Tag: M.W=250-300

Finar, I. L. published the artcilePreparation and properties of some bipyrazolyls, Application of 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid, the publication is Journal of the Chemical Society (1955), 1205-8, database is CAplus.

The synthesis of 5,5′-dimethyl-1,1′-diphenyl-(I) and 1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl (II) was repeated, and the 3,5′-isomer (III) of the latter was isolated. Evidence was given for the orientations of these two isomers, and some 4,4′-disubstituted derivatives of I, II, and III were prepared (CO₂Et)₂ (IV) (36.5 g.) and 29 g. dry Me₂CO were added during 25 min. to NaOMe (from 12.5 g. Na) under Et₂O at 0°, the mixture was stirred for 2 days to give 21-38% octane-2,4,5,7-tetraone (V), yellow needles, m. 120-1° (from MeOH). IV (36.5 g.) and 1/2 of 16 g. PhCOMe were similarly treated, the other 1/2 added 4 hrs. later, and the mixture stirred 3 days to give 62-74% 1,6-diphenylhexane-1,3,4,6-tetraone (VI), yellow needles, m. 177-9°. V (3.4 g.) was heated with 4.3 g. PhNHNH₂ in HOAc for 1 hr. to give 3.4 g. I, buff needles, m. 141-2°. VI (47.2 g.) was similarly treated 3-4 hrs. with 34.6 g. PhNHNH₂ to give 35.2 g. II, m. 233°. The filtrate was diluted with H₂O and then crystallized to yield 12.2 g. III, white needles, m. 135-6°. VI (58.8 g.) in HOAc was treated during 2.75 hrs. with 21.6 g. PhNHNH₂ in HOAc, heated for a further 1.25 hrs., and set aside for 2 days to give after fractional crystallization unchanged starting material, II, and 3-(α-benzoylacetyl)-1,5-diphenylpyrazole (VII), yellow needles, m. 164-6.5°. VII on oxidation with alk. KMnO₄ yielded 1,5-diphenylpyrazole-3-carboxylic acid (VIII), m. 185-6°. VII (2.9 g.) and 0.97 g. PhNHNH₂ in HOAc heated 1 hr., and kept at room temperature overnight gave 2.4 g. II and 1 g. III. The infrared spectra of II and III were complex and similar. In general, the lowering of the symmetry as in III increases the number of bands. III in the 1600-650 cm.^-1 region had 25 strong bands. Bischler’s method [Ber. 25, 3143(1892)] of preparing VIII was modified as follows: MeCOCH₂CO₂Et (30 g.) was refluxed 6 hrs. with 5.4 g. Na wire under Et₂O, then 46 g. BzCH₂Br in Et₂O was added to maintain gentle reflux, then refluxed 2 hrs., and set aside overnight to give 56 g. AcCH(CH₂Bz)CO₂Et (IX) as a red oil. IX (12.4 g.) in EtOH was treated in the cold with 4.65 g. PhN₂Cl, and then 16.4 g. NaOAc in H₂O, the mixture set aside 24 hrs. in ice, and the oil which separated heated 15 min. with 6 g. NaOH in a little H₂O to give 6.7 g. VIII. I in CHCl₃ was treated with Br at room temperature to yield 4,4′-dibromo-5,5′-dimethyl-1,1′-diphenyl-3,3′-bipyrazolyl, rods, m. 159-60°. 4,4′-Dibromo-1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl, plates, m. 272-3°. 4,4′-Dibromo-1,1′,3′,5-tetraphenyl-3,5′-bipyrazolyl, white rosettes, m. 200-1°. II (13.2 g.) in HOAc and 26 cc. concentrated HCl was heated 2 hrs. with 2.4 g. paraformaldehyde to give the 4,4′-bis(chloromethyl) derivative, white needles, (6.2 g.), m. 274-6°. I (3.14 g.) in HOAc was heated 0.5 hrs. with 6.37 g. HgAc₂ to yield 4.8 g. 4,4′-bis(acetoxymercuri) compound (X), white needles, m. 204-4.5° (aqueous HOAc). II (4.38 g.) similarly treated yielded after 5 hrs. refluxing 7.6 g. 4,4′-bis(acetoxymercuri)-1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl (XI), white powder, m. 271.5°. The mercuri compounds when treated with HOAc and Br at room temperature gave the corresponding 4,4′-di-Br compounds X refluxed with dilute HCl gave I; however, XI had to be refluxed for some time with HOAc containing concentrated HCl before II could be obtained.

Journal of the Chemical Society 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 C16H12N2O2, Application of 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid.

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

Roy, Sutapa published the artcileSynthesis, characterization and 3-D molecular modeling of some oxovanadium(IV) complexes involving O₂N₂ donor core, SDS of cas: 4551-69-3, the publication is Journal of Pharmacy and Chemistry (2014), 8(4), 9-13, database is CAplus.

In view of the wide application of vanadium complexes, oxovanadium(IV) complexes involving pyrazolone-based aroylhydrazone and 8-hydroxyquinoline were synthesized and characterized by different physicochem. studies such as elemental anal., molar conductance, magnetic measurements, IR, TGA, ESR, mass and electronic spectral studies. The overall exptl. data based from all the studies presented suggests the complexes under present investigation are [VO(L)(8-hq)(H₂O)], where LH- pyrazolone-based aroylhydrazone and 8-hqH = 8-hydroxyquinoline, involving a monobasic didentate (O,N) donor ligand. An octahedral structure with axial oxo groups are proposed for these complexes.

Journal of Pharmacy and 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, SDS of cas: 4551-69-3.

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

Bie, Hong-Yan published the artcileCrystal structure of (4Z)-4-((2-(methylamino)phenylamino)(phenyl)methylene)- 3-methyl-1-phenyl-1H-pyrazol-5-(4H)-one, C₂₄H₂₂N₄O, Application In Synthesis of 4551-69-3, the publication is Zeitschrift fuer Kristallographie – New Crystal Structures (2014), 229(1), 17-18, database is CAplus.

The crystal structure of the title compound is herein given. The title compound was synthesized from of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone and N-methylbenzene-1,2-diamine. The Schiff base has a Z configuration about the double bound and shows hydrogen bonding.

Zeitschrift fuer Kristallographie – New Crystal Structures 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, Application In Synthesis of 4551-69-3.

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

Liu, Jiang published the artcileRing-opening copolymerization of CHO and MA catalyzed by the asymmetrical Cr(III)-bis-Schiff-base complex, Application of 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, the publication is Inorganic Chemistry Communications (2017), 86-88, database is CAplus.

Using an asym. Cr(III)-bis-Schiff-base complex [Cr(L)Cl] (1; H₂L obtained from condensation of 5-bromo-salicylaldehyde and HL⁰ (Z)-4-((2-aminophenylimino)(phenyl)methyl)-3-methyl-1H-pyrazol-5(4H)-one) as the catalyst, bulk solvent-free ring-opening copolymerization of CHO (cyclohexene oxide) and MA (maleic anhydride) in the presence of cocatalyst DMAP (4-(dimethylamino)-pyridine) was effectively realized, in which, on the condition of low 1/DMAP concentration for a controllable polymerization, perfectly alternating polyester while not poly(ester-coether) could be obtained.

Inorganic Chemistry Communications 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, Application of 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

Ma, Xue-lin published the artcileCondensation reaction of aromatic aldehydes and 1-phenyi-3-methyl-4-benzoyl-pyrazolone catalysted by phosphotungstic acid loaded on 404 organic support, Name: 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, the publication is Huaxue Shiji (2014), 36(7), 646-650, database is CAplus.

Many loaded-catalysts are applied to the Mannich reaction, but they have disadvantages such as low yield, unstability of loaded rate and asking for long time. 404 Organic support loaded phosphotungstic acid was synthesized by the reaction of 404 organic support and phosphotungstic acid in CC14. The effects of different reaction conditions on the yields were investigated. The condensation reaction of aromatic aldehydes and 1-phenyl-3-methyl-4-benzoyl-pyrazolone was catalyzed by 404 organic support loaded phosphotungstic acid. Simultaneously the products were determined by IR, ¹HNMR and elemental anal. The catalyst was provided with stable cubic crystal spatial structure and good dispersion. This protocol has advantages of stability of loaded rate, short time, mild condition, high yield, high selectivity, simple work-up, environmental friendly procedure and the catalyst can be reused.

Huaxue Shiji 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, Name: 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

Li, He published the artcileStructural diversity and properties of four complexes with 4-acyl pyrazolone derivative, Recommanded Product: 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, the publication is Polyhedron (2013), 209-215, database is CAplus.

Four {[Zn(HL)(H₂O)(DMF)](NO₃)}_n (1), [Cd(HL)₂]_n (2), {[Mn(HL)₂]·MeCN·2H₂O} (3) and {[Mn(L)(μ₂-EtOH)]}_n (4) (H₂L = N-(1-phenyl-3-methyl-4-benzal-pyrazolone-5)-nicotinic hydrazide) were synthesized and characterized by elemental analyses, IR spectra, thermal analyses and single crystal x-ray diffraction. The structural analyses reveal that complexes 1, 2 and 3, formed by H₂L with metal nitrate, have Zigzag chain, double-stranded chain and mononuclear structures, resp., and the ligands adopt three different coordination modes in these complexes. While, complex 4, formed by H₂L with Mn acetate, represents a 2-dimensional network structure with dinuclear units bridged by EtOH mols. The metal atom and counteranion have certain influences on the structures of resulting complexes. The fluorescent properties of 1 and 2 and the magnetism of 4 were studied.

Polyhedron 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, 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

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

Dong, W.-K. published the artcileSynthesis, crystal, and supermolecular structure of (Z)-4-({4-[1-(hydroxyimino)ethyl]-phenylimino}(phenyl)methyl)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, Application In Synthesis of 4551-69-3, the publication is Asian Journal of Chemistry (2013), 25(17), 9952-9956, database is CAplus.

The compound, (Z)-4-({4-[1-(hydroxyimino)ethyl]phenylimino}(phenyl)methyl)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one was synthesized and characterized by elemental anal., IR spectra and X-ray diffraction method [triclinic, space group P-1, a 9.5375(12), b 11.2824(13), c 20.545(2) Å, α 97.3970(10), β 92.0430(10), γ 99.280(2)°, V 2160.1(4) ų, Z 4]. This compound is a potential tridentate ligand containing mono-oxime group. In the crystal structure, there are two crystallog. independent but chem. identical mols. A and B. There are two strong intramol. N3-H3…O1 and N7-H7…O3 hydrogen bonds form six-membered S(6) ring motifs. Each mol. A interlinks two neighboring mols. B into a 1D infinite chain through six intermol. O2-H2…N6, C29-H29A…O2, C35-H35…N4, O4-H4…N2, C4-H4A…O4 and C10-H10…N8 hydrogen bonds and each mol. B interlinks two neighboring mols. A into the other 1D infinite chain in the same way. Furthermore, the two dual chains are further stabilized by intermol. C50-H50B…O1 hydrogen bonds to form an infinite 2D supramol. network structure.

Asian 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, Application In Synthesis of 4551-69-3.

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

Li, Tianrong published the artcileA rhodamine 6G derivative as “turn-on” fluorescent probe for Cu²⁺. Spectroscopy, single crystal structure and DFT calculations, Application of 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, the publication is Polyhedron (2017), 154-159, database is CAplus.

In order to achieve an effective “turn-on” fluorescence detection of Cu²⁺, a rhodamine 6G-based sensor [1-phenyl-3-methyl-5-hydroxypyrazole-4-benzoyl(rhodamine 6G) hydrazone, 1] was prepared Fluorescence and UV-Vis absorption titration, detection limit, single crystal structure, binding mode, and quantum mech. calculation studies were also discussed in detail. Sensor 1 showed highly selectivity and sensitivity to Cu²⁺ among common cations (Na⁺, K⁺, Mg²⁺, Ca²⁺, Mn²⁺, Co²⁺, Ni²⁺, Zn²⁺, Cd²⁺, Cr³⁺, Fe³⁺ and Cu²⁺) in acetonitrile. Upon addition of Cu²⁺, a new absorption band at 523 nm, and a strong emission band centering at 557 nm appeared in 1 solution Relevant solution changed from colorless to purple, and an obvious orange fluorescence emission was given. A maximum fluorescence enhancement of 250 times at 557 nm could be made by addition of 6 equiv of Cu²⁺. The fluorescence detection limit was calculated to be 2.5 μM (0.20 ppm) for Cu²⁺, and 1:1 stoichiometry between Cu²⁺ and 1 was proved. In the single crystal of 1-Cu²⁺ complex, rhodamine moiety exhibited an open cycle form. We believe 1 can be a good candidate for the fluorescence detection of Cu²⁺.

Polyhedron 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, Application of 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

Persson, Tobias published the artcilePyrazole carboxamides and carboxylic acids as protein kinase inhibitors in aberrant eukaryotic signal transduction: Induction of growth arrest in MCF-7 cancer cells, Quality Control of 13599-22-9, the publication is Organic & Biomolecular Chemistry (2007), 5(24), 3963-3970, database is CAplus and MEDLINE.

Densely functionalized pyrazolecarboxamides, e.g. I, and pyrazolecarboxylic acids were prepared through saponification and transamidation of ester-functionalized pyrazoles. This synthetic protocol allowed for three diversifying steps in which appendages on the pyrazole scaffold were adjusted to optimize inhibition of protein kinases. Thirty-five analogs were tested in CK2, AKT1, PKA, PKCα, and SAPK2a (p38) kinase inhibition bioassays. Blocking of these kinases may lead to effective therapies for treating inflammatory diseases and cancer. In order to investigate potential biol. activity, MCF-7 human breast cancer cells were incubated with the most promising derivatives Two analogs caused changes in MCF-7 cell growth, one of them through cell cycle arrest demonstrated by cell cycle anal.

Organic & Biomolecular Chemistry 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 C16H12N2O2, Quality Control of 13599-22-9.

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