- Design, synthesis and biological evaluation of novel pyrazolone derivatives as selective butyrylcholinesterase inhibitors with antioxidant activity against Alzheimer's disease
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The butyrylcholinesterase (BuChE) has been a potent target for the treatment of the Alzheimer's disease (AD), but the selective BuChE inhibitor is still lacking in the market. In this study, the pyrazolone structure was found to be a promising pharmacophore targeting BuChE. Thus, a series of pyrazolone-based compounds 5a-p were designed, synthesized and evaluated in vitro for BuChE inhibitory activities, antioxidant activities and blood-brain barrier (BBB) permeabilities. Besides, the compounds 5g, 5h, 5i and 5o with submicromolar IC50 values as well as good BuChE selectivity were chosen to assess their cytotoxicity in PC12 cells. Among them, compound 5i was the most selective BuChE inhibitor (SI: >200) and showed the good abilities to penetrate BBB, scavenge free radicals (1.04 trolox equivalent). Based on above results, compound 5i was selected for molecular docking studies to explain the BuChE selectivity and was considered as a promising lead compound for further investigation in the treatment of AD.
- Cheng, Maojun,Fang, Yuanying,Guo, Jie,Jin, Yi,Liu, Jing,Wan, Yang,Wang, Rikang,Xie, Sai-Sai,Zhang, Zhipeng
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- Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions
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An electrochemical oxidative cross-coupling reaction between 2.5-substituted-pyrazolin-5-ones and ammonium thiocyanate has been developed, which resulted in a series of unprecedented cross-coupling products under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions. It is worth noting that since the resulting cross-coupling products are nearly insoluble in MeCN, the pure product could be afforded without silica gel column purification. In addition, the prepared ammonium oxides are versatile building blocks for synthesizing functionalized pyrazole derivatives.
- Yuan, Yong,Li, Liang-Sen,Zhang, Lin,Wang, Feng,Jiang, Lin,Zuo, Lin,Wang, Qi,Hu, Jian-Guo,Lei, Aiwen
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supporting information
p. 2768 - 2771
(2021/03/23)
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- Catalytic System-Controlled Divergent Reaction Strategies for the Construction of Diversified Spiropyrazolone Skeletons from Pyrazolidinones and Diazopyrazolones
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A catalytic system-controlled divergent reaction strategy was here reported to construct four types of intriguing spiroheterocyclic skeletons from simple and readily available starting materials via a precise chemical bond activation/[n+1] annulation cascade. The tetraazaspiroheterocyclic and trizazspiroheterocyclic scaffolds could be independently constructed by a selective N?N bond activation/[n+1] annulation cascade, a C(sp2)-H activation/[4+1] annulation and a novel tandem C(sp2)-H/C(sp3)?H bond activation/[4+1] annulation strategy, along with a broad scope of substrates, moderate to excellent yields and valuable transformations. More importantly, in these transformations, we are the first time to capture a N?N bond activation and a C(sp3)?H bond activation of pyrazolidinones under different catalytic system.
- Fang, Feifei,Hu, Shulei,Li, Chunpu,Wang, Qian,Wang, Run,Han, Xu,Zhou, Yu,Liu, Hong
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supporting information
p. 21327 - 21333
(2021/08/20)
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- Enantioselective Synthesis of Spiropyrazolone-Fused Cyclopenta[ c]chromen-4-ones Bearing Five Contiguous Stereocenters via (3+2) Cycloaddition
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An enantioselective synthesis of spiropyrazolone-fused cyclopenta[c]chromen-4-ones is demonstrated via a (3+2) cycloaddition reaction. The reactions of 3-homoacylcoumarins and α,β-unsaturated pyrazolones in the presence of the cinchona-alkaloid derived hy
- Khairnar, Pankaj V.,Su, Yin-Hsiang,Edukondalu, Athukuri,Lin, Wenwei
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p. 12326 - 12335
(2021/08/24)
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- Metal-Free Direct C–H Thiolation and Thiocyanation of Pyrazolones
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Metal-free approach for direct C–H thiolation and thiocyanation of N-substituted pyrazolones with disulfides and thiocyanate salts, respectively, are developed. These reactions allow the C–S bond coupling to proceed effectively under mild conditions, providing useful and convenient methods for preparation of a series of 4-thio-substituted pyrazolone analogues, which have potential applications in organic, medicinal and material chemistry. Preliminary mechanistic investigation suggested that radical processes are likely to involve in these transformations.
- Kittikool, Tanakorn,Yotphan, Sirilata
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supporting information
(2020/02/13)
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- Diversity-Oriented Synthesis of Spiropentadiene Pyrazolones and 1 H-Oxepino[2,3- c]pyrazoles from Doubly Conjugated Pyrazolones via Intramolecular Wittig Reaction
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An efficient method for the diversity-oriented synthesis of spiropentadiene pyrazolones and 1H-oxepino[2,3-c]pyrazoles is reported. The methodology attributes O-acylation of phosphorus zwitterions which were formed by a tandem phospha-1,6-addition of PBu3 to α,β,γ,δ-unsaturated pyrazolones, further generating betaine intermediates that preferentially resulted in the aforementioned cyclic products in a diversity-oriented manner. The mechanistic investigations revealed that formation of the betaines is the key step to provide the products via an intramolecular Wittig reaction or an unprecedented δ-C-acylation/cyclization/Wittig reaction.
- Khairnar, Pankaj V.,Wu, Chi-Yi,Lin, Yi-Fang,Edukondalu, Athukuri,Chen, Yi-Ru,Lin, Wenwei
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supporting information
p. 4760 - 4765
(2020/06/25)
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- Organophosphane-catalyzed direct β-acylation of 4-arylidene pyrazolones and 5-arylidene thiazolones with acyl chlorides
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An efficient method for the direct β-acylation of arylidene pyrazolones and thiazolones with acyl chlorides in the presence of a base catalyzed by organophosphanes is reported. A variety of functionalized 4-arylidene pyrazolone and 5-arylidene thiazolone derivatives were prepared under metal-free and mild conditions via a tandem phospha-Michael addition/O-acylation/intramolecular cyclization/rearrangement sequence. Our mechanistic investigations revealed that the reaction is highly stereospecific to provide exclusively cis-isomers, and the methodology can also be scaled up with similar efficacy.
- Khairnar, Pankaj V.,Su, Yin-Hsiang,Chen, Yung-Chang,Edukondalu, Athukuri,Chen, Yi-Ru,Lin, Wenwei
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supporting information
p. 6868 - 6872
(2020/09/15)
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- Synthesis of pyrazolones and pyrazoles via Pd-catalyzed aerobic oxidative dehydrogenation
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A palladium-catalyzed oxidative dehydrogenation reaction in the presence of AMS and base to synthesize pyrazolones and pyrazoles was identified. This method can be utilized to a wide range of substrates, operates under mild react conditions and can give high yields. We believe it could be used as an alternative protocol for the classical dehydrogenation reactions.
- Zhu, Ye-Fu,Wei, Bo-Le,Wei, Jiao-Jiao,Wang, Wen-Qiong,Song, Wei-Bin,Xuan, Li-Jiang
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supporting information
p. 1202 - 1205
(2019/03/29)
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- Syntheses, structure, DNA-binding and DFT studies of a Cu(II) complex based on a pyrazolone derivative
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A Cu(II) complex based on a pyrazolone derivative, 2-hydroxy-N′-((1-(4-methoxyphenyl)-3methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(phenyl)methylene)benzohydrazide (H2L), has been prepared. IR spectra, UV-vis spectra, elemental analysis and single-crystal X-ray diffraction indicate that the Cu(II) complex was mononuclear with the chemical composition of [Cu(HL)Cl]·CH3OH. The Cu(II) compound presented herein exhibits interesting supramolecular characteristics and a novel 3D supramolecular architecture resulted due to the appropriate synergy of multiple intermolecular hydrogen bonds. The interaction of the Cu(II) complex with calf-thymus DNA was investigated by electronic absorption titration as well as EB-DNA competition experiment, and the results indicate that the Cu(II) compound which has a strong affinity for binding DNA is combined with DNA in an embedded manner. Furthermore, Time-Dependent Density Functional Theory calculations (TD-DFT) have been performed on optimized geometries for a better understanding of the electronic transitions in the UV-vis spectra of H2L and Cu(II) complex.
- Xi, Wei,Wang, Cai-Yun,Meng, Huan-Huan,Song, Xue-Qin
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p. 3128 - 3143
(2019/11/22)
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- Structure-activity relationships of pyrazole-4-carbodithioates as antibacterials against methicillin–resistant Staphylococcus aureus
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Methicillin-resistant Staphylococcus aureus (MRSA) is a major cause of serious hospital-acquired infections and is responsible for significant morbidity and mortality in residential care facilities. New agents against MRSA are needed to combat rising resistance to current antibiotics. We recently reported 5-hydroxy-3-methyl-1-phenyl-1H-pyrazole-4-carbodithioate (HMPC) as a new bacteriostatic agent against MRSA that appears to act via a novel mechanism. Here, twenty nine analogs of HMPC were synthesized, their anti-MRSA structure-activity relationships evaluated and selectivity versus human HKC-8 cells determined. Minimum inhibitory concentrations (MIC) ranged from 0.5 to 64 μg/mL and up to 16-fold selectivity was achieved. The 4-carbodithioate function was found to be essential for activity but non-specific reactivity was ruled out as a contributor to antibacterial action. The study supports further work aimed at elucidating the molecular targets of this interesting new class of anti-MRSA agents.
- Majed, Hiwa,Johnston, Tatiana,Kelso, Celine,Monachino, Enrico,Jergic, Slobodan,Dixon, Nicholas E.,Mylonakis, Eleftherios,Kelso, Michael J.
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supporting information
p. 3526 - 3528
(2018/10/15)
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- DABCO-catalyzed silver-promoted direct thiolation of pyrazolones with diaryl disulfides
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A highly efficient protocol for a direct thiolation of N-substituted pyrazolones with diaryl disulfides is described. Using a combination of DABCO and silver(i) acetate, the C-S bond formation proceeds smoothly at room temperature under mild and easy to handle conditions. This synthetic strategy offers a convenient and direct modification of antipyrine and other pyrazolone substrates, giving a series of aryl sulfide-substituted pyrazolone products in moderate to excellent yields.
- Thupyai, Akkharaphong,Pimpasri, Chaleena,Yotphan, Sirilata
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supporting information
p. 424 - 432
(2018/02/06)
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- Copper/Persulfate-Promoted Oxidative Decarboxylative C?H Acylation of Pyrazolones with α-Oxocarboxylic Acids: Direct Access to 4-Acylpyrazolones under Mild Conditions
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A facile and efficient oxidative C?H acylation of N-substituted pyrazolones using α-oxocarboxylic acids as an acyl group source was developed. A combination of Cu(OAc)2 and K2S2O8 enables the reaction to proceed smoothly under air and provides a wide array of 4-acylpyrazolone products in moderate to excellent yields. The mechanism of this transformation is believed to proceed via a copper-induced decarboxylation to form the acyl-copper species. This method provides a convenient and useful route for a direct installation of an acyl moiety into bioactive pyrazolone derivatives, which can be further utilized in many applications. (Figure presented.).
- Kittikool, Tanakorn,Thupyai, Akkharaphong,Phomphrai, Khamphee,Yotphan, Sirilata
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supporting information
p. 3345 - 3355
(2018/09/10)
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- Spirocyclopropanes from Intramolecular Cyclopropanation of Pyranopyrazoles and Pyranopyrimidine-diones and Lewis Acid Mediated (3 + 2) Cycloadditions of Spirocyclopropylpyrazolones
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A robust intramolecular cyclopropanation reaction was first performed on pyranopyrazole and pyranopyrimidine-dione derivatives to obtain spirocyclopropylpyrazolones and barbiturates, using iodosylbenzene (PhIO) or the combination of iodobenzene diacetate (PIDA)/molecular iodine (I2), under mild reaction conditions. Syntheses of functionally and stereochemically diversified, novel spiropyrazolone fused 2-iminothiophene and spiropyrazolone fused pyrroline scaffolds were also demonstrated via Lewis acid catalyzed highly diastereoselective (3 + 2) cycloaddition reactions of the synthesized spiro-cyclopropyl pyrazolones with phenyl isothiocyanate and benzonitrile, respectively.
- Mukherjee, Prasun,Das, Asish R.
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p. 2794 - 2802
(2017/03/14)
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- One-flask synthesis of pyrazolone thioethers involving catalyzed and uncatalyzed thioetherification pathways of pyrazolones
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A one-flask thioetherification of pyrazolones has been demonstrated by transforming several pyrazolones to their corresponding 4-mercaptopyrazolone derivatives and employing them towards cross-coupling with various aromatic and heteroaromatic iodides by applying Pd(OAc)2/xantphos as the catalytic system. The coupling ability of these thiol intermediates with 2,3-dichloropyrazine through an aromatic SN2 pathway has also been established. This methodology provides the use of inexpensive starting materials along with a short reaction time.
- Mukherjee, Prasun,Das, Asish R.
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supporting information
p. 7267 - 7271
(2017/09/25)
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- Enantioselective Michael Addition of Pyrazolin-5-ones to β-CF3-β-Disubstituted Nitroalkenes Catalyzed by Squaramide Organocatalyst
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A highly enantioselective Michael addition of pyrazolin-5-ones with β-CF3-β-disubstituted nitroalkenes catalyzed by bifunctional squaramide has been developed. Various chiral β-CF3-β-5-hydroxy-pyrazolin-3-yl-disubstituted nitroalkane derivatives bearing all-carbon quaternary stereocenter were prepared in good yields (up to 88%) and excellent enantioselectivities (up to 97% ee).
- Lai, Xiaoyan,Zha, Gaofeng,Liu, Wei,Xu, Yan,Sun, Panpan,Xia, Tao,Shen, Yongcun
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supporting information
p. 1983 - 1988
(2016/08/09)
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- The discovery of indole derivatives as novel hepatitis C virus inhibitors
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In this study, a library of in-house small molecule was screened using a HCV cell-based assay and a compound (1) containing an N-protected indole scaffold (NINS) was identified as a novel anti-HCV inhibitor. Through structure activity relationship (SAR) study, it was observed that the racemic inhibitor (10m) displayed good anti-HCV activity (EC50 = 1.02 ± 0.10 μM) with the excellent selectivity index (SI = 45.56). Interestingly, R-enantiomer ((R)-10m) showed better anti-HCV activity and lower cytotoxicity than S-enantiomer ((S)-10m). (R)-10m gave the best anti-HCV potency (EC50 = 0.72 ± 0.09 μM) with the highest selectivity index (SI > 69.44). In addition, the mechanism of action study of NINS derivatives demonstrated that NINS derivatives interfere with the early step (viral entry) of the HCV life cycle.
- Han, Zhiqiang,Liang, Xiao,Wang, Yaxin,Qing, Jie,Cao, Lin,Shang, Luqing,Yin, Zheng
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p. 147 - 155
(2016/04/20)
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- POLYCYCLIC DERIVATIVES TARGETING RAL GTPASES AND THEIR THERAPEUTICAL APPLICATIONS
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Contemplated compounds, compositions and methods are directed to Ral GTPase inhibitors with improved activity.
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Paragraph 0174-0175
(2017/01/02)
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- Novel hybrids of 3-n-butylphthalide and edaravone: Design, synthesis and evaluations as potential anti-ischemic stroke agents
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Abstract Fourteen hybrids (10a-g, 11a-g) of 3-n-butylphthalide (NBP) and edaravone (Eda) analogues have been designed and synthesized as potential anti-ischemic stroke agents. In vitro biological studies showed that compounds 10d and 10g exhibited more potent anti-platelet aggregation than ticlopidine (Ticlid), aspirin (ASP) and NBP. Compound 10g more significantly prevented H2O2-mediated neuronal cell (PC12) death than NBP, Eda or NBP together with Eda. Meanwhile, 10g also possessed potent radical scavenging effects on hydroxyl radical (·OH) and superoxide anion radical (·O2-). Our findings may provide new insights into the development of these hybrids, like 10g, for the intervention of ischemic stroke.
- Sheng, Xiao,Hua, Kai,Yang, Chunyu,Wang, Xiaoli,Ji, Hui,Xu, Jinyi,Huang, Zhangjian,Zhang, Yihua
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p. 3535 - 3540
(2015/08/06)
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- Synthesis, structure and supramolecular properties of 1,7′-bis[4-(3-methyl-2,3-dihydro-pyrazol-1-yl)phenol]-1,4,7-trioxaheptane
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A new pyrazole derivative, 1,7′-bis[4-(3-methyl-2,3-dihydro-pyrazol-1-yl)phenol]-1,4,7-trioxaheptane with m.f. C24H24N4O5 has been synthesized and the crystal structure was determined by single crystal X-ray diffraction. Interestingly, the title compound are linked by intermolecular O2-H22?N2 hydrogen bonds into a 36 atoms' macro-ring which is further held together into one dimensional beaded chain via C-H?O hydrogen bonding between another phenol oxygen atom and one methylene carbon atom.
- Liu, Bao-Yong,Zhang, Bin,Yang, Xi
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p. 1339 - 1341
(2015/02/19)
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- P-Toluenesulphonic acid-promoted, I2-catalysed sulphenylation of pyrazolones with aryl sulphonyl hydrazides
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Aryl pyrazolone thioethers were synthesized via the I2-catalysed cross-coupling of pyrazolones with aryl sulphonyl hydrazides in the presence of p-toluenesulphonic acid, which has been proposed to promote the reaction by facilitating the decomposition of sulphonyl hydrazides. This journal is
- Zhao, Xia,Zhang, Lipeng,Li, Tianjiao,Liu, Guiyan,Wang, Haomeng,Lu, Kui
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supporting information
p. 13121 - 13123
(2014/12/11)
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- Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4- phenoxyquinoline derivatives as potential antitumor agents
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Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant cytotoxicity and high selectivity against HT-29, H460 and A549 cancer cell lines as compared with foretinib. The SAR analyses indicated that compounds with halogen groups, especially trifluoromethyl groups at 2-position on the phenyl ring (moiety B) were more effective. In this study, a promising compound 17 (c-Met IC50 = 2.20 nM, a multi-target tyrosine kinase inhibitor) showed the most potent antitumor activities with IC50 values of 0.14 μM, 0.18 μM, 0.09 μM, 0.03 μM, and 1.06 μM against HT-29, H460, A549, MKN-45, and U87MG cell lines, respectively.
- Zhou, Shunguang,Ren, Jianguo,Liu, Mingmei,Ren, Lixiang,Liu, Yajing,Gong, Ping
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- Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents
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Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant cytotoxicity and high selectivity against HT-29, H460 and A549 cancer cell lines as compared with foretinib. The SAR analyses indicated that compounds with halogen groups, especially trifluoromethyl groups at 2-position on the phenyl ring (moiety B) were more effective. In this study, a promising compound 17 (c-Met IC50= 2.20 nM, a multi-target tyrosine kinase inhibitor) showed the most potent antitumor activities with IC50values of 0.14 μM, 0.18 μM, 0.09 μM, 0.03 μM, and 1.06 μM against HT-29, H460, A549, MKN-45, and U87MG cell lines, respectively.
- Zhou, Shunguang,Ren, Jianguo,Liu, Mingmei,Ren, Lixiang,Liu, Yajing,Gong, Ping
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- Direct and enantioselective vinylogous michael addition of α-alkylidenepyrazolinones to nitroolefins catalyzed by dual cinchona alkaloid thioureas
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While several protocols exist for the asymmetric functionalization of pyrazolinones at the α-position relying on nucleophilic addition or annulation procedures, use of α-alkylidene electron-rich analogues in asymmetric vinylogous coupling to carbon electrophiles is substantially an uncharted domain. We now report, for the first time, that alkylidenepyrazolinones carrying an enolizable carbon at the γ-position efficiently participate in direct and asymmetric, catalytic vinylogous Michael-type additions to nitroolefins providing the expected adducts in high yields, with complete γ-site selectivity and with extraordinary levels of enantio-, diastereo-, and geometrical selectivities. Both enantiomeric adducts were equally accessed by employing a quasi-enantiomeric quinine- or quinidine-based thiourea catalyst pair.
- Rassu, Gloria,Zambrano, Vincenzo,Pinna, Luigi,Curti, Claudio,Battistini, Lucia,Sartori, Andrea,Pelosi, Giorgio,Casiraghi, Giovanni,Zanardi, Franca
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supporting information
p. 2330 - 2336
(2014/07/21)
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- Tungstophosphoric acid-catalyzed synthesis of pyrazolones in water
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A convenient and efficient method for the synthesis of pyrazolones via condensation of hydrazine derivatives with β-keto esters in water catalyzed by tungstophosphoric acid is described. It eliminates the need to dry solvents and substrates before use and the products are easily isolated with high yields.
- Min, Zhen-Li,Hu, Xia-Min
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p. 7290 - 7292
(2013/08/23)
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- Ring-opening polymerization of lactides catalyzed by magnesium complexes coordinated with NNO-tridentate pyrazolonate ligands
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A series of magnesium benzylalkoxide complexes, [LnMg(μ-OBn)] 2 (1-14) supported by NNO-tridentate pyrazolonate ligands with various electron withdrawing-donating subsituents have been synthesized and characterized. X-ray crystal structural studies revealed that Complexes 1-3, 5, 7, 9, and 10 are dinuclear bridging through benzylalkoxy oxygen atoms with penta-coordinated metal centers. All of these complexes acted as efficient initiators for the ring-opening polymerization of L-lactide and rac-lactide. Based on kinetic studies, the activity of these metal complexes is significantly influenced by the electronic effect of the ancillary ligands with the electron-donating substituents at the phenyl rings enhancing the polymerization rate. In addition, the "living" and "immortal" character of 6 has paved a way to synthesize as much as 40-fold polymer chains of polylactides with a very narrow polydispersity index in the presence of a small amount of initiator. Among all of magnesium complexes, Complex 6 exhibits the highest stereoselectivity toward ring-opening polymerization of rac-lactide with Pr up to 88% in THF at 0 °C.
- Chuang, Hui-Ju,Chen, Hsiao-Li,Ye, Jian-Li,Chen, Zn-Yun,Huang, Pei-Ling,Liao, Tzu-Ting,Tsai, Tsung-En,Lin, Chu-Chieh
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p. 696 - 707
(2013/08/24)
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- Straightforward copper-catalyzed synthesis of pyrrolopyrazoles from halogenated pyrazolecarbaldehydes
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Straightforward synthesis of a variety of pyrrolo-fused pyrazoles via a cascade reaction between halopyrazolecarbaldehydes and ethylisocyanoacetate in the presence of copper and a base is described.
- Nayak, Maloy,Batchu, Harikrishna,Batra, Sanjay
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supporting information; experimental part
p. 4206 - 4208
(2012/08/28)
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- Regioselective synthesis of heteroaryl triflones by LDA (lithium diisopropylamide)-mediated anionic thia-Fries rearrangement
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Novel heteroaryl triflones including oxindole, pyrazolone, pyridine, and quinoline derivatives have been regioselectively synthesized by LDA-mediated thia-Fries rearrangement for the first time. These reactions are also the first examples of the application of anionic thia-Fries rearrangement in heteroaromatic compounds.
- Xu, Xiu-Hua,Wang, Xin,Liu, Guo-Kai,Tokunaga, Etsuko,Shibata, Norio
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supporting information; experimental part
p. 2544 - 2547
(2012/07/14)
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- A facile organocatalyzed Michael addition of pyrazolines to α,β-unsaturated carbonyl compounds
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A new highly efficient cascade reaction of pyrazolines with α,β-unsaturated carbonyl compounds catalyzed by DBU was reported. The process underwent the first deprotection/Michael addition reaction to give 4-substituted pyrazoline derivatives, which were further converted into 4,4-di-substituted pyrazolone derivatives through the second deprotection/Michael reaction. The mechanism for this reaction was also studied.
- Xie, Chen,Lu, Zhijin,Zhou, Wei,Han, Jianlin,Pan, Yi
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supporting information
p. 6650 - 6653
(2013/01/15)
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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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- Quinazolin-4-one derivatives
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A medicament having an inhibitory activity against hematopoietic prostaglandin D2 synthase, which comprises as an active ingredient a compound represented by the following general formula (I) or a salt thereof: wherein X represents a group represented by the formula —N═C(R5)— or the formula —NH—CH(R5)—, R1, R2, R3, and R4 represent a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, or a hydroxy group, R5 represents a C1 to C6 alkyl group or a C6 to C10 aryl group, and R represents an amino group.
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Page/Page column 23
(2010/11/24)
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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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- DRUGS COMPRISING COMBINATION OF ANTITHROMBOTIC AGENT WITH PYRAZOLONE DERIVATIVE
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It is intended to provide drugs for treating and/or preventing ischemic diseases which are safe and have little side effects. Namely, drugs comprising a combination of an antithrombotic agent and a pyrazolone derivative defined in the description or its pharmaceutically acceptable salt.
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- 1-Aryl-4-carbamoyl-pyrazolin-5-ones
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Substituted 1-phenyl-4-phenylcarbamoyl-2-pyrazolin-5-ones, e.g. those of the formula STR1 wherein each of R, R' and R" is alkyl, alkoxy, halo or trifluoromethyl, or at most 2 thereof are hydrogen; or their salts with therapeutically acceptable bases, are
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