cas 89-25-8, 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one

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Structure and extractive ability of 1-alkyl- and 3-methyl-1-phenyl-2- pyrazolin-5-ones
Extractive ability of 1-substituted 3-methylpyrazol-5-ones (LH) is studied. From acidic chloride complexes, ionic thallium(III) associates (LH 2)[TlCl4] are extracted; from trichloroacetate, coordination scandium complexes Sc(LH)4(CCl3COO) 3; and from ammine, copper(II) complexes CuL2. The extractive ability decreases in the order R = C7H15 > C6H13 > C5H11 > C 6H5 > C4H9. 2005 Pleiades Publishing, Inc.
Lesnov,Sazonova,Pavlov
p. 298 - 302
(2005)
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Synthesis and crystal structure of 5-chloro-3-methyl-1-phenyl-1H-pyrazole- 4-carbaldehyde
The title compound, 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 2, was prepared in a series of syntheses to produce new pyrazole derivatives, and its crystal structure was determined by X-ray diffraction method. The crystal belongs to monoclinic
Xu, Cun-Jin,Shi, Yan-Qin
p. 1816 - 1819
(2011)
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Synthesis and Herbicidal Activity of 5-Heterocycloxy-3-methyl-1-substituted-1H-pyrazoles
With the objective of finding valuable herbicidal candidates, a series of new 5-heterocycloxy- 3-methyl-1-substituted-1H-pyrazoles were synthesized and their herbicidal activities were evaluated. The bioassay results showed that some compounds exhibited e
Kang, Jing,Yue, Xia Li,Chen, Chang Shui,Li, Jian Hong,Ma, Hong Ju
(2016)
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Click inspired novel pyrazole-triazole-persulfonimide & pyrazole-triazole-aryl derivatives; Design, synthesis, DPP-4 inhibitor with potential anti-diabetic agents
This work presented the first report on designing, synthesizing of novel pyrazole-triazole-persulfonimide (7a-i) and pyrazole-triazole-aryl derivatives (8a-j) via click reaction using CuI catalyst and evaluated for their anti-diabetic activity and DPP-4 i
Nidhar, Manisha,Khanam, Shaziya,Sonker, Priyanka,Gupta, Priya,Mahapatra, Archisman,Patil, Swaraj,Yadav, Brijesh Kumar,Singh, Rahul Kumar,Kumar Tewari, Ashish
supporting information

(2022/01/22)

Preparative, mechanistic and tautomeric investigation of 1-phenyl and 1-methyl derivative of 3-methyl-5-pyrazolone
1-Phenyl and 1-methyl derivative of 3-methyl-5-pyrazolone were prepared quantitatively via a scalable solvent-free reaction of corresponding hydrazine derivative with ethyl acetoacetate. Different mechanisms have been proposed for the reaction of hydrazine derivatives (methyl or phenyl) with ethyl acetoacetate and also the tautomeric aspects of the targeted compounds have been discussed. Graphical abstract: [Figure not available: see fulltext.] Synopsis: 13C NMR and quantitative proportional amount of different tautomeric forms of 1,3-dimethyl-5-pyrazolone in DMSO-d6.
Fakhraian, Hossein,Nafari, Yaser
(2021/04/19)

Edaravone preparation method
To the preparation method of edaravone, hydrazine and ethyl acetoacetate are taken as raw materials to carry out cyclization reaction under a solvent-free condition, and water is reduced. The acetic acid, absolute ethyl alcohol and other solvents are intr
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Paragraph 0014; 0026-0045

(2021/10/27)

Edaravone preparation method
The edaravone preparation method comprises the following steps: S1) mixing phenylhydrazine and ethyl acetoacetate, and carrying out solvent-free reaction. S2) After the end of the reaction. A solvent is added to the reaction system for crystallization and
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Paragraph 0026-0042

(2021/11/26)

Design, synthesis, antibacterial evaluation and molecular docking studies of novel pyrazole/1,2,4-oxadiazole conjugate ester derivatives
The development of new antimicrobial drugs is most needed due to rapid growth in global antimicrobial resistance. Thus, in this context, a series of novel pyrazole/1,2,4-oxadiazole conjugate ester derivatives (7a–j) was synthesized. All the derivatives we
Depa, Navaneetha,Erothu, Harikrishna
p. 1087 - 1098
(2021/02/26)

Scale-Up of a Continuous Manufacturing Process of Edaravone
Edaravone belongs to a class of brain-protective agents, which can scavenge free radicals. To reduce impurities and improve the yield, a continuous flow production process of edaravone was developed. The synthesis is continuously carried out in two steps. The throughput can reach 11.328 kg/day and the purity of the final product is 99.95%, which are in accordance with the needs of production. This is an efficient and quick production process suitable for industrial production.
He, Yan,Hong, Qingxia,Mei, Wenliu,Sun, Tiemin,Wu, Chengjun,Zhou, Shuhao
p. 2146 - 2153
(2021/09/13)

Preparation method of brain protective agent and key impurities thereof
The invention relates to a preparation method of a brain protective agent and key impurities thereof. According to the invention, phenylhydrazine and ethyl acetoacetate serve as raw materials, edaravone and three key impurities of edaravone are synthesized in the same route, wherein the three key impurities include a transition-state impurity, edaravone dimer nitrogen oxide and 5-methyl-2-phenyl-4-(propyl-2-iene)-2,4-dihydro-3H-pyrazol-3-one; compared with respective synthesis of edaravone and each impurity, the method has the advantage that time and cost are saved; and experiments prove that the method of preparing edaravone by firstly controlling the process for synthesizing the transition-state impurities and then changing the process are higher in the yield and the purity of edaravone compared with direct synthesis of edaravone.
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Paragraph 0023; 0038; 0041; 0043; 0048; 0051; 0052; 0055

(2021/07/08)

Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy
Serine, the source of the one-carbon units essential for de novo purine and deoxythymidine synthesis plays a crucial role in the growth of cancer cells. Phosphoglycerate dehydrogenase (PHGDH) which catalyzes the first, rate-limiting step in de novo serine biosynthesis has become a promising target for the cancer treatment. Here we identified H-G6 as a potential PHGDH inhibitor from the screening of an in-house small molecule library based on the enzymatic assay. We adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest. Collectively, our results suggest that b36 is a novel PHGDH inhibitor, which could be a promising modulator to reprogram the serine synthesis pathway and might be a potential anticancer lead worth further exploration.
Gou, Kun,Luo, Youfu,Luo, Yuan,Sun, Qingxiang,Tan, Yuping,Tao, Lei,Zhao, Yinglan,Zhou, Xia,Zhou, Yue,Zuo, Zeping
(2021/07/26)

Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones
The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.
Wang, Rong-Hui,Li, Ya-Ling,He, Hong-Jiao,Xiao, You-Cai,Chen, Fen-Er
supporting information
p. 4302 - 4306
(2021/02/16)

Catalytic System-Controlled Divergent Reaction Strategies for the Construction of Diversified Spiropyrazolone Skeletons from Pyrazolidinones and Diazopyrazolones
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,Han, Xu,Hu, Shulei,Li, Chunpu,Liu, Hong,Wang, Qian,Wang, Run,Zhou, Yu
supporting information
p. 21327 - 21333
(2021/08/20)

Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions
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
supporting information
p. 2768 - 2771
(2021/03/23)

Preparation method of edaravone
The invention discloses a preparation method of edaravone. The preparation method comprises the following steps: in the presence or absence of a solvent, phenylhydrazine and ethyl acetoacetate are subjected to a cyclization reaction in a continuous flow r
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Paragraph 0052-0075

(2020/11/12)

Tunable optical properties of push-pull chromophores: End group effect
A series of A-π-D-π-A type symmetrical push-pull chromophores with various end groups (e.g., trifluoroacetone, indanone, dicyano, isoxazolone and pyrazolinone) linked through a symmetric π-conjugated backbone (EDOT-phenylene vinylene-EDOT) was synthesized
Tonga, Murat
supporting information

(2020/07/15)

Synthesis of 1,3,5-Trisubstituted Pyrazoles and Hydrazones Using Fe3O4?CeO2 Nanocomposite as an Efficient Heterogeneous Nanocatalyst
Abstract: Pyrazoles and hydrazones, as two significant kinds of potentially bioactivecompounds, were produced with good to excellent yields by condensation ofβ-dicarbonyl compounds with hydrazines in aqueous media in the presence ofFe3O4?CeO2nanocomposite as an efficient heterogeneous nanocatalyst. The magneticnanocatalyst can readily be separated using an external magnet and reused atleast six times without significant loss in activity. The products werecharacterized by IR and 1H and13C NMR spectra.
Hassani, H.,Jahani, Z.
p. 485 - 490
(2020/04/27)

Edaravone compound and pharmaceutical composition thereof
The invention provides an edaravone compound and a pharmaceutical composition thereof. The edaravone compound is prepared by the following steps: sequentially adding absolute ethyl alcohol and phenylhydrazine, dropwise adding tert-butyl acetoacetate for reaction and crystallization, adding an obtained crystal into absolute ethyl alcohol, carrying out heating, refluxing, decolorizing and filtering,and standing a filtrate for crystallization so as to obtain the edaravone compound. The edaravone compound is dertermined by using a powder X-ray diffraction determination method; an X-ray powder diffraction pattern represented by a diffraction angle of 2theta +/- 0.2 degrees shows characteristic diffraction peaks at 11.72 degrees, 14.15 degrees, 17.27 degrees, 20.04 degrees, 24.79 degrees, 29.46degrees and 36.13 degrees; and the edaravone prepared by using the method provided by the invention is high in purity, stable in process, low in cost and applicable to industrial production.
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Paragraph 0009; 0065-0068

(2020/06/02)

Design and Synthesis of Novel Pyrazolo[3,4-d]Pyrimidines: In Vitro Cytotoxic Evaluation and Free Radical Scavenging Activity Studies
With evident biological importance, a new series of pyrazolo[3,4-d]pyrimidines 3a,3b and 4a,4b were synthesized via the formation of pyrazol-3-one 2a and 2b substrates. All compounds were evaluated for in vitro cytotoxic activity against MCF-7 (breast ade
Alharthy, Rima D.
(2020/06/21)

Synthesis and biological evaluations of monocarbonyl curcumin inspired pyrazole analogues as potential anti-colon cancer agent
Purpose: The monocarbonyl analogs of curcumin (MCACs) have been widely studied for their promising antitumor activity. Pyrazole is a five-membered aromatic heterocyclic system with various bioactivities incorporated frequently in drugs. However, few of MCACs inspired pyrazole analogues were investigated. To search for more potent cytotoxic agents based on MCACs, a series of new 1,5-diaryl/heteroaryl-1,4-pentadien-3-ones inspired pyrazole moiety was synthesized and evaluated on their anti-colon cancer activities. Methods: Fifteen new compounds were synthesized and characterized by spectral datum, and then they were tested preliminarily by MTT assay for their cytotoxic activities against a panel of four human cancer cell lines, namely, gastric (SGC-7901), liver (HepG2), lung (A549), and colon (SW620) cancer cells. Compound 7h exhibited excellent selectivity and outstanding anti-proliferation activity against SW620 cells among these 15 compounds. Further, the mechanisms were investigated by transwell migration and invasion assay, clonogenic assay, cell apoptosis analysis, cell cycle analysis, Western blot analysis. Results: The IC50 value of 7h against SW620 cells was 12 nM, being more potent than curcumin (IC50 = 9.36 μM), adriamysin (IC50 = 3.28 μM) and oxaliplatin (IC50 = 13.33 μM). Further assays showed that 7h inhibited SW620 cell migration, invasion and colony formation obviously, which was due to its ability to induce cell cycle arrest in the G2/M and S phases and apoptosis. Western blot assay revealed that 7h decreased the protein expression of ATM gene, which may primarily contribute to its anticancer activity against SW620 cells. Conclusion: A new MCACs 7h was synthesized and found to exhibit excellent anti-proliferation activity against SW620 cells. Further studies indicated that 7h exerted its anticancer activity against SW620 cells probably via decreasing the ATM protein expression. The present study suggested that 7h was a promising candidate as an anti-colon cancer drug for future development.
Hong, Xing,Hu, Xiamin,Min, Zhenli,Ye, Min,Yu, Zhijun,Yuan, Qiong,Zhu, Yue
p. 2517 - 2534
(2020/07/04)

Synthesis and cytotoxic evaluation of some substituted 5-pyrazolones and their urea derivatives
In this paper, a series of new substituted-5-pyrazolones were first synthesized, then formulated by the Vilsmeier–Haack reaction to obtain substituted-4-carbaldehyde-5-pyrazolones. In the final step, when urea was reacted with formulated pyrazolones, we found that, instead of the C=N bond in azomethine form, the compounds tautomerized to form a series of novel pyrazole-4ylidenemethylurea structures. The structures of these compounds were elucidated by FTIR, 1H, 13C NMR, LC-MS/MS, and elemental analysis methods. The cytotoxic and antioxidant effects of substituted 5-pyrazolones and their pyrazolone-urea derivatives were investigated in metastatic A431 and noncancerous HaCaT human keratinocytes by a mitochondrial activity test. The effects of the compounds on the migration of cancerous and noncancerous cell lines were investigated by using a cell scratch assay. The General Linear Model, Statistical Package for Social Sciences (SPSS v26) was used to determine if there was a statistically significant difference between the control and the treatment groups. Four of the nine compounds showed an antioxidant effect. All 5-pyrazolone-urea compounds showed higher toxicity (p 0.05) in cancerous A431 cells compared to noncancerous cells at all time points. All compounds also showed a biphasic hormetic effect. Four of the nine compounds inhibited cell migration.
Erturk, Aliye Gediz,Omerustaoglu, Hilal
(2020/02/22)

"on water" palladium catalyzed diastereoselective boronic acid addition to structurally diverse cyclopropane nitriles
An efficient palladium catalyzed diastereoselective addition of arylboronic acids to complex spirocyclopropyl dinitriles is developed in the presence of a catalytic amount of 4-dodecylbenzenesulphonic acid (DBSA) as a Br?nsted acid surfactant in aqueous media. The protocol is also found to be highly effective when different types of nitrile compounds and organo-boron compounds are used. The overall reaction has been found to be very cost efficient since it requires low catalyst loading, mild thermal energy and short reaction time. Wide substrate scope, operational simplicity, good to excellent product yield, and use of green solvents make the reaction a practical route to transform nitrile into a keto functionality in biorelevant heterocyclic scaffolds. The scale-up synthesis of the target scaffolds can also be achieved with ease which also signifies the practicability of this protocol. This journal is
Das, Asish R.,Das, Dwaipayan,Mukherjee, Prasun
p. 8886 - 8898
(2020/11/23)

Preparation method of edaravone
The invention discloses a preparation method of edaravone. The method comprises the steps as follows: in a mixed solvent (alcohols and water), phenylhydrazine and ethyl acetoacetate react under the action of a catalyst to prepare edaravone, then, edaravon
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Paragraph 0012-0021

(2019/02/08)

Preparing method of edaravone
The invention relates to a preparing method of edaravone, and belongs to the technical field of preparation of heterocyclic compounds. The preparing method of edaravone comprises the steps of carryingout a reaction between phenylhydrazine and ethyl acetoa
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Paragraph 0055-0104

(2019/04/26)

Synthesis of pyrazolones and pyrazoles via Pd-catalyzed aerobic oxidative dehydrogenation
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
supporting information
p. 1202 - 1205
(2019/03/29)

Combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement to construct homoallyl sulfur-containing pyrazolones
The first sequentially combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement reaction of α-alkylidene pyrazolinones and propargyl sulfonium salts has been reported to construct homoallyl sulfur-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones function as N-nucleophilic agents distinguished from the reported C-addition reactions. Propargyl sulfonium salts were first involved in the [2,3]-sigmatropic rearrangement protocol differentiated from the well-established annulation reactions. The excellent regioselectivity, the broad scope of substrates, gram-scale synthesis and convenient transformation embody the synthetic superiority of this cascade process.
Shen, Shou-Jie,Du, Xiao-Li,Xu, Xiao-Li,Wu, Yue-Hua,Zhao, Ming-gang,Liang, Jin-Yan
p. 34912 - 34925
(2019/11/14)

Regioselectivity Switch in Palladium-Catalyzed Allenylic Cycloadditions of Allenic Esters: [4+1] or [4+3] Cycloaddition/Cross-Coupling
The first Pd-catalyzed asymmetric allenylic [4+1] cycloaddition was successfully developed. Alternatively, tuning the Pd catalyst switched the reactivity toward an unprecedented [4+3] cycloaddition/cross-coupling. Ligands play a vital role in controlling the reaction pathway, allowing highly selective access to different products from identical substrates. Biological evaluation of the obtained compounds led to the discovery of new antitumor targets. A possible mechanism is proposed, suggesting two interesting catalytic cycles for the cycloaddition with palladium-butadienyls. This study also demonstrated the potential and utility of allenic esters as 1,4-biselectrophiles and C4 synthons for participating in cycloaddition reactions.
Li, Long,Luo, Pengfei,Deng, Yuhua,Shao, Zhihui
supporting information
p. 4710 - 4713
(2019/03/08)

Phenylacrylate derivative and application thereof as neuroprotective drug
The invention discloses a phenylacrylate derivative and application thereof as a neuroprotective drug, the phenylacrylate derivative and a medicinal preparation thereof have a good curative treating effect on cranial nerve injury diseases such as cerebral apoplexy and related diseases, are low in acute toxicity and do not have the potential heart toxicity risk, and have a prominent technical effect and a substantial scientific progress compared with existing medicines. The phenylacrylate derivative is a compound represented by a general formula i or a salt thereof as shown in the specification.
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Paragraph 0037; 0039

(2019/05/02)

Application and developing of iron-doped multi-walled carbon nanotubes (Fe/MWCNTs) as an efficient and reusable heterogeneous nanocatalyst in the synthesis of heterocyclic compounds
Iron-doped multi-walled carbon nanotubes (Fe/MWCNTs) is an efficient, ecofriendly and reusable heterogeneous nanocatalyst for the one-pot synthesis of heterocyclic compounds including bis-spiro piperidines, piperidines, dihydro-2-oxopyrroles, pyrazoles and diazepines at room temperature with good to excellent yields. The heterogeneous nanocatalyst was fully characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), inductively coupled plasma (ICP) and FT-IR analysis. Also, the structures of all prepared compounds were characterized by 1H NMR, 13C NMR, FT-IR, mass spectrometry (MS) and elemental analysis. The major advantages of these protocols are mild and green reaction conditions, short reaction times, clean reaction, operational simplicity, easy purification and good to excellent yields with the reusable heterogeneous nanocatalyst. The catalyst was ten recycled without significant loss of activity.
Sharghi, Hashem,Aboonajmi, Jasem,Mozaffari, Mozhdeh,Doroodmand, Mohammad Mahdi,Aberi, Mahdi
(2017/11/16)

With herbicidal active pyrazole ether compounds and the use thereof
The invention relates to the technical field of herbicides, and particularly discloses a pyrazole ether compound with herbicidal activity and application thereof. The pyrazole ether compound with the herbicidal activity is a general-formula compound, and the specification specifically discloses 12 kinds of compounds. An experiment result shows that the general-formula compound has high biological activity on weeds and it is hopeful that the pyrazole ether compound serves as herbicide in agriculture and other fields.
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Paragraph 0035; 0036; 0037; 0039; 0040; 0041

(2018/10/19)

Pyrazolone and synthetic method of derivative of pyrazolone
The invention relates to pyrazolone and a synthetic method of a derivative of pyrazolone. The method comprises the steps of preparing acetylacetamide with ketene dimer and ammonium hydroxide being rawmaterials in an ammoniation phase; directly adding substituted hydrazine into an ammoniation kettle to be subjected to a condensation reaction in a condensation phase; adopting concentrated hydrochloric acid to adjust the PH to promote proceeding of a ring-closure reaction in a ring-closure phase; using a cleaning solvent to conduct cleaning to obtain a purified product during aftertreatment. According to the synthetic method, a one-pot method is utilized to synthesize a pyrazolone compound free of solvents, since no solvents exist, the separation and purification process of the product are easily carried out, green production of fine chemicals is effectively achieved, the operation is convenient, the reaction time is obviously shortened, high yield of the product with excellent appearance is achieved, the product yield is increased, the product quality is improved, the yield can reach 88%-98%, and the purity can reach 96%-98%; meanwhile, drainage of wastewater is greatly reduced, andthe problems that the environment pollution is caused, the health of the human kind is harmed, and resources are wasted when water serves as a solvent are fundamentally solved.
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Paragraph 0021; 0022

(2018/03/26)

Bisphosphine catalyzed sequential [3 + 2] cycloaddition and Michael addition of ynones with benzylidenepyrazolones: Via dual α′,α′-C(sp3)-H bifunctionalization to construct cyclopentanone-fused spiro-pyrazolones
A bisphosphine-catalyzed sequential [3 + 2] cycloaddition and Michael addition reaction of ynones with benzylidenepyrazolones has been developed. Under the catalysis of DPPB [1,4-bis(diphenylphosphino)butane], the reaction proceeded smoothly to give spiro-[cyclopentanone] pyrazolone derivatives in moderate to good yields with good diastereoselectivities via sequential dual α′,α′-C(sp3)-H bifunctionalization annulation. This strategy provides a novel route toward the synthesis of spiro-[cyclopentanone] pyrazolones containing three contiguous stereocenters which possess potential pharmaceutical activities.
Zhang, Jiayong,Miao, Zhiwei
supporting information
p. 9461 - 9471
(2019/01/03)

Covalent inhibitors of LgtC: A blueprint for the discovery of non-substrate-like inhibitors for bacterial glycosyltransferases
Non-substrate-like inhibitors of glycosyltransferases are sought after as chemical tools and potential lead compounds for medicinal chemistry, chemical biology and drug discovery. Here, we describe the discovery of a novel small molecular inhibitor chemot
Xu, Yong,Smith, Ruth,Vivoli, Mirella,Ema, Masaki,Goos, Niina,Gehrke, Sebastian,Harmer, Nicholas J.,Wagner, Gerd K.
p. 3182 - 3194
(2017/05/29)

Metal- and solvent-free, iodine-catalyzed cyclocondensation and C[sbnd]H bond sulphenylation: A facile access to C-4 sulfenylated pyrazoles via a domino multicomponent reaction
We describe herein a green and efficient MCRs protocol to synthesize C-4 sulfenylated pyrazoles by iodine-catalyzed cyclocondensation and direct C[sbnd]H bond sulphenylation reactions. Through this protocol, two new C[sbnd]N bonds and one C[sbnd]S bond ar
Sun, Pengfei,Yang, Daoshan,Wei, Wei,Sun, Xuejun,Zhang, Wenhui,Zhang, Hui,Wang, Yu,Wang, Hua
p. 2022 - 2029
(2017/03/17)

AGENT FOR PREVENTING AND/OR TREATING OPHTHALMOLOGIC DISEASES
It is an object of the present invention to provide a novel medicament for preventing and/or treating ophthalmologic diseases caused by ocular angiogenesis. According to the present invention, provided is a medicament for preventing and/or treating ophtha
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Paragraph 0115; 0116; 0117

(2017/10/10)

Synthesis and crystal structure of (2-chloro-4-(phenylthio)phenyl) (3-methyl-1-phenyl-5-(phenylthio)-1H-pyrazol-4-yl)methanone
(2-Chloro-4-(phenylthio)phenyl)(3-methyl-1-phenyl-5-(phenylthio)-1H-pyrazol-4-yl)methanone was obtained by accident. In order to know the structure of this product, the compound was isolated by column chromatography and recrystallized from EtOH. The compo
Sun,Zhai,Sun,Tan,Weng,Liu
p. 1663 - 1667
(2018/02/09)

Phenylhydrazone compound and preparing method, detection method and application thereof
The invention relates to a phenylhydrazone compound and a preparing method, detection method and application thereof. The phenylhydrazone compound is shown as the formula (I), and is a related substance generated in the edaravone synthetic process. The preparing method includes the steps that phenylhydrazine, ethyl acetoacetate and sodium hydrogen sulfite are added into water or an organic solvent, the mixture is reacted, and after the reaction is completed, silica column chromatography separation is carried out, and the phenylhydrazone compound is obtained. The invention also provides a method for measuring the phenylhydrazone compound, edaravone and related substrates thereof with the high-performance liquid chromatography method, the method is easy and convenient to operate, and the measuring result is accurate and reliable. The phenylhydrazone compound can serve as an impurity reference substance to be used for related substance inspection of edaravone raw-material medicine and a preparation thereof, the quality of an edaravone product is controlled, and the safety and the controllability are improved. The formula is defined in the specification.
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Paragraph 0048; 0049; 0050; 0051; 0052; 0053-0060

(2017/06/02)

Spirocyclopropanes from Intramolecular Cyclopropanation of Pyranopyrazoles and Pyranopyrimidine-diones and Lewis Acid Mediated (3 + 2) Cycloadditions of Spirocyclopropylpyrazolones
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.
p. 2794 - 2802
(2017/03/14)

Compounding method for edaravone
The invention belongs to the field of chemical compounding and particularly relates to a compounding method for edaravone. The compounding method comprises the following steps: (1) by taking aniline as a raw material, performing diazotization, reduction and acidification processes, thereby acquiring phenylhydrazine hydrochloride; (2) adjusting pH of phenylhydrazine hydrochloride, and then directly carrying out contracting ring-closure reaction with ethyl acetoacetate, without adding any other solvents in this process, thereby acquiring the product edaravone. According to the compounding method provided by the invention, aniline with lower cost is taken as the initial raw material, phenylhydrazine hydrochloride is firstly compounded, and then phenylhydrazine hydrochloride and ethyl acetoacetate directly have contracting ring-closure reaction under a backflow condition so as to compound edaravone, no solvent is added, a large amount of pollution discharge quantity in the middle link is reduced and the raw material cost is lowered. According to the compounding method provided by the invention, the raw materials are simple, the cost is lower, the reaction condition is mild, the reaction is almost quantitatively completed, the acquired edaravone crude product is higher in purity, the edaravone crude product can meet the medicinal standard after the simple recrystallization process, and the compounding method is suitable for the requirement of industrial production.
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Paragraph 0006; 0020; 0030; 0031; 0032; 0037-0039; 0044-0046

(2017/06/02)

One-flask synthesis of pyrazolone thioethers involving catalyzed and uncatalyzed thioetherification pathways of pyrazolones
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.
supporting information
p. 7267 - 7271
(2017/09/25)

Preparation method for 1-(3-methyl-1-phenyl-1H-pyrazole-5-yl)piperazine
The invention discloses a preparation method for 1-(3-methyl-1-phenyl-1H-pyrazole-5-yl)piperazine. The method uses phenylhydrazine and ethyl acetoacetate as starting materials, and obtains a compound I through cyclization, chloride acetylation, substituti
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Paragraph 0023; 0024; 0025

(2016/10/08)

Microwave-accelerated and Catalyst-free Synthesis of Novel tris-(Pyrazolyl)methanes
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Beyrati, Maryam,Hasaninejad, Alireza
p. 393 - 400
(2016/09/14)

Application of Fe3O4@SiO2@sulfamic acid magnetic nanoparticles as recyclable heterogeneous catalyst for the synthesis of imine and pyrazole derivatives in aqueous medium
Sulfamic acid supported on Fe3O4@SiO2 superpara magnetic nanoparticles was successfully applied as a recyclable solid acid catalyst with a large density of sulfamic acid groups for the synthesis of pyrazole derivatives, an important class of potentially bioactive compounds. The products are obtained in high yield from the one-pot reaction procedure involving dicarbonyl compounds and hydrazines/hydrazides. This new method totally avoids the use of toxic or expensive solvents and organic acids in this reaction.
Zakerinasab,Nasseri,Hassani,Samieadel
p. 3169 - 3181
(2016/04/05)

Enantioselective Michael Addition of Pyrazolin-5-ones to β-CF3-β-Disubstituted Nitroalkenes Catalyzed by Squaramide Organocatalyst
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
supporting information
p. 1983 - 1988
(2016/08/09)

Preparation method of 1-aryl-3-substituent-5-pyrazolone compound
The invention relates to a preparation method of a 1-aryl-3-substituent-5-pyrazolone compound, and discloses a method for synthesizing a 1-aryl-3-substituent-5-pyrazolone compound. Substituted phenylhydrazine with the structure of ArNHNH2 and beta-keto ester with the structure of R2COCH2COOR3 serve as raw materials, water serves as a solvent, and the 1-aryl-3-substituent-5-pyrazolone compound with a moderate to high yield is obtained in the absence of a catalyst. The solvent which is free of toxicity, good in safety and environmentally friendly is used in the method, a moderate to high yield can be achieved, and the method is simple and easy and convenient to implement.
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Paragraph 0023-0024

(2017/04/03)

ANTI-CANCER COMPOUNDS TARGET RAL GTPASES AND METHODS OF USING THE SAME
Methods of inhibiting the growth or metastasis of a cancer in a subject by inhibiting a Ral GTPase in the subject, and small molecule inhibitors of Ral GTPases useful in the methods of the invention. Pharmaceutical compositions containing the compounds of the invention, and methods of using the same.
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Page/Page column 36; 37

(2016/04/26)

Anti-cancer compounds targeting Ral GTPases and methods of using the same
The invention provides methods of inhibiting the growth or metastasis of a cancer in a mammal by inhibiting a Ral GTPase in the mammal. The invention also provides small molecule inhibitors of Ral GTPases useful in the methods of the invention and pharmaceutical compositions containing the therapeutically effective compounds of the invention, and methods of using the same.
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Page/Page column 55;63

(2016/06/28)

Synthesis of novel Ral inhibitors: An in vitro and in vivo study
Chemical synthesis was performed to produce a series of 6-amino-1,3-disubstituted-4-phenyl-1,4-dihydro pyrano[2,3-c]pyrazole-5-carbonitrile compounds (14–57) which were characterized by1H NMR,13C NMR and LC/MS–MS. These compounds were assessed for their effect on the in vitro anchorage independent growth of human lung cancer cell line H2122 and IC50values calculated. Two of the more potent compounds, BQU057 40 and BQU082 57 also displayed a dose dependent effect on RalA and RalB activity in H2122 spheroids using the common RalBP1 pull-down assay. Mouse PK and tissue distribution studies on 40 and 57 were performed and demonstrated that parent drug was present in tumor 3.0 h post ip (50 mg/Kg) dose.
Yan, Chao,Theodorescu, Dan,Miller, Bettina,Kumar, Amit,Kumar, Vijay,Ross, David,Wempe, Michael F.
supporting information
p. 5815 - 5818
(2016/11/25)

Diversification of edaravone via palladium-catalyzed hydrazine cross-coupling: Applications against protein misfolding and oligomerization of beta-amyloid
N-Aryl derivatives of edaravone were identified as potentially effective small molecule inhibitors of tau and beta-amyloid aggregation in the context of developing disease-modifying therapeutics for Alzheimer's disease (AD). Palladium-catalyzed hydrazine monoarylation protocols were then employed as an expedient means of preparing a focused library of 21 edaravone derivatives featuring varied N-aryl substitution, thereby enabling structure-activity relationship (SAR) studies. On the basis of data obtained from two functional biochemical assays examining the effect of edaravone derivatives on both fibril and oligomer formation, it was determined that derivatives featuring an N-biaryl motif were four-fold more potent than edaravone.
Maclean, Mark A.,Diez-Cecilia, Elena,Lavery, Christopher B.,Reed, Mark A.,Wang, Yanfei,Weaver, Donald F.,Stradiotto, Mark
supporting information
p. 100 - 104
(2015/12/18)

Pyrazole based solid state emissive NLOphores with TICT characteristics: Synthesis, DFT and TDDFT studies
A series of pyrazole based D-π-A derivatives with large stokes shift have been synthesized from 1,3-dipheny-1H-pyrazole-3-carbaldehyde by reacting with a series of active methylenes and characterized by spectroscopic analysis. The synthesized dyes show blue to red solid state emissions in the range of 441-604 nm. All the pyrazole dyes, except dye 2.3.6.4-((1,3-dipheny-1H-pyrazole-4-yl)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, display solid state emission characteristics. Experimental absorption and emission wavelengths measured for all the synthesized dyes are in good agreement with those predicted using the Time-Dependent Density Functional Theory. In this paper, the static first, second hyperpolarizability and its related properties estimated for pyrazole based "push-pull" dyes using B3LYP functional with 6-311G(d) basis sets. We have performed experimental calculation to determine the first hyperpolarizability using solvatochromic shift method. These dyes show high first hyperpolarizability in the range of 39.96-296.35 × 10-30 esu by theoretical method and 35.8-302 × 10-30 esu by solvatochromic shift method.
Lanke, Sandip K.,Sekar, Nagaiyan
p. 62 - 75
(2015/12/18)

The discovery of indole derivatives as novel hepatitis C virus inhibitors
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
p. 147 - 155
(2016/04/20)

Iodine-mediated construction of polyfunctionalized arylazopyrazoles from β-ketoesters or 2-arylpyrazol-3-ones and arylhydrazines
This paper describes step-economic iodine-mediated construction of functionalized arylazopyrazoles in the presence of catalytic AgNO3 starting from simple β-ketoesters and two equivalents of arylhydrazines. This cascade reaction includes in situ α-iodination of β-ketoesters, pyrazol-3-one formation, substitution with a nitrogen nucleophile, and oxidation/aromatization.
Pandit, Rameshwar Prasad,Kim, Sung Hong,Lee, Yong Rok
supporting information
p. 6996 - 7000
(2016/07/30)