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Three novel photoisomeric compounds of the 4-acyl pyrazolone derivants: Crystal structures and substituent effects on photo-isomerism in solid state

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Science China Chemistry 2008年第7期51卷 661-668页

作者： WANG JunHua LIU Lang LIU GuangFei GUO JiXi JIA DianZeng Institute of Applied Chemistry Xinjiang UniversityUrumqi 830046China

Three new photoisomeric compounds: 1,3-diphenyl-4-benzal-5-pyrazolone 4-methylthiosemicarbazone (DPBP-MTSC), 1,3-diphenyl-4-(4′-methylbenzal)-5-pyrazolone 4-methylthiosemicarbazone (DP4MBP- MTSC), and 1,3-diphenyl-4-(4′-bromobenzal)-5-pyrazolone 4-methylthiosemicarbazone (DP4BrBP-MTSC) were synthesized by direct condensation of pyrazolones and 4-methylthiosemicarbazone. Their struc- tures were confirmed using 1H NMR, IR, elemental analyses, and X-ray crystallographic analyses. The photoisomeric properties in the solid state were studied under UV light irradiation and the photo- isomerization phenomena were interpreted by the double proton-transfer mechanism. Moreover, the effects of different substituent groups at the 4-position of the benzal in the three compounds on the photoisomeric properties were discussed.

关键词： photoisomerization pyrazolone proton-transfer substitute effects

Synthesis and Crystal Structure of N-(1-Phenyl-3methyl-4-benzal-pyrazolone-5)-furoic Hydrazide

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Chinese Journal of Structural Chemistry 2003年第5期22卷 568-572页

作者： LIULang JIYa-Li JIADian-Zeng YUKai-Bei InstituteofAppliedChemistry XinjiangUniversityUrumqi830046China ChengduInstituteofOrganicChemistry TheChineseAcademyofSciencesChengdu610012China

N-(1-Phenyl-3-methyl-4-benzal-pyrazolone-5)-furoic hydrazide (PMBP-FUH, C22H18N4O3, CCDC No: 188946) has been synthesized and characterized by IR spectrum, 1H NMR and single-crystal X-ray diffraction. The crystal is of orthorhombic, space group Pbca with a = 11.870(2), b = 15.951(3), c = 19.674(3) ? V = 3725.0(11) ?, Mr = 386.40, Z = 8, Dc = 1.378 g/cm3, F(000) = 1616, R = 0.0455 and wR = 0.0809. The inter- or intramolecular hydrogen bonds result in the formation of three-dimensional network structure.

关键词： synthesis crystal structure furoic hydrazide pyrazolone

Microwave-assisted Synthesis and Crystal Structure of 3-Acetamido-1-phenyl-4-(2,6-dichloro)benzylidene-5-pyrazolone

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Chinese Journal of Structural Chemistry 2011年第12期30卷 1782-1786页

作者：游新奎林志兰张雪利高原 College of Chemistry and Chemical Engineering Shenzhen University

The title compound,3-acetamido-1-phenyl-4-（2,6-dichloro）benzylidene-5-pyrazolone（C18H13Cl2N3O2,Mr = 374.21）,has been synthesized by one-step condensation of 2,6-dichloroben-zaldehyde with acetic anhydride and 3-amino-1-phenyl-5-pyrazolone under microwave *** compound was characterized by means of IR and 1H *** crystal and molecular structure were determined by X-ray *** belongs to the orthorhombic system,space group Pbca,with a = 12.5312（13）,b = 8.5495（9）,c = 31.110（3） ,V = 3332.9（6） 3,Z = 8,Dc = 1.492 g/cm3,λ = 0.71073 ,μ（MoKα） = 0.407 mm-1,F（000） = 1536,the final R = 0.0394 and wR = 0.0984.A total of 15894 reflections were collected,of which 3630 were independent（Rint = 0.0362）.There exist three planes in the molecular structure.X-ray analysis reveals that the dihedral angles between planes 1 and 2,1 and 3 and 3 and 2 are 80.89,74.29 and 20.57°,respectively.

关键词： pyrazolone microwave irradiation crystal structure

Study　on　the　Synergistic　Extraction　of　Ytterbium　with　1－Phenyl－3－Methyl－4－（α－Furoyl）－5－pyrazolone　and　Neutral　Extractant

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Journal of Rare Earths 1994年第3期12卷 222-224页

作者：丁中涛刘松愈田应朝 Yunnan Univ Kunming China

The extraction of Yb3+ by HA [1-phenyl-3-methyl-4-(α-furoyl)-5-pyrazolone] and by HA in combination with a neutral extractant B in toluene have been studied, where B represents n-butyloctyl sulfoxide (BOSO), n-pentylhexyl sulfoxide (PHSO), ethyl-n-dodecyl sulfoxide (EDSO), diphenyl sulfoxide (DPSO) or TBP. The composition of the synergistic extraction complexes have been shown to be YbA3·B and their extraction equilibrium constants have been determined separately.

关键词： Ytterbium pyrazolone Synergistic extraction Neutral extractant Asymmetric sulfoxide

Synthesis of Chlorosulfonyl-containing pyrazolone Azo Compounds with Thionyl Chloride-DMF System

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Chinese Journal of Chemical Engineering 2004年第5期12卷 719-722页

作者：汤立军张淑芬崔志华杨锦宗高文涛 State Key Laboratory of Fine Chemicals Dalian University of Technology Dalian 116012 ChinaDepartment of Chemistry Bohai University Jinzhou 121003 China State Key Laboratory of Fine Chemicals Dalian University of Technology Dalian 116012 China Department of Chemistry Bohai University Jinzhou 121003 China

Chlorosulfonyl-containing pyrazolone azo compounds (2a, 2b) have been prepared by reaction of the corresponding sodium sulfonate (1a, 1b) with thionyl chloride in the presence of a catalytic quantity of N,Ndimethylformamide in dry benzene. The effects of reaction temperature, time, catalyst and solvent amount on the yield of 2a and 2b were investigated. The results show that chlorination of 1a and 1b under optimal conditions gives 2a and 2b in 95.5% and 99.2% yield respectively. The given method is facile and suitable for large-scale synthesis.

关键词： azo compounds thionyl chloride chlorination pyrazolone synthesis

In Silico and in Vitro Analysis of pyrazolone Derivatives against Zika Virus and Identification of Potential NS5 Methyltransferase Inhibitors by Molecular Docking

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Journal of Biosciences and Medicines 2024年第7期12卷 214-229页

作者： Luciene Soares Silva Tiago Soares Barbosa Maria Leonisa Sanchez-Nuñez Aldenise Mont Serrat Rosa da Silva Vitor Won-Held Rabelo Leonardo dos Santos Corrêa Amorim Leonardo Alves Miceli Percilene Fazolin Vegi Alice Bernardino Helena Carla Castro Izabel Christina Nunes de Palmer Paixão Science and Biotechnology Graduate Program Department of Cellular and Molecular Biology Institute of Biology Fluminense Federal University Niteri Brazil Science and Biotechnology Graduate Program Department of Cellular and Molecular Biology Institute of Biology Fluminense Federal University Niterói Brazil Laboratory of Antibiotics Biochemistry Teaching and Molecular Modeling Institute of Biology Fluminense Federal University Niterói Brazil Laboratory of Organic Chemistry at the Institute of Chemistry Institute of Biology Fluminense Federal University Niterói Brazil

Zika virus (ZIKV), a mosquito-borne flavivirus, has been associated with benign infections for decades. However, it has become a public health concern due to its association with severe fetal and neurological complications. Although many efforts have been made to control ZIKV infection, approved vaccines or antiviral drugs are still lacking. Consequently, the development of new effective anti-ZIKV agents is urgently needed. In this context, we investigated the antiviral potential of pyrazolone derivatives against ZIKV replication using in silico and in vitro methods. The four pyrazolone derivatives evaluated (1a, 1b, 1c, and 1d) inhibited over 50% of ZIKV replication with low cytotoxicity. Among them, compound 1b exhibited the most potent activity (EC50 = 4.3 μM) and the highest selectivity (SI = 342). Mechanism of action studies indicated that these compounds act at early stages of virus replication, and compound 1b can also directly inactivate ZIKV particles. Molecular docking studies suggested that these compounds can bind to and block the activity of ZIKV NS5 methyltransferase. Finally, pharmacokinetic and toxicological predictions have reinforced the safety and drug-like profiles of these derivatives. In conclusion, the pyrazolone scaffold proved to be valuable for anti-ZIKV drug development, and the derivatives studied deserve further investigation.

关键词： Zika pyrazolone NS5 Methyltransferase Antivirals

pyrazolone synthesis of spiro[naphthalene-2,4’-pyrazole] and spiro[isoquinoline-7,4’-pyrazole] by Michael addition

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Pyrazolone synthesis of spiro[naphthalene-2,4’-pyrazole] an...

Asymmetric cooperative catalysis in the conjugate addition of pyrazolones to nitroolefins and subsequent dearomative chlorination

中国化学会第十三届全国有机合成化学学术研讨会

作者： Yu-Ling Lu Jing Sun Chao-Guo Yan College of Chemistry ＆ Chemical Engineering Yangzhou University

Subunits containing carbonrings、nitrogen heterocycles and spirocyclic structures are common in biologically active *** derivatives,representing an important class of five membered-ring lactams,have exhibited a variety of applications as pharmaceutical agents,synthetic scaffolds in medicinal and synthetic ***,pyrazolin-5-ones derivatives have been well known as analgesic and antipyretic *** a consequence,many diverse methods to access structurally diverse heterocyclic spirooxindoles have been developed during the past few years.

关键词： Michael addition pyrazolone

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Science China Chemistry 2014年第2期57卷 265-275页

作者： ZHANG KeFeng LI Feng NIE Jing MA JunAn Department of Chemistry Tianjin University

Over the past decade many bifunctional amine-thioureas have been developed as active metal-free organocatalysts. Coopera-tive catalysis of these amino-thioureas allows high reaction rates and excellent transfer of stereocbemical information. Despite these impressive advances, the design of new high-performance catalysts for applications in asymmetric catalytic reactions is of ongoing interest in organic chemistry. Herein we describe a cooperative catalyst system consisting of a chiral amine thiourea and an achiral organic acid that promotes the conjugate addition of 4-nonsubstituted pyrazolones to nitroolefins and subsequent dearomative chlorination. The corresponding adducts and the subsequent products were obtained in high to excel lent yields （up to 99%） and high stereoselectivities （up to 99/1 dr, 98% ee） under mild reacton conditions. These transforma tions provide an easy access to enantio-enriched pvrazole derivatives, which could possess Potential oharmaceutical activity.

关键词： cooperative catalysis conjugate addition amine-thioureas pyrazolone nitroolefin chlorination

Visible light-promoted enantioselective aerobic oxidation of pyrazolones by phase transfer catalysis

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Green Synthesis and Catalysis 2022年第1期3卷 102-109页

作者： Yakun Wang Shuaifei Wang Jie Liu Mingming Lian Yifan Chen Ke Wang Yawei Zhang Tao Zhang Lizhen Fang School of Pharmacy Xinxiang Medical UniversityXinxiang 453003China Department of Pharmaceutics Daqing CampusHarbin Medical UniversityDaqing 163319China School of Medical Engineering Xinxiang Medical UniversityXinjiang 453003China

An efficient and enantioselective aerobic oxidation of 4-substituted pyrazolones has been developed by phase transfer *** visible light as the driving force and O_(2)(in air)as the oxidant,broad scopes(38 examples)of pyrazolones bearing an oxygen-attached carbon stereocenter at C-4 position were obtained in high yields(up to 98%)and excellent enantioselectivities(up to 93%ee)under mid *** ready availability of catalyst,ease of operation,and low-cost and eco-friendly nature highlighted the practical utility of this visible lightpromoted enantioselective aerobic oxidation.

关键词： Aerobic oxidation pyrazolone Visible light Phase transfer catalysis Cinchona alkaloid