Category: pyrazoles-derivatives

Mistico, Laetitia published the artcileAccess to Silylated Pyrazole Derivatives by Palladium-Catalyzed C-H Activation of a TMS group, Name: 1-Methylpyrazole, the publication is Chemistry – A European Journal (2016), 22(28), 9687-9692, database is CAplus and MEDLINE.

A simple and efficient approach to new silylated heterocycles of potential interest in medicinal chem. is presented. A set of bromophenyl trimethylsilyl pyrazole intermediates can be transformed by direct organometallic routes into two families of regioisomeric iodoaryl substrates; using either arylzinc or aryllithium chem., the TMS group remains on the pyrazole ring or translocates to the aryl moiety. These two families can then be efficiently transformed into benzo silino pyrazoles thanks to a single-step cyclization relying on the Pd-catalyzed activation of a nonactivated C(sp³)-H bond alpha to a Si atom. The exptl. conditions used, which are fully compatible with the pyrazole ring, suggest that this reaction evolves through a concerted metalation-deprotonation (CMD) mechanism.

Chemistry – A European 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 C4H6N2, Name: 1-Methylpyrazole.

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

Reiberger, Robert published the artcileSynthesis and In Vitro Evaluation of C-7 and C-8 Luteolin Derivatives as Influenza Endonuclease Inhibitors, Synthetic Route of 724710-02-5, the publication is International Journal of Molecular Sciences (2021), 22(14), 7735, database is CAplus and MEDLINE.

The part of the influenza polymerase PA subunit featuring endonuclease activity is a target for anti-influenza therapies, including the FDA-approved drug Xofluza. A general feature of endonuclease inhibitors is their ability to chelate Mg²⁺ or Mn²⁺ ions located in the enzyme′s catalytic site. Previously, we screened a panel of flavonoids for PA inhibition and found luteolin and its C-glucoside orientin to be potent inhibitors. Through structural anal., we identified the presence of a 3′,4′-dihydroxyphenyl moiety as a crucial feature for sub-micromolar inhibitory activity. Here, we report results from a subsequent investigation exploring structural changes at the C-7 and C-8 positions of luteolin. Exptl. IC₅₀ values were determined by AlphaScreen technol. The most potent inhibitors were C-8 derivatives with inhibitory potencies comparable to that of luteolin. Bio-isosteric replacement of the C-7 hydroxyl moiety of luteolin led to a series of compounds with one-order-of-magnitude-lower inhibitory potencies. Using X-ray crystallog., we solved structures of the wild-type PA-N-terminal domain and its I38T mutant in complex with orientin at 1.9 Å and 2.2 Å resolution, resp.

International Journal of Molecular Sciences 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 C3H5BN2O2, Synthetic Route of 724710-02-5.

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

Teske, Kelly A. published the artcileParallel Chemistry Approach to Identify Novel Nuclear Receptor Ligands Based on the GW0742 Scaffold, SDS of cas: 763120-58-7, the publication is ACS Combinatorial Science (2017), 19(10), 646-656, database is CAplus and MEDLINE.

We describe the parallel synthesis of novel analogs of GW0742, a peroxisome proliferator-activated receptor δ (PPARδ) agonist. For that purpose, modified reaction conditions were applied, such as a solid-phase palladium-catalyzed Suzuki coupling. In addition, tetrazole-based compounds were generated as a bioisostere for carboxylic acid-containing ligand GW0742. The new compounds were investigated for their ability to activate PPARδ mediated transcription and their cross-reactivity with the vitamin D receptor (VDR), another member of the nuclear receptor superfamily. We identified many potent PPARδ agonists that were less toxic than GW0742, where ∼65 of the compounds synthesized exhibited partial PPARδ activity (23-98%) with EC₅₀ values ranging from 0.007-18.2 μM. Some ligands, such as compound 32, were more potent inhibitors of VDR-mediated transcription with significantly reduced PPARδ activity than GW0742, however, none of the ligands were completely selective for VDR inhibition over PPARδ activation of transcription.

ACS Combinatorial Science 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 C2H4ClNO, SDS of cas: 763120-58-7.

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

Gummadi, Venkateshwar Rao published the artcileDiscovery of 7-azaindole based anaplastic lymphoma kinase (ALK) inhibitors: Wild type and mutant (L1196M) active compounds with unique binding mode, Related Products of pyrazoles-derivatives, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(17), 4911-4918, database is CAplus and MEDLINE.

We have identified a novel 7-azaindole series of anaplastic lymphoma kinase (ALK) inhibitors. Compounds 7b, 7m and 7n demonstrate excellent potencies in biochem. and cellular assays. X-ray crystal structure of one of the compounds (7k) revealed a unique binding mode with the benzyl group occupying the back pocket, explaining its potency towards ALK and selectivity over tested kinases particularly Aurora-A. This binding mode is in contrast to that of known ALK inhibitors such as Crizotinib and NVP-TAE684 which occupy the ribose binding pocket, close to DFG motif.

Bioorganic & Medicinal Chemistry Letters published new progress about 1415825-05-6. 1415825-05-6 belongs to pyrazoles-derivatives, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 1-(2-Fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, and the molecular formula is C16H20BFN2O2, Related Products of pyrazoles-derivatives.

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

Tomasik, Z. published the artcile1-o-Chlorophenyl-3-methyl-5-pyrazolone and its derivatives, SDS of cas: 14580-22-4, the publication is Roczniki Chemii (1928), 345-8, database is CAplus.

o-ClC₆H₄NHNH₂ condenses with AcCH₂CO₂Et to yield 1-o-chlorophenyl-3-methyl-5-pyrazolone, m. 199° (4-benzylidene derivative, m. 167°; 4-o-nitrobenzylidene derivative, m. 160°), which when condensed with o-O₂NC₆H₄CHO yields o-nitrophenylbis-[1-o-chlorophenyl-3-methyl-5-pyrazolonyl]methane, m. 249°.

Roczniki Chemii 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, SDS of cas: 14580-22-4.

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

Valecha, Sheela M. published the artcileSynthesis and characterization of manganese (II), cobalt (II), nickel (II), copper (II) and zinc (II) mixed ligand complexes with [(1-phenyl-3-methyl-5-hydroxopyrazol-4-yl) phenylimino]2′,3′ dimethylaniline and 2-hydroxy-1-naphthaldehyde, Application In Synthesis of 4551-69-3, the publication is Acta Chimica Pharmaceutica & Indica (2015), 5(1), 16-21, database is CAplus.

Mixed ligand complexes of the type [MLL′] where M = Mn (II), Co (II), Ni (II), Cu (II), Zn (II) HL = [(1-phenyl-3-methyl-5-hydroxopyrazol-4-yl)phenylimino]2,3-dimethylaniline; (HPMPZP)dma. HL′= 2-hydroxy-1-naphaldehyde; (HNA), have been synthesized and characterized on the basis of elemental anal., conductivity measurements, magnetic, electronic and infra red spectral studies. The complexes confirm to 1:1:1 stoichiometry and are non electrolytes. The schiff base HL act as a monovalent bidentate ligand co-ordinating through azomethine nitrogen and phenolic oxygen. On the basis of electronic spectra, IR spectra and magnetic moment measurements; six coordinated octahedral structures have been proposed for the complexes. Thermal studies revealed the presence of two coordinated water mols. The shiff base and mixed ligand complexes have been tested for their antibacterial activity against the Escherichia coli, Bacillus substilis, staphylococcus aureus.

Acta Chimica Pharmaceutica & Indica 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 C24H12, Application In Synthesis of 4551-69-3.

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

van Alphen, J. published the artcileThe reaction between α-halogen ketones and derivatives of phenylhydrazine. I. The reactivity of the N:NC:C group in α-phenylazocrotonic acid esters, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, the publication is Recueil des Travaux Chimiques des Pays-Bas et de la Belgique (1945), 109-14, database is CAplus.

α-Phenylazocrotonic acid (I) Et ester, prepared from 16.5 g. ClCH₂CO₂Et (II) in 60 ml. EtOH mixed with cooling with 10.8 g. PhNHNH₂ in 100 ml. EtOH and 13.6 g. crystallized NaOAc in 30 ml. H₂O, seps. as red needles, m. 51°. After a long time 1-phenyl-3-methyl-4-phenylazo-5-pyrazolone (III), m. 158°, seps. from the mother liquor. I Me ester, prepared in the same manner, m. 46° (from EtOH). When the Et ester was ozonized in CHCl₃ at 0°, then decomposed with ice and CaCO₃, the CHCl₃ layer contained an oil which was reduced in EtOH with Al-Hg, yielding PhNHNHAc, thus proving the structure of I. Reduction of I (Raney Ni, H) yielded 4,4′-bi[1-phenyl-3-methylpyrazolone] (IV), which, boiled with FeCl₃, gave the characteristic blue color of “pyrazolone blue” in CHCl₃. I reduced in EtOH (Al-Hg) yielded 1-phenyl-3-methyl-5-pyrazolone (V). Bromination of I yielded tars. Bromination in small amounts in Et₂O yielded 1-(4-bromophenyl)-3-methyl-4-bromo-5-pyrazolone, m. 171°. Me ester of I yielded the same product. Et ester of I reacted in dry Et₂O with HCl to give a salt which, boiled with H₂O, yielded 1-phenyl-3-methyl-4-chloro-5-pyrazolone (VI), m. 153°. Me ester of I yielded the same product. Heating VI with PhNHNH₂ yielded III. That the Cl had not entered the ring was shown by the preparation of 1-(4-chlorophenyl)-3-methyl-5-pyrazolone, m. 168°, and 1-(2-chlorophenyl)-3-methyl-5-pyrazolone, m. 109°. Et acetoacetate p-chlorphenylhydrazone, yellow needles, m. 111°. PhMgBr added to I gave a complex mixture of unidentifiable products. I does not add to maleic anhydride.

Recueil des Travaux Chimiques des Pays-Bas et de la Belgique 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 C25H47NO8, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone.

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

Venturella, Pietro published the artcileReactivity of the flavanone nucleus. II. Effect of substituents on the reaction with phenylhydrazine, Computed Properties of 13599-22-9, the publication is Annali di Chimica (Rome, Italy) (1961), 759-68, database is CAplus.

cf. CA 55, 15467b. Substituents in the flavanone nucleus do not particularly affect the conversion of their phenylhydrazones into pyrazoline derivatives The possibility to isolate the intermediate phenylhydrazones depends on the nature and the position of the substituents. The appropriate flavanone (0.5 g.) in 10 cc. 95% EtOH refluxed 1 hr. with 0.3 g. PhNHNH₂, kept some time, and diluted with H₂O gave the corresponding phenylhydrazone. In this manner were prepared the following compounds: 2-(p-methoxyphenyl)flavanone phenylhydrazone (I); 2-[3,4-(CH₂O₂)C₆H₃] analog (II) of I, m. 127-8°; 2-(3,4-methyl-enedioxyphenyl)-5,6,8-trimethoxyflavanone phenylhydrazone (III) (without EtOH), m. 129-31°; 2-Ph analog of III; 2-phenyl-6-methoxyflavanone phenylhydrazone (IV); and the 5,6-di-MeO analog of IV, needles, m. 118-20°. The appropriate flavanone (0.5 g.) and excess PhNHNH₂ heated a few min. in a test tube over a free flame, cooled, dissolved in AcOH, and poured into H₂O gave the corresponding 3,5-diarylpyrazoline (V). The appropriate flavanone (0.5 g.) in 5 cc. AcOH refluxed 1 hr. with 0.3 g. PhNHNH₂, cooled, and diluted with H₂O gave the corresponding V. The appropriate chalcone (0.2 g.) and PhNHNH₂ heated a few min. in a test tube over a free flame, dissolved in AcOH, and poured into H₂O gave the corresponding V. The appropriate phenylhydrazone refluxed 1 hr. with AcOH gave the corresponding V. The appropriate V refluxed with Ac₂O and NaOAc gave the corresponding acetate which fluoresces in EtOH intensely blue-green. By these methods were prepared the following V and their acetates (3- and 5-aryl group, crystal form, and m.p., and m.p. of acetate given): o-HOC₆H₄, p-MeOC₆H₄ (Va), needles, 168-9°, 132-3°; o-HOC₆H₄, 3,4-(CH₂O₂)C₆H₃ (VI), needles, 145-6°, 116-17°; 2,3,5,6-HO(MeO)₃C₆H, 3,4-(CH₂O₂)C₆H₃ (VIa), needles, 185-6°, 195-6°, 2,3,5,6-HO(MeO)₃C₆H, Ph (VII), yellow-green plates, 193-4°, 132-3°; 2,5-HO(MeO)C₆H₃, Ph (VIII), needles, 150-1°, 114-15°; 2,5,6-HO(MeO)₂C₆H₂, Ph (IX), yellow plates, 147-8°, 147°, VII or VIII or IX (1 g.) in 30 cc. refluxing 5% aqueous NaOH treated gradually with 6.5 g. KMnO₄ in 70 cc. H₂O, refluxed 3 hrs., and worked up gave 1,5-diphenyl-3-pyrazolecarboxylic acid, m. 183-5° (EtOH). Va or VI, or Via oxidized similarly with 8 g. KMnO₄ in 100 cc. H₂O gave 1-phenyl-3,5-pyrazoledicarboxylic acid, platelets, m. 265-6° (H₂O). The ultraviolet absorption spectra of the various pyrazolines, and II, III, and V, and the infrared absorption spectra of VI and its acetate are recorded.

Annali di Chimica (Rome, Italy) published new progress about 13599-22-9. 13599-22-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Carboxylic acid,Benzene, name is 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid, and the molecular formula is C12H10O4S, Computed Properties of 13599-22-9.

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

Liu, Deng-Feng published the artcileRing-opening copolymerization of epoxides and anhydrides using manganese(III) asymmetrical Schiff base complexes as catalysts, Formula: C17H14N2O2, the publication is RSC Advances (2015), 5(5), 3854-3859, database is CAplus.

Based on a series of asym. Schiff base H₂Lⁿ (n = 1-4) ligands with different electronic and steric effects, a series of [Mn(Lⁿ)Cl] complexes were obtained and shown to be effective catalysts in cyclohexene oxide and maleic anhydride, cyclohexene oxide and phthalic anhydride, styrene oxide and maleic anhydride or styrene oxide and phthalic anhydride ring-opening copolymerizations Through the structure design, the input of the electron-withdrawing Br substituent para to the phenoxide group of the complexes is quite beneficial to the improved activities. Moreover, both steric and electronic effects of a suitable MeO substituent at the ortho position of the phenoxide group have much more influence on the formation of alternating ring-opening copolymers than that of selected reaction conditions.

RSC Advances 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, Formula: C17H14N2O2.

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

Liu, Deng-Feng published the artcileRing-opening copolymerization of epoxide and dianhydride in the presence of manganese(III) asymmetrical bis-Schiff base catalysts, Related Products of pyrazoles-derivatives, the publication is Canadian Journal of Chemistry (2014), 92(11), 1098-1105, database is CAplus.

Based on a series of asym. bis-Schiff base H₂Lⁿ (n = 1-4) ligands with different electronic and steric effects, a series of [Mn(Lⁿ)Cl] complexes 1-4 are obtained and shown to be effective catalysts in ring-opening copolymerization of epoxides and dianhydrides. Through the structure design, the input of electron-withdrawing bromine substituent para to the phenoxide group of the complexes is considerately beneficial to the improved activities. Moreover, steric and electronic effects of the suitable MeO substituent at the ortho orientation on the phenoxide group may both play a role in the formation of alternating ring-opening copolymers under the identical reaction conditions. In three cocatalysts tested, n-Bu₄NBr is pos. to monomer conversion and chain growth of polymer.

Canadian 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 C17H14N2O2, Related Products of pyrazoles-derivatives.

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