- Design, synthesis, and fungicidal activity of novel 1,3,4-oxadiazole derivatives
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Employing the intermediate derivatization method (IDM), twenty novel 1,3,4-oxadiazole derivatives containing arylpyrazoloxyl moiety were designed and synthesized. The structures of the title compounds were identified by 1H NMR, 13C NMR, MS and elemental analyses, compound 4 was further identified by single-crystal X-ray diffraction. Antifungal activities against rice sheath blight (RSB) and sorghum anthracnose (SA) were evaluated by the mycelium linear growth rate method. Compounds 4, 16 and 20 displayed significant activities against RSB (EC50 = 0.88 mg/L, 0.91 mg/L and 0.85 mg/L, respectively), higher than the reference tebuconazole; While compound 3 exhibited higher activity against SA (EC50 = 1.03 mg/L), equal to commercial pyraclostrobin (EC50 = 1.06 mg/L). The study showed that compound 20 is a promising fungicide for further development.
- Yu, Fuqiang,Guan, Aiying,Li, Mengru,Hu, Lan,Li, Xiaowu
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- Design, Synthesis, and Structure-Activity Relationship of New Arylpyrazole Pyrimidine Ether Derivatives as Fungicides
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To explore a novel fungicide effectively against cucumber downy mildew (CDM), a series of new arylpyrazole containing pyrimidine ether derivatives were designed and synthesized by employing the intermediate derivatization method (IDM). The structures of synthesized compounds were identified by 1H NMR, 13C NMR, elemental analyses, MS, and X-ray diffraction. Bioassays demonstrated that some of the title compounds exhibited excellent fungicidal activities against CDM. Especially, compound 7 (EC50 = 1.22 mg/L) displayed significantly higher bioactivity than that of commercial fungicides diflumetorim and flumorph and nearly equal effect to that of cyazofamid. The relationship between the structure and fungicidal activity of the synthesized compounds was discussed as well. The study showed that compound 7 was a promising fungicide candidate for further development.
- Zhang, Pengfei,Guan, Aiying,Xia, Xiaoli,Sun, Xufeng,Wei, Siyuan,Yang, Jinlong,Wang, Junfeng,Li, Zhinian,Lan, Jie,Liu, Changling
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- Preparation method of 1-(4-halophenyl)-pyrazolidine-3-ketone
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The invention relates to the field of pesticides, and discloses a preparation method of 1-(4-halogen phenyl)-pyrazolidine-3-ketone, which comprises the following steps: 1) in the presence of an organic solution, carrying out addition reaction on p-halogen aniline and acrylic acid or acrylic ester to obtain an addition reaction product; 2) carrying out nitration reaction on the addition reaction product and a nitration reagent to obtain a nitration product; 3) carrying out hydrogenation reduction on the nitrous acid product in the presence of a hydrogenation catalyst to obtain a reduction product; and 4) removing the hydrogenation catalyst in the reduction product, and carrying out ring closing reaction in the presence of alkali to obtain the 1-(4-halogen phenyl)-pyrazolidine-3-ketone. According to the method, p-chlorophenylhydrazine does not need to be used, and the method is environmentally friendly, easy to operate, high in yield and especially suitable for industrial production.
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- Preparation method of 1-(4-chlorphenyl)-2H-pyrazoline-3-ketone
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The invention relates to a preparation method of 1-(4-chlorphenyl)-2H-pyrazoline-3-ketone, an intermediate reacts with hydrogen peroxide under the action of alkali and a catalyst to generate the 1-(4-chlorphenyl)-2H-pyrazoline-3-ketone, and the structural formula of the intermediate is that the feeding molar ratio of the intermediate to the catalyst is 1: (0.0001-0.001). The preparation method of the 1-(4-chlorphenyl)-2H-pyrazoline-3-ketone has the advantages of simplicity in operation, low catalyst dosage, few three wastes, high efficiency and high yield, and is suitable for industrial production.
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Paragraph 0045-0058
(2022/03/27)
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- COMPOUND HAVING BET INHIBITORY ACTIVITY AND PREPARATION METHOD AND USE THEREFOR
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The invention relates to the field of pharmaceutical chemistry. Specifically, the present invention relates to a series of BET (bromodomain and extra-terminal domain) inhibitors having a novel structure, particularly inhibitors targeting BRD4 (Bromodomain-containing protein 4), and a preparation method and use therefor. The structure thereof is shown in the following general formula (I). Said compounds or a stereoisomer, racemate, geometric isomer, tautomer, prodrug, hydrate, solvate, or crystal form thereof, or a pharmaceutically acceptable salt thereof, and the pharmaceutical compsosition thereof can be used for the treatment and/or prevention of related diseases mediated by bromodomain proteins.
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Paragraph 0196-0197
(2020/12/22)
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- A convenient one-pot synthesis of 1-aryl-substituted 4-iodopyrazol-3-ols via aromatisation and oxidative iodination reactions
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A convenient and economical one-pot synthesis of a series of new 1-aryl-substituted 4-iodopyrazole-3-ols from easily available pyrazolidin- 3-ones in the presence of sodium iodide, 30% solution of hydrogen peroxide and a catalytic amount of sulfuric acid in dichloromethane via aromatisation and oxidative iodination reactions are described. This protocol has the advantages of high atom economy, costeffectiveness, short reaction time and environmental friendliness.
- Liu, Jingjing,Yang, Shanguang,Dong, Ruimei,Jin, Zhudan,Wang, Mingliang
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- METHOD FOR PRODUCING PYRAZOLE COMPOUND
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A method for producing a pyrazole compound represented by formula (1): (wherein R1 represents an optionally substituted C1-12 alkyl group, an optionally substituted C3-12 cycloalkyl group, an optionally substituted C6-16 aryl group, or an optionally substituted pyridyl group, R2 and R3 each independently represent a hydrogen atom, a halogen atom, a C1-3 alkyl group, or a C1-3 haloalkyl group), said method including a step in which a pyrazolidine compound represented by formula (2): (wherein R1, R2, and R3 are as defined above) is reacted with a nitrite in the presence of an acid, allows a pyrazole compound to be produced industrially.
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Paragraph 0036; 0040; 0042; 0044; 0045
(2017/01/26)
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- A process for synthesizing pyraclostrobin
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The invention concretely relates to a synthetic technology for pyraclostrobin. The synthetic technology comprises: firstly performing cyclization to obtain 1-(4-chlorophenyl)-pyrazol-3-one, oxidizing the pyrazol ring under the effect of an oxidant to generate 1-(4-chlorophenyl)-3-hydroxypyrazole, then using 2-nitrobenzyl bromide to performing etherification to generate 1-(4-chlorophenyl)-3-[2-(nitrophenyl)methoxy]-1H-pyrazole, then using a reducing agent to perform nitro reducing, so as to generate N-hydroxyl-2-[N'-(4-chlorophenyl)pyrazol-3'-yloxymethyl]aniline, then using ClCO2CH3 to perform N-acylation reaction to generate methyl N-hydroxyl-N-2-{[N'-(4-chlorophenyl)pyrazol-3'-yloxymethyl]phenyl}formate, and finally performing hydroxyl methylation under an alkaline condition to generate pyraclostrobin. The technology enables all operations in the pyraclostrobin preparation process to be relatively controllable, helps to improve the stability of the preparation process and improve the product yield, successfully employs low-cost reagents and substantially reduces production cost, and also the employed reagents are relatively small in toxicity, is relatively beneficial for environment protection, and has no corrosivity on plastic pipes, so that the production safety is improved.
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Paragraph 0048-0051
(2017/03/08)
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- Synthesis, fungicidal activity, structure-activity relationship and density functional theory studies of novel oxime ether derivatives containing 1-aryl-3-oxypyrazoles
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A series of 16 oxime ether derivatives containing 1-aryl-3-oxypyrazoles were synthesised, and the structure of one of them, (E)-methyl 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate was determined by X-ray diffraction crystallography. Preliminary bioassays indicated that some of these compounds exhibited very good fungicidal activities against Rhizoctonia solani, especially the ester 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate, which displayed greater activity than control compound pyraclostrobin at a dosage of 0.1 μg mL-1. The relationship between structure and fungicidal activity was discussed. Density functional theory studies of the 3-methyl heterocyclic ester and the 4-chorophenyl heterocyclic N-methylamide were carried out and the results discussed in terms of the wide difference in fungicidal activity shown by each compound.
- Lv, Kunzhi,Liu, Yuanyuan,Li, Yi,Xu, Guanghui,Pan, Xuechun,Li, Fangshi,Chen, Kai,Huang, Bin,Yang, Yaping
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p. 594 - 600
(2015/11/27)
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- DMF-catalyzed direct and regioselective C-H functionalization: Electrophilic/nucleophilic 4-halogenation of 3-oxypyrazoles
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A novel, straightforward, and highly regioselective 4-chlorination of 3-oxypyrazole derivatives in boiling thionyl chloride (SOCl2) in the presence of catalytic N,N-dimethylformamide (DMF) has been developed. This reaction likely proceeds through a DMF-catalyzed electrophilic/nucleophilic chlorination mechanism and involves electrophilic attack by SOCl2 and nucleophilic substitution by Cl- as the key steps. Based on this mechanism, the corresponding 4-bromination and 4-iodination of 3-oxypyrazoles have also been achieved in good yield by adding Br- and I -, respectively, to the reaction system. This halogenation method enables quick access to many original 4-halo-3-oxypyrazole series. A novel DMF-catalyzed electrophilic/nucleophilic 4-halogenation of 3-oxypyrazole derivatives has been developed. This halogenation procedure provides quick access to many novel 4-halo-3-oxypyrazole series.
- Liu, Yuanyuan,He, Guangke,Chen, Kai,Jin, Yin,Li, Yufeng,Zhu, Hongjun
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supporting information; experimental part
p. 5323 - 5330
(2011/11/13)
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- Synthesis of site-heterologous haptens for high-affinity anti-pyraclostrobin antibody generation
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The design and synthesis of functional chemical derivatives of small organic molecules is usually a key step for the intricate production of a variety of bioconjugates. In this respect, the derivatization site at which the spacer arm is introduced in immunizing conjugates constitutes a highly critical parameter for the generation of high-affinity and selective antibodies. However, due to the usual complexity of the required synthetic procedures, the appropriate comparison of alternative tethering positions has often been neglected. In the present study, meticulous strategies were followed to prepare synthetic derivatives of pyraclostrobin with the same linkers located at diverse rationally-chosen sites. Activity appraisal of antibodies and bioconjugates was carried out by bidimensional competitive direct and indirect immunoassays, and a superior performance of two of the three synthesized haptens was found. Finally, a detailed analysis of the conformations of the target molecule and the synthesized haptens in aqueous solution was done using computer assisted molecular modeling techniques. This study suggested that the lower titers and affinities of one set of antibodies are most probably due to conformational effects of the spacer arm in the immunizing bioconjugate. The Royal Society of Chemistry 2011.
- Mercader, Josep V.,Agullo, Consuelo,Abad-Somovilla, Antonio,Abad-Fuentes, Antonio
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supporting information; experimental part
p. 1443 - 1453
(2011/04/22)
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- Synthesis, crystal structure and fungicidal activities of new type oxazolidinone-based strobilurin analogues
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A series of oxazolidinone-based strobilurin analogues were efficiently synthesized by the reaction of 3-(2-bromomethylphenyl) oxazolidin-2-one with 1-substituted phenyl-2H-pyrazolin-3-one. Their structures were confirmed and characterized by 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy. In addition, the crystal structure of the target compound 3-(2-((1-phenyl-2H-pyrazol-3-yloxy)methyl)phenyl) oxazolidin-2-one was determined by single crystal X-ray diffraction. The bioassay results of these compounds indicated that some of the oxazolidin-2-one derivatives containing N-substituted phenyl 2H-pyrazol ring exhibited potential in vivo fungicidal activities against M. grisea at the dosage of 1 g L-1.
- Li, Yuhao,Liu, Rui,Yan, Zhangwei,Zhang, Xiangning,Zhu, Hongjun
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p. 3341 - 3347
(2012/05/05)
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- Process for producing N-substituted 3-hydroxypyrazoles
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N-substituted 3-hydroxypyrazoles of the formula I STR1 where R1 is unsubstituted or substituted alkyl, aryl or heteroaryl and R2, R3 is hydrogen, cyano, halogen or unsubstituted or substituted alkyl, aryl or heteroaryl, are prepared by oxidation of a corresponding pyrazolidin-3-one with atmospheric oxygen in the presence of a metal salt in an essentially pH-neutral medium.
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