pharmaceuticals, such as the marketed drugs phenazone (antipyrine) and edaravone, and the development of a water soluble fluorescent dye.

Organic Chemistry Frontiers 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

Oka, Naoki published the artcileAryl Boronic Esters Are Stable on Silica Gel and Reactive under Suzuki-Miyaura Coupling Conditions, Name: 1H-Pyrazole-4-boronic acid, the publication is Organic Letters (2022), 24(19), 3510-3514, database is CAplus and MEDLINE.

A wide range of aryl boronic 1,1,2,2-tetraethylethylene glycol esters [ArB(Epin)s] were readily synthesized. Purifying aryl boronic esters by conventional silica gel chromatog. is generally challenging; however, these introduced derivatives were easily purified on silica gel and isolated in excellent yields. The purified ArB(Epin) was subjected to Suzuki-Miyaura couplings, which provided higher yields of the desired biaryl products than those obtained using the corresponding aryl boronic acids or pinacol esters.

Organic 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, Name: 1H-Pyrazole-4-boronic acid.

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

Abu Talip, Ruwaida Asyikin published the artcileUnderstanding the physicochemical and transport properties of pyrazolium based ionic liquids bearing iodide and triiodide anions, Category: pyrazoles-derivatives, the publication is Journal of Molecular Liquids (2022), 118270, database is CAplus.

Ionic liquids (ILs) particularly imidazolium-based ILs have been widely used in various industrial applications such as solvent or catalyst for synthesis, as electrolyte in energy devices, and as solvent for extraction and separation The extensive phys. and chem. properties data available on the imidazolium-based ILs have made them easier to be incorporated into variety of applications compared to other types of ionic liquids Ionic liquids composed of pyrazolium derivative as cation having the same heteroaromatic ring structure with imidazolium derivative except for the position of the nitrogen atoms, may result in unique phys. and chem. properties, yet have been minimally explored. The main objective of this study is to investigate the physicochem. and transport properties of pyrazolium-based ILs to fully comprehend their potential for further development for a specific task or application. In this study, three alkylpyrazolium iodides ILs as well as corresponding three alkylpyrazolium triiodides ILs were synthesized and characterized. The NMR anal. showed that the formation of alkylpyrazolium triiodides ILs from their resp. iodide precursors has resulted the resonance to be more deshielded due to lesser electron d. experienced by the acidic protons of pyrazolium cation due to the weakly localized charge in triiodide anion. The effect of different anions and the alkyl chain of the pyrazolium cation moiety has a pronounced effect on the phys. and transport properties of the synthesized ILs. It is found that the pyrazolium ionic liquids with triiodide anion demonstrated high thermal stability, low viscosity, and high ionic conductivity as compared to the iodide analogs.

Journal of Molecular Liquids 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, Category: pyrazoles-derivatives.

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

Valsalakumari, Remya published the artcileMechanism of cellular uptake and cytotoxicity of paclitaxel loaded lipid nanocapsules in breast cancer cells, Recommanded Product: 4-(5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide, the publication is International Journal of Pharmaceutics (Amsterdam, Netherlands) (2021), 120217, database is CAplus and MEDLINE.

Lipid nanocapsules (LNCs) have proven their efficacy in delivering different drugs to various cancers, but no studies have yet described their uptake mechanisms, paclitaxel (PTX) delivery or resulting cytotoxicity towards breast cancer cells. Herein, we report results concerning cellular uptake of LNCs and cytotoxicity studies of PTX-loaded LNCs (LNCs-PTX) on the three breast cancer cell lines MCF-7, MDA-MB-231 and MDA-MB-468. LNCs-PTX of sizes 50 ± 2 nm, 90 ± 3 nm and 120 ± 4 nm were developed by the phase inversion method. Fluorescence microscopy and flow cytometry were used to observe the uptake of fluorescently labeled LNCs and cellular uptake of LNCs-PTX was measured using HPLC analyses of cell samples. These studies revealed a higher uptake of LNCs-PTX in MDA-MB-468 cells than in the other two cell lines. Moreover, free PTX and LNCs-PTX exhibited a similar pattern of toxicity towards each cell line, but MDA-MB-468 cells appeared to be more sensitive than the other two cell lines, as evaluated by the MTT cytotoxicity assay and a cell proliferation assay based upon [3H]thymidine incorporation. Studies with inhibitors of endocytosis indicate that the cellular uptake is mainly via the Cdc42/GRAF-dependent endocytosis as well as by macropinocytosis, whereas dynamin-dependent processes are not required. Furthermore, our results indicate that endocytosis of LNCs-PTX is important for the toxic effect on cells. Western blot anal. revealed that LNCs-PTX induce cytotoxicity by means of apoptosis in all the three cell lines. Altogether, the results demonstrate that LNCs-PTX exploit different mechanisms of endocytosis in a cell-type dependent manner, and subsequently induce apoptotic cell death in the breast cancer cells here studied. The article also describes biodistribution studies following i.v. injection of fluorescently labeled LNCs in mice.

International Journal of Pharmaceutics (Amsterdam, Netherlands) 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 C12H9N3O4, Recommanded Product: 4-(5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide.

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

Tong, Chao-Lai published the artcileNucleophilic and Radical Heptafluoroisopropoxylation with Redox-Active Reagents, SDS of cas: 1289010-13-4, the publication is Angewandte Chemie, International Edition (2021), 60(42), 22915-22924, database is CAplus and MEDLINE.

The practical and efficient heptafluoroisopropoxylation reactions through the invention of a series of redox-active N-OCF(CF₃)₂ reagents e.g., I were described. These reagents were readily prepared from the oxidative heptafluoroisopropylation of hydroxylamines e.g., II with AgCF(CF₃)₂. The substitutions on the nitrogen atom significantly affected the properties and reactivities of N-OCF(CF₃)₂ reagents. Accordingly, two types of N-OCF(CF₃)₂ reagents including I and III were used as OCF(CF₃)₂ anion and radical precursors, resp. This protocol enables the direct heptafluoroisopropoxylation of a range of substrates, delivering the corresponding products in moderate to excellent yields.

Angewandte Chemie, International Edition published new progress about 1289010-13-4. 1289010-13-4 belongs to pyrazoles-derivatives, auxiliary class Pyrazoles, name is 4,6-Dichloro-2-(3-methyl-1H-pyrazol-1-yl)pyrimidine, and the molecular formula is C11H14O2, SDS of cas: 1289010-13-4.

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

Yan, Xingchen published the artcileProteasome inhibition and cytostatic effects on human cancer cells by pyrazolone-enamines: a combined crystallographic, structural and computational study, Application In Synthesis of 4551-69-3, the publication is New Journal of Chemistry (2015), 39(3), 2168-2180, database is CAplus.

Nine compounds were designed and synthesized by the condensation reaction of the carbonyl in 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one (HPMBP) with the amino groups in 5-aminoisophthalic acid, 4,4′-diaminodiphenylmethane, 4-aminophenylacetic acid, 4-aminobenzamide, 2-amino-4-methylphenol, 5-amino-2-methylphenol, 2-aminophenol, 3-aminophenol and 4-aminophenol. They were then characterized by IR, ¹H NMR, elemental anal., and x-ray crystallog., which suggested that all of them exist as the pyrazolone-enamine forms in the solid state and in a DMSO solution through tautomeric reactions. The nine compounds were evaluated for their ability to inhibit the proliferation of human liver cancer HepG2 cells. Compounds 4-[(Z)-(2-Hydroxy-5-methylphenylamino)phenylmethylene]-3-methyl-1-phenyl-2-pyrazolin-5-one (5), 4-[(Z)-(3-Hydroxy-4-methylphenylamino)phenylmethylene]-3-methyl-1-phenyl-2-pyrazolin-5-one (6), 4-[(Z)-(2-Hydroxyphenylamino)phenylmethylene]-3-methyl-1-phenyl-2-pyrazolin-5-one (7) and 4-[(Z)-(3-Hydroxyphenylamino)phenylmethylene]-3-methyl-1-phenyl-2-pyrazolin-5-one (8) demonstrated a strong inhibitory effect on the proliferation of HepG2 cells. The nine compounds can also inhibit the activity of the human cancer cellular 20S proteasome. Further studies on compound (6) as the representative indicate that it can cause the accumulation of ubiquitinated proteins and the proteasome target proteins Bax and p27, and exhibit a cytostatic effect in HepG2 cells in a concentration-dependent and time-dependent manner. The four potential tautomers of compound (6) were optimized and their single point energies were calculated by the d. functional theory (DFT) B3LYP method based on the polarized continuum model (PCM) in water to identify the most likely tautomer existing in cancer cells. Based on the optimized structure of the most stable tautomer in water, the Wiberg bond orders, mol. electrostatic potential (MEP) maps and frontier MO were calculated As compounds (5), (6), (7) and (8) have hydroxyl in the ortho-position or meta-position, the authors’ study can provide some information to study their anticancer mechanism and the substitution effect of different functional groups.

New Journal of 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 C19H15NO3, Application In Synthesis of 4551-69-3.

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

Wu, Gengxin published the artcileAsymmetric Organocatalysis Combined with Palladium Catalysis: Synergistic Effect on Enantioselective Mannich/α-Allylation Sequential Reactions of Pyrazolones in Constructing Vicinal Quaternary Stereocenters, Product Details of C10H9ClN2O, the publication is Organic Letters (2019), 21(19), 7708-7712, database is CAplus and MEDLINE.

In this letter, an efficient one-pot asym. sequential reaction is achieved by organo/transition metal relay catalysis in constructing two consecutive C-C bonds, which involves enantioselective amino squaramide catalytic Mannich-type addition of pyrazolones to isatin-derived ketimines and a subsequent palladium catalyzed diastereoselective allylic alkylation of pyrazolones with allylic acetates. An array of novel pyrazolone-aminooxindole-propylene structural motifs are obtained in a high level of yield and with excellent enantio- and diastereoselectivity (up to 95% yield, >20:1 dr, >99% ee). This methodol. features the formation of vicinal quaternary carbon-stereocenters, and the second all-carbon tetrasubstituted stereogenic center is induced by joint action of the achiral palladium catalysis and the chiral environment generated from the Mannich step. Moreover, the usefulness of this methodol. is highlighted by converting the allylic product into the carbonyl compound

Organic Letters 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 C15H14Cl2S2, Product Details of C10H9ClN2O.

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