77509-93-4

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 13024-90-3 1-(4-chlorophenyl)-3-methyl-2-pyrazolin-5-one 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 20629-92-9 1-(4-chlorophenyl)-3-methyl-3-pyrazolin-5-one 

Downstream Products

• 1084328-18-6 C₁₇H₁₂ClFN₂OS 
• 1084328-17-5 C₁₈H₁₅ClN₂O₂S 
• 1084328-19-7 C₁₈H₁₅ClN₂OS 

Relevant academic research and scientific papers

Discovery of novel triazole-containing pyrazole ester derivatives as potential antibacterial agents

To develop new antibacterial agents, a series of novel triazole-containing pyrazole ester derivatives were designed and synthesized and their biological activities were evaluated as potential topoisomerase II inhibitors. Compound 4d exhibited the most potent antibacterial activity with Minimum inhibitory concentration (MIC) alues of 4 μg/mL, 2 μg/mL, 4 μg/mL, and 0.5 μg/mL against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, and Salmonella gallinarum, respectively. The in vivo enzyme inhibition assay 4d displayed the most potent topoisomerase II (IC50 = 13.5 μg/mL) and topoisomerase IV (IC50 = 24.2 μg/mL) inhibitory activity. Molecular docking was performed to position compound 4d into the topoisomerase II active site to determine the probable binding conformation. In summary, compound 4d may serve as potential topoisomerase II inhibitor.

Design, synthesis and biological evaluation of novel pyrazole sulfonamide derivatives as potential AHAS inhibitors

Acetohydroxy acid synthase (AHAS; EC 2.2.1.6, also referred to as acetolactate synthase, ALS) has been considered as an attractive target for the design of herbicides. In this work, an optimized pyrazole sulfonamide base scaffold was designed and introduced to derive novel potential AHAS inhibitors by introducing a pyrazole ring in flucarbazone. The results of in vivo herbicidal activity evaluation indicates compound 3b has the most potent activity with rape root length inhibition values of 81percent at 100 mg/L, and exhibited the best inhibitory ability against Arabidopsis thaliana AHAS. With molecular docking, compound 3b insert into Arabidopsis thaliana AHAS stably by an H-bond with Arg377 and cation-p interactions with Arg377, Trp574, Tyr579. This study suggests that compound 3b may serve as a potential AHAS inhibitor which can be used as a novel herbicides and provides valuable clues for the further design and optimization of AHAS inhibitors.

Discovery of novel double pyrazole Schiff base derivatives as anti-tobacco mosaic virus (TMV) agents

Many pyrazole derivatives were reported to exhibit highly activity towards tobacco mosaic virus (TMV). In this work, an optimized pyrazole Schiff base scaffold was designed and introduced to derive novel potential TMV inhibitors. Thirty-six compounds were synthesized, characterized by elemental analysis, mass spectra and nuclear magnetic resonance (NMR) spectroscopy and evaluated by biological experiments. The bioassay results showed that some of the synthesized compounds exhibited excellent anti-TMV activities. Especially, 5-chloro-3-methyl-1H-pyrazole contained compound 4j showed ningnanmycin comparable inhibitory activity and can be considered as potential anti-TMV candidate agent. With molecular docking, compound 4j insert into nucleotide sequence (GAAGUU) of OriRNA stably which revealed nucleotide could be a target of these compounds.

Containing substituted 1, 3, 4-thiadiazole sulfide pyrazole amide and pyrazole imine derivatives and preparation method and application

The invention discloses pyrazole amide and pyrazole imine derivatives containing substituted 1, 3, 4-thiadiazole thioether as well as a preparation method and an application of the derivatives. The compounds have the structures as shown in formulae (I) and (II). The preparation method comprises the following steps: by taking substituted hydrazine as an initial raw material, carrying out closed loop, chlorine formylation, oxidation and chloro reaction to obtain pyrazole acyl chloride; carrying out a reaction on 2-amino-5-mercapto-1, 3, 4-thiadiazole and substituted benzyl chloride to obtain 2-amino-5-substituted 1, 3, 4-thiadiazole thioether; and then, carrying out a substitution reaction on 2-amino-5-substituted 1, 3, 4-thiadiazole thioether and substituted pyrazole acyl chloride to obtain the pyrazole amide compound (I) containing substituted 1, 3, 4-thiadiazole thioether; by taking substituted hydrazine as an initial raw material, carrying out closed loop and chlorine formylation to obtain pyrazole aldehyde; carrying out an additive elimination reaction on pyrazole aldehyde and 2-amino-5-mercapto-1, 3, 4-thiadiazole under a backflow condition of anhydrous ethanol to obtain 2-substituted pyrazole imidogen-5-mercapto-1, 3, 4-thiadiazole; and then carrying out a reaction on 2-substituted pyrazole imidogen-5-mercapto-1, 3, 4-thiadiazole and substituted benzyl chloride to generate the pyrazole imine compound (II) containing substituted 1, 3, 4-thiadiazole thioether. The compounds disclosed by the invention have a good inhibiting effect on tobacco mosaic virus and can be used for preparing anti-plant virus drugs.

Design, synthesis and anti-tobacco mosaic virus (TMV) activity of 5-chloro-n-(4-cyano-1-aryl-1H-pyrazol-5-yl)-1-aryl-3-methyl-1H-pyrazole-4-carboxamide derivatives

A series of novel pyrazole amide derivatives 3a-3p which take TMV PC protein as the target has been designed and synthesized by the reactions of 5-chloro-1-aryl-3-methyl-1H-pyrazole-4-carboxylic acids with 5-amino-1-aryl-1H-pyrazole-4-carbonitriles. All the compounds were characterized by 1H-NMR, mass spectroscopy and elemental analysis. Preliminary bioassays indicated that all the compounds acted against the tobacco mosaic virus (TMV) with different in vivo and in vitro modes at 500 μg/mL and were found to possess promising activity. Especially, compound 3p showed the most potent biological activity against tobacco mosaic virus (TMV) compared to ningnanmycin, and a molecular docking study was performed and the binding model revealed that the pyrazole amide moiety was tightly embedded in the binding sites of TMV PC (PDB code: 2OM3).

Chemoselective Synthesis of 5-Alkylamino-1H-pyrazole-4-carbaldehydes by Cesium- and Copper-Mediated Amination

Microwave-assisted synthesis of new 5-alkylamino-pyrazole-4-carbaldehydes was performed efficiently, with yields up to 99 and short reaction times. Nucleophilic substitution of primary alkylamines with activated 5-chloro-1-(2-pyridyl)pyrazole-4-carbaldehyde was mediated by the "cesium effect". The amination of deactivated 1-aryl-5-chloropyrazole-4-carbaldehydes was also assisted by the cesium ion and catalyzed by copper(I). Hereby is described an efficient protocol for the chemoselective synthesis of new 5-alkylaminopyrazole-4-carbaldehydes from 5-chloropyrazole-4-carbaldehydes and primary alkylamines in one step to give products with good to excellent yields and short reaction times. Unexpectedly, under these reaction conditions the corresponding alkylimine formation was not observed.

Design, synthesis and molecular modeling of pyrazole-quinoline-pyridine hybrids as a new class of antimicrobial and anticancer agents

A new series of pyrazole-quinoline-pyridine hybrids were designed based on molecular hybridization technique and synthesized by a base-catalyzed cyclocondensation reaction through one-pot multicomponent reaction. All compounds were tested for in vitro ant

Synthesis and antiviral activities of pyrazole derivatives containing an oxime moiety

Target compounds 4a-n were obtained by the reaction of 1 -substituted phenyl-3-methyl-5-substituted phenylthio-4-pyrazolaldoximes (3) with chloromethylated heterocyclic compounds (CICH2-R3) under reflux conditions in ethanol. Subsequ