- Supramolecular structure of 1-phenyl-3-methyl-4-benzoylpyrazolon-5-one
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The compound 1-phenyl-3-methyl-4-benzoylpyrazolon-5-one with the molecular formula C17H14N2O2, exists in a keto-enamine tautomeric form. The pyrazolone ring makes dihedral angles of 28.36(3) and 59.31(5) with the two phenyl rings. The molecules are linked into twodimensional supramolecular structure by a combination of N-H···O and C-H···O hydrogen-bonding interactions.
- Xu, Li,Wang, Zheng-Kun,Sun, Yin-Xia,Zhang, Yu-Jie,Dong, Xiu-Yan
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- Copper(II) extraction from nitric acid solution with 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone as a cation carrier by liquid membrane emulsion
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Copper(II) extraction from nitric acid solution with 1-phenyl-3-methyl-4-benzoil-5-pyrazolone (HPMBP) as a cation carrier by liquid membrane emulsion (LME) was investigated. The HPMBP initially was synthesized and the synthesis yield is a yellow crystal with melting point of 87-89 °C. The synthesis efficiency is 72.04% and generally the spectra of IR, 1H NMR and 13C NMR agree with HPMBP structure. The optimum condition for copper(II) extraction were found as follows: concentration of mixed surfactant (span 80+span 20) was 3%, volume ratio of membrane and internal phase was 1, concentration of HPMBP was 0.020 M, concentration of HCl was 1 M, volume ratio of emulsion and external phase was 0.143. By using these optimum conditions, 30 mL of LME can extract 1000 ppm of copper(II) within 210 mL of nitric acid solution with extraction percentage of 97.97%.
- Hamzah, Baharuddin,Jalaluddin, Noor,Wahab, Abdul Wahid,Upe, Ambo
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- Isolation, characterization and X-ray structure determination of the Schiff base ligand: 5-methyl-2-phenyl-4-[phenyl-(4-phenyl-thiazol-2-ylamino)-methylene]-2,4-dihydro-pyrazol-3-one
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The structure of the amine tautomer of the new Schiff base derived from 4-benzoyl-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one (2) and 4-phenyl-thiazol-2-ylamine (3) was confirmed by means of single crystal X-ray diffraction. The title compound (4) was synthesized and crystals were grown from a mixture of dichloromethane and n-hexane (1:3). Single crystal X-ray diffraction analysis show that the structure is primarily stabilized by strong intramolecular N3-H3A...O1 hydrogen bonds [N3-H3A = 0.883(19) ?, H3A...O1=1.925(18) ?, N3...O1=2.6901(13) ?, with an angle for N3-H3A...O1=144.1(17) °] and this leads to the formation of a pseudo nine-membered hydrogen bonded pattern. Elemental analysis, FTIR andNMRanalyses have been employed to characterize the crystal.
- Thakar, Amit S.,Friedrich, Holger B.,Joshi, Krishnalal T.,Maguire, Glenn E.M.
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- Introduction of new ancillary ligands to the iridium complexes having 2,3-diphenylquinolinato ligands for OLED
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We investigated the effect of an ancillary ligand (AL) on the emission color and luminous efficiencies of its complex, Ir(4-Me-2,3-dpq)2(AL), where 4-Me-2,3-dpq represents 4-methyl-2,3-diphenylquinolinato ligand. We expected that ancillary ligand modification by introduction of the bulky substituent to the complexes might allow luminous efficiency increase by reduction of T-T annihilation. Furthermore, some ancillary ligands may contribute to fine-tuning of their complex emission colors by influencing the energy level of Ir d-orbitals upon the orbital mixing. As new ancillary ligands substituting for acac which is a typical AL in the iridium complexes, pyrazolone-based ligands, 4-R-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one series (przl-R), were prepared, where R represents C6H5, C6H4CH3 and C6H4Cl. These ligands were chelated to the iridium center to yield a new series of the iridium complexes, Ir(4-Me-2,3-dpq)2(przl-R). The X-ray crystal structure of Ir(4-Me-2,3-dpq)2(przl-C6H4Cl) was determined. The electrochemical and luminescence properties of the iridium complexes were investigated. The effect of the przl-substituents on the emission colors of the complexes was not significant. On the other hand, the luminous efficiencies of Ir(4-Me-2,3-dpq)2(przl-C6H5) and Ir(4-Me-2,3-dpq)2(przl-C6H4CH3) were higher than that of Ir(4-Me-2,3-dpq)2(acac).
- Lee, Hyun Shin,Ahn, So Youn,Huh, Hyun Sue,Ha, Yunkyoung
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- Synthesis and the luminescent study of the iridium complexes containing 2,3-diphenylquinoline derivatives and the new ancillary ligand for OLED
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We previously reported that Ir(6-F-2,3-dpqx-(OMe)2) 2(acac) (6-F-2,3-dpqx-(OMe)2=6-fluoro-2,3-bis(4- methoxylphenyl)quinoxaline) exhibited photoluminescence(PL) and electroluminescence (EL) emission at 645 and 667nm, respectively. To modulate the emission maxima toward the saturated red chromacity, a new main ligand and its iridium complexes were prepared, and their photophysical properties were investigated. As a main ligand, 6-OMe-2,3-dpqx-(OMe)2 (6-OMe-2,3-dpqx-(OMe)2=6-methoxy-2,3-bis(4-methoxylphenyl) quinoxaline), were designed and synthesized. Acetylacetonate (acac) and pyrazolonates (przls) were also chelated to the iridium center as an ancillary ligand. The resulting complexes prepared herein were Ir(6-OMe-2,3-dpqx-(OMe) 2)2(acac), Ir(6-OMe-2,3-dpqx-(OMe)2) 2(przl1) and Ir(6-OMe-2,3-dpqx-(OMe)2)2(przl2). The photoluminescence (PL) of these complexes were observed around 660nm, and their electroluminescence maxima were observed around 650nm. The PL investigation of the complexes in PMMA (PMMA=poly(methylmetacrylate)) for the polymer solution process revealed that the emission peaks became broader with the range of 600~850nm than those of the complexes only.
- Lee, Hyun-Shin,Ahn, So Youn,Ha, Yunkyoung
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experimental part
p. 14 - 24
(2010/07/14)
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- New series of antiprion compounds: Pyrazolone derivatives have the potent activity of inhibiting protease-resistant prion protein accumulation
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To find effective antiprion compounds, we synthesized and evaluated various pyrazolone derivatives. Seven of 19 compounds showed inhibition of PrP-res accumulation and the remarkably active compound 13 showed an IC50 value of 3 nM in both ScN2a and F3 cell lines. Findings from studies on physicochemical and biochemical properties suggest that the action mechanism of these compounds does not correlate with any antioxidant activities, any of hydroxyl radical scavenging activities, or any SOD-like activities.
- Kimata, Ayako,Nakagawa, Hidehiko,Ohyama, Ryo,Fukuuchi, Tomoko,Ohta, Shigeru,Suzuki, Takayoshi,Miyata, Naoki
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p. 5053 - 5056
(2008/03/13)
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- Neutral dioxovanadium(V) complexes of biomimetic hydrazones ONO donor ligands of bioinorganic and medicinal relevance: Synthesis via air oxidation of bis(acetylaceto-nato)oxovanadium(IV), characterization, biological activity and 3D molecular modeling
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The interaction of bis(acetylacetonato)oxovanadium(IV), [VO(acac)2] with biomimetic hydrazone ONO donor ligands HL in 1:1 mole ratio [where, HL = N-(4′-benzoylidene-3′-methyl-1′-phenyl-2′-pyrazolin-5′-one)-isonicotinic acid hydrazide (bmphp-inH, I), N-(4′-butyrylidene-3′-methyl-1′-phenyl-2′-pyrazolin-5′-one)-isonicotinic acid hydrazide (bumphp-inH, II), N-(4′-acetylidene-3′-methyl-1′-phenyl-2′-pyrazolin-5′-one)-isonicotinic acid hydrazide (amphp-inH, III), N-(3′-methyl-1′-phenyl-4′-propionylidene-2′-pyrazolin-5′-one)-isonicotinic acid hydrazide (mphpp-inH, IV) and N-(4′-iso-butyrylidene-3′-methyl-1′-phenyl-2′-pyrazolin-5′-one)-isonicotinic acid hydrazide (iso-bumphp-inH, V)] in a mixed solvent (ethanol-methanol, 1:10) via aerial oxidation for 2-3 days yield dioxovanadium(V) complexes of composition [VO2(L)(H2O)] · H2O. The compounds so obtained were characterized on the basis of elemental analyses, thermogravimetry, vanadium determination, IR, Electronic, 51V NMR, 1H NMR and mass spectral studies. The 3D molecular modeling and analysis for bond lengths and bond angles have also been carried out for one of the representative compounds, [VO2(ampph-in)(H2O)] (3).
- Maurya,Rajput
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p. 133 - 144
(2008/10/09)
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- Metal nitrosyl complexes of bioinorganic, catalytic, and environmental relevance: A novel single-step synthesis of dinitrosylmolybdenum(0) complexes of {Mo(NO)2}6 electron configuration involving Schiff bases derived from 4-acyl-3-methyl-1-phenyl-2-pyrazolin-5-one and 4-aminoantipyrine, directly from molybdate(VI) and their characterization
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This paper reports the synthesis of five new hexa-coordinated mixed-ligand dinitrosyl complexes of molybdenum(0) of the composition [Mo(NO)2(L)(OH)], where LH = N-(3′-methyl-1′-phenyl-4′-valerylidene-2′-pyrazolin-5′-one)-4-aminoantipyrine (mphvp-aapH), N-(4′-benzoylidene-3′-methyl-1′-phenyl-2 ′-pyrazolin-5′-one)-4-aminoantipyrine (bmphp-aapH), N-(3′-methyl-1′-phenyl-4′-propionylidene-2′-pyrazolin-5′-one)-4-aminoantipyrine (mphpp-aapH), N-(4′-acetylidene-3′-methyl-1′-phenyl-2′-pyrazolin-5 ′-one)-4-aminoantipyrine (amphp-aapH) or N-(-4′-iso-butyrylidene-3′-methyl-1′-phenyl-2′-pyrazolin-5′-one)-4-aminoantipyrine (iso-bumphp-aapH) directly from molybdate (VI) in a single step and in a single pot. The compounds so obtained have been characterized by elemental analyses, molar conductance, decomposition temperature and magnetic measurements, thermogravimetric analyses, infrared and electronic spectral studies. They were found to contain low-spin [Mo(NO)2]6 electron configuration. A cis-octahedral structure has been proposed for these complexes. The 3D molecular modeling and analysis for bond lengths and bond angles have also been carried out for one of the representative compounds, [Mo(NO)2(bmphp-aap)(OH)] (2).
- Maurya,Pandey,Chaurasia,Martin
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- Hydroxyl radical scavenging by edaravone derivatives: Efficient scavenging by 3-methyl-1-(pyridin-2-yl)-5-pyrazolone with an intramolecular base
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We synthesized various 3-methyl-1-phenyl-5-pyrazolone (edaravone) derivatives and evaluated their oxidation potential and hydroxyl radical scavenging activity. It was found 3-methyl-1-(pyridin-2-yl)-5-pyrazolone had a much higher ability to scavenge the radical than did edaravone itself. Its efficient radical scavenging activity was assumed to be due to the increase of its anion form, an active form, by a hydrogen-bonded intramolecular base.
- Nakagawa, Hidehiko,Ohyama, Ryo,Kimata, Ayako,Suzuki, Takayoshi,Miyata, Naoki
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p. 5939 - 5942
(2007/10/03)
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- Gravimetric Determination of Uranium(VI) and Thorium(IV) with Substituted Pyrazolones
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4-Acylpyrazolones like 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (PMPB), 1-phenyl-3-methyl-4-p-nitrobenzoyl-5-pyrazolone (PMNP) and 1-phenyl-3-methyl-4-(3,5-dinitrobenzoyl)-5-pyrazolone (PMDP) have been synthesized and developed as gravimetric reagents for the determination of U(VI) and Th(IV).Uranium(VI) is almost quantitatively precipitated with PMBP, PMNP and PMDP at pH 2.20, 1.85 and 1.70 respectively.The pH values for the complete precipitation of thorium(IV) with PMBP, PMNP and PMDP are 2.90, 2.75 and 2.50 respectively.PMBP has proved to be an efficient ligand for gravimetric determination of U(VI) by direct weighing method after drying at 100 +/- 10 deg C.The percentage relative error varies from 0.4 to 1.6 in the determination of U(VI) by this method.The effect of a number of interfering ions on the precipitation of U(VI) by PMBP has been reported.
- Arora, H. C.,Rao, G. N.
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p. 539 - 540
(2007/10/02)
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