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Journal articles on the topic 'Pyrazoline one-5(benzoyl-4 methyl-3 phenyl-1)'

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Published: 4 June 2021

Last updated: 17 February 2022

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1

Lesnov, Andrey E., Peter T. Pavlov, Larisa V. Pustovik, and Irina А. Sarana. "1-ALKYL-3-METHYL-4-HYDROXYIMINO-2-PYRAZOLINE-5-ONES AS EXTRACTION REAGENTS." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 60, no. 5 (June 23, 2017): 30. http://dx.doi.org/10.6060/tcct.2017605.5527.

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With nitrosation of the corresponding 1-R-3-methylpyrazole-5-one (R = C4H9, C5H11, C6H13, C7H15, C8H17, C6H5) in acidic aqueous methanolic medium at 0-5 °C a series of 1-alkyl-3-methyl-4-hydroxyimino-2-pyrazolin-5-ones with a yield of 72-85% were synthesized. The compounds are soluble in CHCl3, C2H4Cl2, C6H5CH3, i-C4H9OH, CCl4, C2H5OH, slightly soluble in C6H14, H2O. They can be recrystallized from a mixture of C6H14: C6H5CH3 = 5: 1 or isooctane. The structure of the compounds was confirmed by the data of ECR, IR, Raman spectroscopy and TLC data. The interphase distribution of oxyiminopyrazolones between chloroform and aqueous solutions was studied as a function of pH. In alkaline media, the reagents completely transferred into the aqueous phase. In acidic solutions, up to 1 mol/l HCl, the compounds are in the organic phase. The maximum values of the partition coefficient are observed for the reagents with the maximum length of the aliphatic radical. The effect of the length of aliphatic radical at the first position of the pyrazoline ring on their extraction properties were studied by example of extraction of nickel and copper (II) ions. The length of the radical does not affect the composition of the recoverable complexes of nickel and copper (II). In all cases the ratio is close to 1:2. Extraction proceeds through a cation-exchange mechanism. Replacement of the phenyl radical in the first position of the pyrazoline ring by an aliphatic resulted to the increase in partition constants of the reagents between chloroform and aqueous solutions. The range of pH values of the maximum extraction of elements was widened. The capacity of the extractant for metals also increased. At the same time, the pH50 extraction values remained practically unchanged. In the case of 0.05 mol/l solution of 1-phenyl-3-methyl-4-oxyimino-2-pyrazolin-5-one in chloroform, when the extract was saturated with the metal ion, precipitation of the complex was observed.For citation:Lesnov A.E., Pavlov P.T., Pustovik L.V., Sarana I.A. 1-Alkyl-3-methyl-4-hydroxyimino-2-pyrazoline-5-ones as extraction reagents. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 5. P. 30-36.

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2

Mistry, Rakesh N., and K. R. Desai. "Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione,para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity." E-Journal of Chemistry 2, no. 1 (2005): 30–41. http://dx.doi.org/10.1155/2005/953107.

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1, 2 - Dichloro benzene on chlorosulphonation by chlorosulphonic acid gives 1, 2 - [dichloro] - benzene sulphonyl chloride which on condensation withp–amino acetophenone gives 1-[acetyl] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative. This derivative undergo condensation with 2,4- dichloro benzaldehyde gives 1- [3” - (sub. phenyl) - 2” - propene - 1” - one] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative which on reaction with 99% hydrazine hydrate and glacial acetic acid gives 1-[acetyl]-3- [1’ , 2’ - (dichloro) - dibenz sulphonamide] -5 - [2” , 4” - dichloro phenyl] - 2 - pyrazoline derivative. This derivative reacts with various substituted aldehydes to give corresponding substituted chalcone derivatives [1(a-j)]. Now, these chalcone derivatives [1(a-j)] on condensation with urea gives corresponding substituted pyrimidine - 2 - one derivatives [2(a-j)] and on condensation with thio-urea gives corresponding substituted pyrimidine- 2 -thione derivatives [3(a-j)]. Further, these chalcone derivatives [1(a-j)] on reaction with 99% hydrazine hydrate gives 1 - [1’ - (H) - 5’ - (sub. phenyl) - 2’ - pyrazoline]- 3 - [1” , 2” - (dichloro) - dibenz sulphonamide] - 5 - [2’’’ , 4’’’ - dichloro phenyl]-2- pyrazoline derivatives [4(a-j)] as an intermediate compounds, which on condensation with p-acetanilide sulphonyl chloride gives corresponding substituted p - acetanilide sulphonyl derivatives [5(a-j)] and on condensation with benzoyl chloride gives corresponding substituted benzoyl derivatives [6(a-j)]. Structure elucidation of synthesised compounds has been made on the basis of elemental analysis, I.R. spectral studies and 1H N.M.R. spectral studies. The antimicrobial activity of the synthesised compounds has been studied against the cultures “Staphylococcus aureus”, “Escherichia coli” and “Candela albicans”.

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3

K, Ishwar Bhat, and Abhishek Kumar. "PYRAZOLINES AS POTENT ANTITUBERCULAR AND CYTOTOXIC AGENTS." Asian Journal of Pharmaceutical and Clinical Research 10, no. 6 (June 1, 2017): 247. http://dx.doi.org/10.22159/ajpcr.2017.v10i6.17344.

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Objective: Pyrazolines are known to exhibit different biological and pharmacological properties such as anticancer, antibacterial, antifungal and antitubercular activities. Chalcones with an enone group between two aromatic rings exhibit remarkable pharmacological activities such as antiinflammatory, antibacterial, antitumor, antifungal, and antimalarial activity. A series of pyrazolines from chalcones have been synthesized and evaluated for antitubercular and cytotoxic activity studies.Methods: Chalcones [3-substituted phenyl-1-(p-tolyl)prop-2-en-1-one] were synthesized from various substituted aldehydes and 4-methyl acetophenone and cyclized into pyrazolines [5-substituted phenyl-3-(p-tolyl)-4,5-dihydro-1H-pyrazole] using hydrazine hydrate. Antitubercular and cytotoxic activity studies were carried out.Results: Antitubercular and cytotoxic activity studies of synthesized pyrazoline revealed that some compounds have showed promising activity.Conclusion: The observed results proved that pyrazolines are found to be interesting lead molecules for further synthesis as antitubercular and cytotoxic agents.

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4

Idemudia, Omoruyi G., Alexander P. Sadimenko, and Eric C. Hosten. "Crystal structure of 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one sulfadiazine dimethylformamide monosolvate, C30H29N7O4S." Zeitschrift für Kristallographie - New Crystal Structures 229, no. 4 (December 1, 2014): 455–57. http://dx.doi.org/10.1515/ncrs-2014-0216.

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5

Ahmadia, F., A. Khanmohammadi, and A. Malekpour. "MICELLE-MEDIATED EXTRACTION AS A TOOL FOR SEPARATION AND PRECONCENTRATION IN COPPER ANALYSIS." Indonesian Journal of Chemistry 7, no. 3 (June 20, 2010): 278–83. http://dx.doi.org/10.22146/ijc.21669.

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A cloud point extraction method was presented for preconcentration of copper in various samples. After complexation with 4-Amino-2,3-dimethyl-1-phenyl-3-pyrazoline-5-one (ADPP) or N-Benzoyl-N-phenylhydroxylamine (BPA) in water, analyte ions are quantitatively extracted to the phase rich in Triton X-114 after centrifugation. 2.0 mol L-1 HNO3 solution in methanol was added to the surfactant-rich phase prior to its analysis by flame atomic absorption spectrometry (FAAS). The adopted concentrations for ADPP, Triton X-114, HNO3 and parameters such as bath temperature, centrifuge rate and time were optimized. Detection limits (3SDb/m) of 1.3 and 1.9 ng mL-1 for ADPP and BPA along with enrichment factors of 30 and 38 for ADPP and BPA were achieved. The high efficiency of cloud point extraction to carry out the determination of analyte in complex matrices was demonstrated. The proposed method was applied to the analysis of biological, industrial, natural and wastewater, soil and blood samples. Keywords: 4-Amino-2,3-dimethyl-1-phenyl-3-pyrazoline-5-one (ADPP), N-Benzoyl-N-phenylhydroxylamine (BPA) , Cloud Point Extraction, Triton X-114, Flame Atomic Absorption Spectrometry.

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6

Lesnov, Andrey E., Larisa V. Pustovik, and Irina A. Sarana. "EXTRACTION OF METAL IONS BY 4-BENZOYL- OR 4-(3-NYTROBENZOYL-1-HEXYL- 3-METHYL-2-PYRAZOLINE-5-ONES." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 63, no. 9 (August 5, 2020): 63–69. http://dx.doi.org/10.6060/ivkkt.20206309.6216.

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The extraction properties of solutions of 4-benzoyl- and 4- (3-nitrobenzoyl) -1-hexyl-3-methyl-2-pyrazolin-5-ones in chloroform were studied. The pH dependence of the degree of extraction is S-shaped. Ions Cu2+, Pb2+, Zn2+, Ni2+, Co2+, Mn2+, Cd2+, Ca2+, Mg2+ are extracted in the form of complexes with the ratio M (II): reagent determined by the equilibrium shift method equals to 1: 2. A lower equilibrium pH than the initial value indicates a cation-exchange extraction mechanism. The introduction of an electronegative nitro group into the benzoyl fragment of the reagent led to a shift in the pH50 values of the extraction of metal ions in a more acidic region. The presence of a correlation between the values of the Klopman hardness parameters of the above metal cations and extraction pH50 values was shown. The influence of the nature of the solvent on the extraction of zinc ions was studied. The addition of polar isopentanol to the extractant shifts the pH of the metal extraction to a more acidic region. In order to increase the pH50 value of zinc extraction, the solvents are arranged in a row: 30% isopentanol in CHCl3 < benzene < xylene < toluene < chloroform < dichloroethane. The introduction of additional neutral electron-donating hydrophobic organic compounds into the extract: 1-hexyl-3-methyl-2-pyrazolin-5-one, triisobutyl phosphate, trioctylphosphine oxide significantly increases the values of the partition coefficients of zinc. The observed synergistic effect is explained by the formation of a coordinatively unsaturated intracomplex compound of zinc with aroylpyrazolone, in which the free coordination sites are filled with neutral reagent molecules. In this case, water is replaced and due to the increased hydrophobicity of the complex, an increase in extraction occurs. Confirmation of the formation of a coordination-unsaturated zinc complex is a close to unity value of the slope of the decimal logarithm of the metal distribution constant for pH.

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7

Sock, Sung Yun, Beom Yang Han, and Park Hyun-Soo. "The thermodynamics of synergistic solvent extraction of Zn(II) with 1-phenyl-3- methyl-4-benzoyl-pyrazole-5-one." Polyhedron 4, no. 11 (January 1985): 1865–68. http://dx.doi.org/10.1016/s0277-5387(00)86702-9.

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8

Idemudia, Omoruyi G., and Eric C. Hosten. "Bis(4-benzoyl-3-methyl-1-phenyl-1H-pyrazol-5-olato-κ2O,O′)bis(ethanol-κO)cobalt(II)." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (July 25, 2012): m1107—m1108. http://dx.doi.org/10.1107/s1600536812032837.

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The title compound, [Co(C17H13N2O2)2(C2H5OH)2], is a CoIIcomplex with two 4-benzoyl-3-methyl-1-phenyl-1H-pyrazol-5-olate (BMPP) ligands and two coordinating ethanol molecules. In the asymmetric unit, there are two half molecules, with the CoIIatoms located on inversion centres. The two cobalt complexes have slightly different geometries and in one, the ethyl group of the ethanol is disordered over two sets of sites [occupancy ratio 0.757 (7):0.243 (7)]. Each BMPP ligand is deprotonated with the negative charge delocalized. The hydroxy group of each ethanol molecule forms hydrogen bonds with a pyrazole N atom in an adjacent BMPP ligand. Weaker C—H...O and C—H...N interactions link the molecules into a three-dimensional structure.

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9

Maurya, R. C., P. K. Vishwakarma, J. M. Mir, and D. K. Rajak. "Oxidoperoxidomolybdenum(VI) complexes involving 4-formyl-3-methyl-1-phenyl-2-pyrazoline-5-one and some β-diketoenolates." Journal of Thermal Analysis and Calorimetry 124, no. 1 (January 30, 2016): 57–70. http://dx.doi.org/10.1007/s10973-015-5234-4.

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10

METWALLY, S. A. M., G. M. EL-NAGGAR, and T. I. EL EMARY. "ChemInform Abstract: Reactions of 4-(Dicyanomethylene)-3-methyl-1-phenyl-2-pyrazoline-5-one Towards Active Methylene Compounds." ChemInform 22, no. 48 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199148063.

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11

Zong, Ziao, Xiaodan Wei, Xingchen Yan, and Yuhua Fan. "Crystal structures and anticancer activities of five novel pyrazolone-enamine transition metal complexes with 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one." Journal of Molecular Structure 1171 (November 2018): 333–39. http://dx.doi.org/10.1016/j.molstruc.2018.06.019.

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12

Yan, Xingchen, Xiaojing Wu, Jiakun Xu, Yuhua Fan, Caifeng Bi, Xia Zhang, and Zhongyu Zhang. "Crystal structures and theoretical calculations of two peculiar compounds derived from 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one." Journal of Molecular Structure 1074 (September 2014): 609–16. http://dx.doi.org/10.1016/j.molstruc.2014.06.057.

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13

Idemudia, Omoruyi, Alexander Sadimenko, and Eric Hosten. "Metal Complexes of New Bioactive Pyrazolone Phenylhydrazones; Crystal Structure of 4-Acetyl-3-methyl-1-phenyl-2-pyrazoline-5-one phenylhydrazone Ampp-Ph." International Journal of Molecular Sciences 17, no. 5 (May 18, 2016): 687. http://dx.doi.org/10.3390/ijms17050687.

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14

Liu, Chong-Bo, Yuan Chen, Liu-Shui Yan, De-He Huang, and Zhi-Qiang Xiong. "Syntheses, Characterization, and Antibacterial Activities of Four New Schiff Base Compounds Derived from 1-Phenyl-3-methyl-4-benzoyl-2-pyrazolin-5-one." Journal of Heterocyclic Chemistry 49, no. 4 (July 2012): 839–44. http://dx.doi.org/10.1002/jhet.874.

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15

El-Sawaf, Ayman K. "Synthesis, Magnetic, Spectral and Biological Studies of Copper(II) Complexes of 4-Benzoyl-3-Methyl-1-Phenyl-2-Pyrazolin-5-One N(4)-Substituted Thiosemicarbazones." Science Journal of Chemistry 2, no. 3 (2014): 17. http://dx.doi.org/10.11648/j.sjc.20140203.12.

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16

Idemudia, Omoruyi G., Alexander P. Sadimenko, and Anthony J. Afolayan. "Potential therapeutic Mn2+and Ni2+complexes of new 4-acetyl-3-methyl-1-phenyl-2-pyrazoline-5-one phenylhydrazone Ampp-Ph." Macromolecular Symposia 351, no. 1 (May 2015): 61–68. http://dx.doi.org/10.1002/masy.201300128.

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17

Atanassova, Maria, and Ivan L. Dukov. "Synergistic solvent extraction and separation of trivalent lanthanide metals with mixtures of 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one and aliquat 336." Separation and Purification Technology 40, no. 2 (December 2004): 171–76. http://dx.doi.org/10.1016/j.seppur.2004.02.007.

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18

Awad, Ibrahim M. A. "Studies in the Vilsmeier-Haack reaction, part VII: Synthesis and reaction of 3-methyl-1-phenyl-4-acetyl hydrazono 2-pyrazoline-5-one(-5-thione)." Monatshefte f�r Chemie Chemical Monthly 121, no. 12 (December 1990): 1023–30. http://dx.doi.org/10.1007/bf00809252.

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19

Metwally, Saoud A. M., Moustafa F. Aly, Mohamed A. Abd-Alla, Ferial M. Atta, and Maisa E. Abd-El-Monem. "Azomethine ylides from the reaction of 4-(dicyanomethylene)-3-methyl-1-phenyl-2-pyrazoline-5-one with α-amino acids and their esters." Liebigs Annalen der Chemie 1991, no. 4 (April 12, 1991): 387–89. http://dx.doi.org/10.1002/jlac.199119910168.

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20

Idemudia, Omoruyi G., Alexander P. Sadimenko, Anthony J. Afolayan, and Eric C. Hosten. "Synthesis and Characterization of Bioactive Acylpyrazolone Sulfanilamides and Their Transition Metal Complexes: Single Crystal Structure of 4-Benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one Sulfanilamide." Bioinorganic Chemistry and Applications 2015 (2015): 1–14. http://dx.doi.org/10.1155/2015/717089.

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Two Schiff base ligands Ampp-Sn1and Bmpp-Sn2, afforded by a condensation reaction between sulfanilamide and the respective acylpyrazolone carbonyl precursors, their Mn(II), Co(II), Ni(II), and Cu(II) complexes prepared by the reaction of ligands and corresponding metal salts in aqueous solutions, were synthesized and then characterized by both analytical and spectroscopic methods, in a view to developing new improved bioactive materials with novel properties. On the basis of elemental analysis, spectroscopic and TGA results, transition metal complexes, with octahedral geometry having two molecules of the bidentate keto-imine ligand each, have been proposed. The single crystal structure of Bmpp-Sn according to X-ray crystallography showed a keto-imine tautomer type of Schiff base, having three intramolecular bonds, one short N2⋯H2⋯O3 hydrogen bond of 1.90 Å and two long C13⋯H13⋯O2 and C32⋯H32⋯O3 hydrogen bonds of 2.48 Å. A moderate to low biological activities have been exhibited by synthesized compounds when compared with standard antimicrobial agents on screening the synthesized compounds againstStaphylococcus aureus,Bacillus pumilus,Proteus vulgaris, andAeromonas hydrophilafor antibacterial activity and against free radical 1, 1-diphenyl-2-picryl-hydrazyl (DPPH) for antioxidant activity.

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21

Maurya, R. C., D. D. Mishra, N. Sumita Rao, and N. Nageswara Rao. "Synthesis and Characterization of Novel Ruthenium(II) Chelates with Some Schiff Bases Derived from 4-Benzoyl-3-Methyl-1-Phenyl-2-Pyrazolin-5-One and Sulpha Drugs." Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 24, no. 6 (July 1994): 1013–25. http://dx.doi.org/10.1080/00945719408001318.

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22

AWAD, I. M. A. "ChemInform Abstract: Studies in the Vilsmeier-Haack Reaction. Part 7. Synthesis and Reaction of 3-Methyl-1-phenyl-4-acetyl Hydrazono 2-Pyrazoline-5-one(-5- thione)." ChemInform 22, no. 15 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199115165.

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23

Kiran, Kothuri, Dongamanti Ashok, Boddu Rao, Madderla Sarasija, and Alapati Rao. "Synthesis of novel pyrazoline based bis (1,2,3-triazole) scaffolds via click chemistry." Journal of the Serbian Chemical Society 82, no. 3 (2017): 241–51. http://dx.doi.org/10.2298/jsc160216076a.

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A series of novel bis(1,2,3-triazoles) derivatives 7a?m were synthesized by the 1,3-dipolar cycloaddition (click-reaction) of 1-methyl-3,5-bis(2- -(prop-2-yn-1-yloxy)phenyl)-4,5-dihydro-1H-pyrazole (5) with various aralkyl azides 6a?m in the presence of sodium ascorbate and copper sulphate with good yields. The required precursor 5 was synthesized by reacting (E)-1,3- -bis(2-hydroxyphenyl)prop-2-en-1-one (3) with methylhydrazine hydrate via 2,2?-(1-methyl-4,5-dihydro-1H-pyrazole-3,5-diyl)diphenol 4, followed by reaction with propargyl bromide. The homogeneity of all the newly synthesized compounds was checked by TLC. The IR, NMR, mass spectral data and elemental analysis were in accord with the assigned structure. The title compounds were evaluated for their antibacterial activity against various bacterial strains, i.e., Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis; compounds 7f?7h and 7j were found to be moderately active against the bacteria, when compared with that of the standard drug. Furthermore, the same library of compounds was evaluated for their antioxidant activity using the nitric oxide radical scavenging activity. The results of the study showed that compounds 7e?7h and 7k?7m showed good radical scavenging activity.

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24

METWALLY, S. A. M., M. F. ALY, M. A. ABD-ALLA, F. M. ATTA, and M. E. ABD-EL-MONEM. "ChemInform Abstract: Azomethine Ylides from the Reaction of 4-(Dicyanomethylene)-3-methyl-1- phenyl-2-pyrazoline-5-one with α-Amino Acids and Their Esters." ChemInform 22, no. 32 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199132157.

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25

Atanassova, Maria, and Ivan Dukov. "A Comparative Study of the Solvent Extraction of the Trivalent Elements of the Lanthanoid Series with Thenoyltrifluoroacetone and 4-Benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one Using Diphenylsulphoxide as Synergistic Agent." Journal of Solution Chemistry 38, no. 3 (January 30, 2009): 289–301. http://dx.doi.org/10.1007/s10953-009-9374-7.

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26

Uhlemann, Erhard, Uwe Schilde, and Frank Weller. "Calcium- und Bariumkomplexe mit 1-Phenyl-3-methyl-4-benzoylpyrazol-5-on / Calcium and Barium Complexes with 1-Phenyl-3-methyl-4-benzoyl-5-pyrazolone." Zeitschrift für Naturforschung B 50, no. 1 (January 1, 1995): 31–36. http://dx.doi.org/10.1515/znb-1995-0106.

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The calcium and barium complexes with 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone have been synthesized and characterized by X-ray structural analysis. Besides two molecules of the ligand, the calcium atom binds two molecules of ethanol in an octahedral coordination. The barium atom attains the coordination number 8 by coordinating 4 molecules of the pyrazolone ligand.

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27

Di Nicola, Corrado, Fabio Marchetti, Riccardo Pettinari, Alessia Tombesi, Claudio Pettinari, Iolanda Grappasonni, Paul J. Dyson, and Stefania Scuri. "Tethering (Arene)Ru(II) Acylpyrazolones Decorated with Long Aliphatic Chains to Polystyrene Surfaces Provides Potent Antibacterial Plastics." Materials 13, no. 3 (January 22, 2020): 526. http://dx.doi.org/10.3390/ma13030526.

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The acylpyrazolone proligands HQR (HQR in general, in detail: HQCy = 1-phenyl-3-methyl-4-carbonylcyclohexyl-5-pyrazolone, 4-C(O)-phenyl, HQPh = 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone, HQC17 = 1-phenyl-3-methyl-4-stearoyl-5-pyrazolone, HQC17,Ph = 1-phenyl-3-stearyl-4-benzoyl-5-pyrazolone) were synthesized and reacted with (arene)Ru(II) acceptors affording complexes [(arene)Ru(QR)Cl] (arene = cymene (cym) or hexamethylbenzene (hmb)). The complexes were characterized by elemental analyses, thermogravimetric analysis-Differntial Thermal Analysis (TGA-DTA), IR spectroscopy, ESI-MS and 1H, and 13C NMR spectroscopy. Complexes [(arene)Ru(QR)Cl] where QR = QC17 and QC17,Ph, due to the long aliphatic chain in the ligand, afford nanometric dispersions in methanol via self-assembly into micellar aggregates of dimensions 50–200 nm. The antibacterial activity of the complexes was established against Escherichia coli and Staphylococcus aureus, those containing the ligands with a long aliphatic chain being the most effective. The complexes were immobilized on polystyrene by a simple procedure, and the resulting composite materials showed to be very effective against E. coli and S. aureus.

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28

Uhlemann, Erhard, Alwin Friedrich, Gerald Hinsche, Wulfhard Mickler, and Uwe Schilde. "Komplexbildung und Metallextraktion mit heterocyclischen β-Dicarbonylverbindungen im Vergleich. Struktur von 3-Phenyl-4-benzoyl-isoxazol-5-on / Complex Formation and Metal Extraction with Heterocyclic β-Dicarbonyl Compounds as Comparison. Structure of 3-Phenyl-4-benzoyl-5-isoxazolone." Zeitschrift für Naturforschung B 50, no. 1 (January 1, 1995): 37–42. http://dx.doi.org/10.1515/znb-1995-0107.

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Acid constants and stability constants of nickel and zinc chelates with 2-thenoyltrifluoroacetone, dibenzoylmethane, 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone and 3-phenyl-4-benzoyl-5-isoxazolone were compared. The extraction of copper was studied. Thermoanalytic measurements were made using the ligands and their copper compounds in the solid state. The molecular structure of 3-phenyl-4-benzoyl-5-isoxazolone was determined by X-ray analysis. Crystal data: a = 874,7(2), b = 1959,2(7), c = 897,38(7) pm; β = 101,030(7)°; space group P 121/c 1; Z = 4; R = 0,043; 1920 observed, unique reflexions.

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29

Maurya, R. C., H. Singh, and A. Pandey. "OXOVANADIUM(IV) COMPLEXES OF BIOINORGANIC AND INDUSTRIAL RELEVANCE: SYNTHESIS AND CHARACTERIZATION OF SOME OXOVANADIUM(IV) COMPLEXES INVOLVING SCHIFF BASES DERIVED FROM BIOLOGICALLY ACTIVE 4-BENZOYL-3-METHYL-1-PHENYL-2-PYRAZOLIN-5-ONE AND CERTAIN AROMATIC AMINES." Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 32, no. 2 (September 4, 2002): 231–46. http://dx.doi.org/10.1081/sim-120003205.

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30

Jasril, Jasril, Neni Frimayanti, Yuana Nurulita, Adel Zamri, Ihsan Ikhtiarudin, and Guntur Guntur. "5-(4-Fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole." Molbank 2021, no. 1 (March 10, 2021): M1197. http://dx.doi.org/10.3390/m1197.

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A new fluorinated pyrazole, 5-(4-fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole was successfully synthesized via a two-step reaction. Firstly, the synthesis of pyrazoline was performed via one-pot three-component reaction under microwave irradiation. Secondly, the synthesis of pyrazole was performed via oxidative aromatization of pyrazoline under conventional heating. The structure of the synthesized compound was confirmed by spectroscopic analysis, including FT-IR, HR-MS, 1D and 2D NMR analysis. Then, molecular docking study showed that the binding affinity of the synthesized compound to human estrogen alpha receptor (ERα) was close to 4-OHT as a native ligand.

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31

AKAMA, Yoshifumi, Mituharu SANBE, Motoo SHIRO, Naohisa MATSUMOTO, Kenji SATO, and Hitoshi KANNO. "Thermal properties of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone." Bunseki kagaku 44, no. 1 (1995): 25–28. http://dx.doi.org/10.2116/bunsekikagaku.44.25.

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32

Jasril, Jasril, Hilwan Yuda Teruna, Aisyah Aisyah, Nurlaili Nurlaili, and Rudi Hendra. "Microwave Assisted Synthesis and Evaluation of Toxicity and Antioxidant Activity of Pyrazoline Derivatives." Indonesian Journal of Chemistry 19, no. 3 (May 29, 2019): 583. http://dx.doi.org/10.22146/ijc.34285.

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Four pyrazoline analogues, 3-(4-methoxyphenyl)-5-naphthalene-1-yl-1-phenyl-4,5-dihydro-pyrazole (3), 3-(4-methoxyphenyl)-5-naphthalene-1-yl-4,5-dihydro-1H-pyrazole (4), 3-(2-methoxyphenyl)-5-naphthalene-1-yl-1-phenyl-4,5-dihydro-pyrazole (5) and 3-(2-methoxyphenyl)-5-naphthalene-1-yl-4,5-dihydro-1H-pyrazole (6) were synthesized via intermolecular cyclization between substituted chalcones and hydrazine derivatives. The compounds were synthesized in two steps. In the first step, the chalcones were synthesized by Claisen-Schmidt reaction. In the second step, they were cyclized with some hydrazine derivatives to form pyrazolines by using glacial acetic acid as a catalyst and assisted by microwave irradiation. The toxicity analysis showed that compound 1 and 2 were toxic with LC50 values of 11.47 and 0.97 μg/mL, respectively. Furthermore, only compound 6 showed high antioxidant activity by using DPPH with an IC50 value of 4.47 μg/mL.

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33

Kumari, N., P. K. Verma, P. N. Pathak, A. Gupta, A. Ballal, V. K. Aswal, and P. K. Mohapatra. "Extractant mediated nano-aggregate formation in Triton X-114 aided cloud formation: structural insights from TEM and SANS studies." RSC Advances 5, no. 116 (2015): 95613–17. http://dx.doi.org/10.1039/c5ra18546g.

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Nanoaggregate formation by self assembly was noticed during the cloud formation of Triton X-114 in the presence of dibenzoylmethane (DBM), thenoyltrifluoroacetone (HTTA) and 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (PMBP) and tributyl phosphate (TBP).

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34

Saida, Keraghel, Benghanem Fatiha, Dehbi Ouarda, Ourari Ali, Ouari Kamel, and Lydia Brelot. "4-[(3-Hydroxyanilino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 26, 2012): o1909—o1910. http://dx.doi.org/10.1107/s1600536812023082.

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In the title compound, C23H19N3O2, the dihedral angles formed by the pyrazolone ring with the three benzene rings are 30.91 (6), 60.96 (4) and 57.01 (4)°. The ligand is in the enamine–keto form and its structure is stabilized by an intramolecular N—H...O hydrogen bond. In the crystal, O—H...N hydrogen bonds link molecules into chains parallel to [01-1].

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35

MARRUGO-GONZALEZ, Alonso Jose, Valery D. ORLOV, and Roberto FERNANDEZ-MAESTRE. "1,3,5-TRIARYL 2-PYRAZOLINES WITH 8-HYDROXYQUINOLINIC SUBSTITUENT: SYNTHESES, PHOTOPHYSICAL PROPERTIES, AND BIOLOGICAL ACTIVITY." Periódico Tchê Química 12, no. 24 (August 20, 2015): 51–62. http://dx.doi.org/10.52571/ptq.v12.n24.2015.51_p_24_pgs_51_62.pdf.

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1,3,5-triaryl-2-pyrazolines are organic luminophores with arylic radicals that show a wide biological activity and are used as liquid scintillators and electro-optic materials. Experimental. Eleven 2-pyrazolines were synthesized from phenylhidrazine and chalcones of the 8-hydroxyquinoline series: 3-(8-hydroxyquinolin-5-yl)-1-(3-R)-phenylprop-2-enone and 1-(8-hydroxyquinolin-5-yl)-3--(3-R)-phenylprop-2-enone, where R = H, CH3, OCH3, N(CH3)2, Cl, Br, and NO2. The structures were confirmed by elemental analysis, IR, 1H-NMR, and electronic spectroscopy. Results and discussion. The 1- and 3-aryl substituents of the pyrazoline ring produced shifts to shorter or longer wavelengths, in absorbance and fluorescence. The electron acceptor hydroxyquinolinic fragment influenced the absorption and luminescence spectra; the possible cause of low quantum yields in pyrazolines (1-phenyl-3-(4-R phenyl)-5-(8-hydroxyquinolinil-5)-2-pyrazoline) may be the specific intramolecular fluorescence quenching in bicromophores, characteristic of 5-acceptor substituted pyrazolines, and, in series (1-phenyl-5-(4-R phenyl)-3-(8-hydroxyquinolinil-5)-2-pyrazoline) of excited-state intramolecular proton transfer (ESIPT) reactions, and the increasing donor-acceptor intramolecular interaction of their excited molecules; Density functional calculations (method PM6) were used to probe the electronic structure and energy ordering of the emissive and the electron-transfer states; PM6 results agreed with the experimental data. 1-phenyl-3-(4-R phenyl)-5-(8-hydroxyquinolinil-5)-2-pyrazoline showed fungistatic and fungicide activities. Additionally, all our pyrazolines showed wide theoretical biological activities.

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36

Kumar, Balbir, Hitesh Mahajan, Satya Paul, Rajni Kant, and Vivek K. Gupta. "Crystal structure of 4-[(2,4-dichlorophenyl)(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)methyl]-5-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (September 30, 2015): o805—o806. http://dx.doi.org/10.1107/s2056989015017880.

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In the title compound C27H22Cl2N4O2, the pyrazol-5-ol ring makes a dihedral angle of 34.80 (11)° with the phenyl ring to which it is bound, while the pyrazolone ring is inclined at 34.34 (12)° to its attached phenyl ring. In the crystal, N—H...O and C—H...Cl hydrogen bonds link the molecules into chains along [010]. Intermolecular π–π interactions are observed between the pyrazolone ring and the phenyl ring bound to the pyrazol-5-ol ring system [centroid–centroid separation = 3.916 (2) Å].

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37

Jordanov, V. M., M. Atanassova, and I. L. Dukov. "SOLVENT EXTRACTION OF LANTHANIDES WITH 1-PHENYL-3-METHYL-4-BENZOYL-5-PYRAZOLONE." Separation Science and Technology 37, no. 14 (January 11, 2002): 3349–56. http://dx.doi.org/10.1081/ss-120006166.

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38

MANCHANDA, V. K., and P. K. MOHAPATRA. "1-Phenyl-3-methyl-4-benzoyl-pyrazolone-5: A Promising Extractant for Plutonium." Separation Science and Technology 29, no. 8 (May 1994): 1073–86. http://dx.doi.org/10.1080/01496399408005618.

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39

Gineinah, Magdy. "6-, 7- AND 8-(5-ARY L-1-PHENYL-2-PYRAZOLIN-3-LY)IMIDAZO- AND PYRIMIDO[2,1-b]BENZOTHIAZOLES AS NOVEL ANTICONVULSANT AGENTS." Scientia Pharmaceutica 69, no. 1 (March 30, 2001): 53–61. http://dx.doi.org/10.3797/scipharm.aut-01-06.

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Some new derivatives of 2-amino-5- and 6-(5-aryl-1-phenyl-2-pyrazolin-3-yl)benzothiazole were synthesized from the corresponding aminophenyl compounds by reaction with KSCN/Br2 to build up the benzothiazole ring. The aminophenyl derivatives of pyrazoline were prepared by cyclization with phenylhydrazine of the appropriate 1,3-diphenyl-2-propen-1-one derivatives obtained from arninoacetophenone and differently substituted aldehydes. However, the newly synthesized 2-aminobenzothiazole derivatives of pyrazoline were subjected to cyclization with ethyl brornopyruvate to afford the formation of 6- and 7-(5-aryl-1 -phenyl-2-pyrazolin-3 -yl)-2-ethoxycarbonylimidazo[2,1-b]benzothiazole derivatives. Furthermore, dimethyl acetylenedicarboxylate (DMAD) was used as another cyclizing agent for 2-aminobenzothiazole derivatives to obtain 7- and 8-(5-aryl-1-phenyl-2-pyrazolin-3-y1)-4-methoxycarbonyl-2-oxo-2H-pyrimido[2,1-b]benzothiazole derivatives. The newly prepared compounds were screened for their anticonwlsant activities. However, some of the tested compounds manifested good anticonvulsant potencies.

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40

Guna, J. V., V. N. Bhadani, H. D. Purohit, and Dipak M. Purohit. "Synthesis and Antimicrobial Activity of (1-Acetyl/1-Phenyl)-3-{4'-[(4'''-Chlorophenyl) (Phenyl) Methyl Amino] Phenyl}-5-Aryl-Pyrazoline." International Letters of Chemistry, Physics and Astronomy 49 (April 2015): 104–8. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.49.104.

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1-Acetyl-3-{4'-[(4'''-chlorophenyl) (phenyl) methyl amino] phenyl}-5-aryl-pyrazolines (3a-3l) and 1-Phenyl-3-{4'-[(4'''-chlorophenyl) (phenyl) methyl amino] phenyl}-5-aryl-pyrazolines (4a-4l) have been synthesized. The products have been assayed for their biological activity against Gram +ve, Gram -ve bacteria and fungi. Some of the compounds showed moderate activity in concentration 50 μg/ml. The structure of the products have been elucidated by IR, 1H-NMR, mass spectral data elemental analysis and Thin layer chromatography.

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41

Abaszadeh, Mehdi, Hassan Sheibani, and Kazem Saidi. "The Condensation of (Chlorocarbonyl)phenyl Ketene with Bisnucleophiles. Synthesis of 4-Hydroxy-5-phenylpyro-[2,3-c]pyrazol-6-ones and Formation of Pyrazolo[1,2-a]pyrazole-triones by Hydrogen Exchange in Unstable Mesoionic Compounds." Australian Journal of Chemistry 63, no. 1 (2010): 92. http://dx.doi.org/10.1071/ch09344.

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The addition of (chlorocarbonyl)phenyl ketene 2 to 5-alkylpyrazol-3(4H)-ones 1 led to the formation of 3-hydroxypyrazolo[1,2-a]pyrazole-dione/pyrazolo[1,2-a]pyrazole-trione derivatives 3. This is ascribed to hydrogen exchange in initially formed unstable, mesoionic pyrazolo[1,2-a]pyrazol-4-ium-5-olates. In contrast, condensation of the same ketene with 3-alkyl-1-phenyl-2-pyrazolin-5-ones 4 afforded 4-hydroxy-3-alkyl-1,5-diphenylpyrano[2,3-c]pyrazol-6-one derivatives 5. The latter reaction provides a new and rapid route to 4-hydroxy-2-pyrones fused to pyrazole rings, in good to excellent yields.

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42

AKAMA, Yoshifumi, Masatsugu KAJITANI, Toru SUGIYAMA, and Akira SUGIMORI. "Crystal Structure of Scandium Complex of 1-Phenyl-3-methyl-4-benzoyl-5-pyrazolone." Analytical Sciences 13, no. 1 (1997): 155–57. http://dx.doi.org/10.2116/analsci.13.155.

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43

Akama, Y., M. Shiro, T. Ueda, and M. Kajitani. "Keto and Enol Tautomers of 4-Benzoyl-3-methyl-1-phenyl-5(2H)-pyrazolone." Acta Crystallographica Section C Crystal Structure Communications 51, no. 7 (July 15, 1995): 1310–14. http://dx.doi.org/10.1107/s0108270194007389.

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44

DING, Huajie, Yanning NIU, Weifan YANG, Yanbing XU, Shuanggui YUAN, Zhi QIN, and Xiaohong ZHOU. "Solvent Extraction Study of233Pa(V) with 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone." Journal of Nuclear Science and Technology 42, no. 9 (September 2005): 839–41. http://dx.doi.org/10.1080/18811248.2004.9726454.

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45

Chandra, N. Srikantamurthy, Shamantha Kumar, B. H. Doreswamy, K. B. Umesha, and M. Mahendra. "N′-Benzoyl-5-methyl-1,3-diphenyl-1H-pyrazole-4-carbohydrazide." Acta Crystallographica Section E Structure Reports Online 69, no. 12 (November 13, 2013): o1769. http://dx.doi.org/10.1107/s1600536813029528.

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In the title compound, C24H20N4O2, the pyrazole ring makes dihedral angles of 47.57 (10)° and 30.56 (11)° with its N-bound and C-bound phenyl groups, respectively. The C—N—N—C group that links the two carbonyls has a torsion angle of 81.5 (2)°. The torsion angles between the carbonyl groups and their adjacent pyrazole and phenyl rings are 125.89 (19) and 164.22 (17)°, respectively. In the crystal, pairs of molecules are linked by N—H...O hydrogen bonds intoR22(10) ring motifs, which in turn link to form chains that propagate parallel to thec-axis direction.

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46

Erdem, Ahmet, Hasan Genc, Nejdet Sen, Rafet Kilincarslan, and Emin Erdem. "The Synthesis and Reactions of Novel Pyrazole Derivatives by 4-phenylcarbonyl-5-phenyl-2,3-dihydro-2,3-furandione Reacted with Some Hydrazones." Revista de Chimie 68, no. 1 (February 15, 2017): 143–46. http://dx.doi.org/10.37358/rc.17.1.5407.

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We report some novel pyrazole derivatives taking 4-phenylcarbonyl-5-phenyl-2,3-dihydro-2,3-furandione, 1. For this, 4-phenylcarbonyl-5-phenyl-2,3-dihydro-2,3-furandione, 1 was reacted with benzaldehyde(2- or 4-fluorophenyl)hydrazone to give 4-benzoyl-1-(2- or 4-fluorophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid 2a,b. Pyrazol derivative containing 2-fluorophenyl group 2a was converted into carboxylic chloride derivative 3a by thionyl chloride and then the compound 4a was obtained from reaction ammonia with compound 3a. In the next step, 4-benzoyl-1-(2-fluorophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid 2a was reacted with MeOH/H2SO4, EtOH/H2SO4, 2-nitrophenylhydrazine and 3-nitrophenylydrazine to give 5a,b and 6a,b pyrazol derivatives, respectively. The structures regarding all compounds synthesized were determined by the IR, NMR and elemental analysis method.

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47

Abdelhamid, Abdou O., and Bahia Y. Riad. "Reactions with 4-Bromo-3-methyl-1-phenyl-2-pyrazolin-5-one: New Fused Pyrazole Derivatives." Archiv der Pharmazie 320, no. 10 (October 1987): 1010–14. http://dx.doi.org/10.1002/ardp.198700003.

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48

Shu-Xiang, Wang, Wang Wei, and Li Ji-Tai. "Synthesis of 1, 4- Dihydropyrano [2, 3-c] pyrazole Derivatives with no Catalyst Under Ultrasound Irradiation." E-Journal of Chemistry 2, no. 2 (2005): 121–25. http://dx.doi.org/10.1155/2005/753642.

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A series of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1, 4-dihydropyrano [2, 3-c]pyrazoles were synthesized in 84%-95% yields by the condensation of aromatic aldehydes, malononitrile with 3-methyl-1-phenyl-2-pyrazolin -5-one with no catalyst under ultrasound irradiation.

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49

Kasimogullari, Rahmi, Belma Zengin, Makbule Maden, Samet Mert, and Cavit Kazaz. "Synthesis of new derivatives of 1-(3-amino-phenyl)-4- benzoyl-5-phenyl-1h-pyrazole-3-carboxylic acid." Journal of the Serbian Chemical Society 75, no. 12 (2010): 1625–35. http://dx.doi.org/10.2298/jsc101018135k.

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4-Benzoyl-1-(3-aminophenyl)-5-phenyl-1H-pyrazole-3- carboxylic acid (1) was synthesized according to the literature.1 2-(3- Aminophenyl)-3,4-diphenyl-2H-pyrazolo[3,4-d]pyridazin-7(6H)-one (5) was obtained by the cyclocondensation reaction of 1 with hydrazine hydrate. New pyrazole derivatives of compounds 1 and 5 were synthesized by their reaction with ?-diketones, ?-ketoesters, ?-naphthol, phenol and various other reagents. The structures of the synthesized compounds were characterized by 1H-NMR, 13C-NMR, IR and Mass spectroscopy, as well as elemental analysis.

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50

Barton, Richard J., Keith E. Johnson, Beverly E. Robertson, F. Wayne Yerhoff, and Shengzhi Hu. "Structures of the pyrazolones formed by oxidative coupling of phenols with 4-aminoantipyrine." Canadian Journal of Chemistry 65, no. 9 (September 1, 1987): 2082–88. http://dx.doi.org/10.1139/v87-345.

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The structures of reaction products between 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and o-cresol, p-cresol, and p-ethylphenol are reported. The reaction of the former compound with phenols is used to estimate the concentration of phenol in potable water supplies. The reaction products are 2,3-dimethyl-4-[4-oxo-2,5-cyclohexadien-1-ylidene)amino]-1-phenyl-3-pyrazolin-5-one (monoclinic, P21/c, red, Z = 4, a = 7.092(1), b = 26.616(2), c = 8.644(2) Å, β = 79.17(3)°, 1432 reflections, R = 0.083, Rw = 0.040), 1,9a-dihydro-1,6,9a-trimethyl-2-phenylpyrazolo[3,4-b][1,4]benzoxazin-3(2H)-one (orthorhombic, Pbca, yellow, Z = 8, a = 18.943(3), b = 12.749(5), c = 13.223(2) Å, 2122 reflections, R = 0.067, Rw = 0.038), and 6-ethyl-1,9a-dihydro-1,9a-dimethyl-2-phenylpyrazolo[3,4-b|[1,4]benzoxazin-3(2H)-one (orthorhombic, Pbca, yellow, a = 18.895(11), b = 12.737(5), c = 14.041(6) Å, Z = 8, 1126 reflections, R = 0.068, Rw = 0.061), respectively. The latter two compounds rearrange to form 1,2,4,10-tetrahydro-1,6-dimethyl-2-phenyl-3H-pyrazolo[3,4-c][1,5]benzoxazepin-3-one (monoclinic, P21/c, white, Z = 8, a = 15.072(4), b = 14.491(4), c = 15.505(3) Å, β = 111.15(1)°, 3416 reflections, R = 0.101, Rw = 0.046) and 6-ethyl-1,2,4,10-tetrahydro-1-methyl-2-phenyl-3H-pyrazolo[3,4-c][1,5]benzoxazepin-3-one (monoclinic, C2/c, white, Z = 8, a = 33.768(3), b = 6.678(1), c = 15.836(2) Å, β = 115.41(1), 2805 reflections, R = 0.076, Rw = 0.043), respectively. The rearrangement is consistent with the observation that the pyrazolone rings of benzoxazinones are strained, as manifested by enlarged perimeters.

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