2924-16-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluorophenylhydrazine hydrochloride is used as a synthetic intermediate for the development of compounds that target pro-inflammatory cytokine mediated diseases. Its application is particularly relevant in the treatment and prevention of conditions associated with p38 activity mediated inflammation.
Used in Research and Development:
In the field of research and development, 3-Fluorophenylhydrazine hydrochloride is utilized for the synthesis of novel compounds with potential therapeutic applications, contributing to the advancement of medical treatments for various inflammatory conditions.

InChI:InChI=1/C6H7FN2.ClH/c7-5-2-1-3-6(4-5)9-8;/h1-4,9H,8H2;1H

Upstream product

• 372-19-0 meta-fluoroaniline 
• 658-27-5 m-fluorophenylhydrazine 
• 1121-86-4 1-Fluoro-3-iodobenzene 

Downstream Products

• 150016-46-9 3-<1-(3-fluorophenylhydrazono)-D-erythro-2,3,4-trihydroxybutyl>quinoxalin-2(1H)-one 
• 188180-95-2 2-(3-Fluoro-phenyl)-3-oxo-3,5-dihydro-2H-pyridazino[4,3-b]indole-4-carboxylic acid ethyl ester 
• 204511-49-9 2-(3-Fluoro-phenyl)-2,5-dihydro-pyrazolo[3,4-c]quinolin-4-one 
• 287099-32-5 ethyl 7-chloro-3-(3-fluorophenyl)-5-methyl-4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-carboxylate 
• 346441-17-6 1-(3-fluorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 6463-46-3 1-(3-fluoro-phenyl)-4,5-dihydro-1H-pyrazol-3-ylamine 
• 3296-03-5 3-fluorophenylazide 
• 51516-71-3 5-amino-1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile 
• 1060664-16-5 4-(5-(4-(dimethylamino)phenyl)-1-(3-fluorophenyl)-4,5-dihydro-1H-pyrazol-3-yl)benzonitrile 
• 1060663-84-4 (+/-)-3-(4-Cyanophenyl)-1-(3-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole 
• 138939-19-2 1-(3-fluorophenyl)-3,5-diphenyl-4,5-dihydro-1H-pyrazole 
• 912963-99-6 adamantane-1-carboxylic acid N'-(3-fluorophenyl)hydrazide 
• 138907-70-7 ethyl 5-amino-1-(3-fluorophenyl)-1H-pyrazole-4-carboxylate 
• 220000-31-7 ethyl 2-benzoylamino-3-[(3-fluorophenyl)hydrazono]propanoate 

Relevant academic research and scientific papers

Design, Synthesis, and Antifungal Activity of 2,6-Dimethyl-4-aminopyrimidine Hydrazones as PDHc-E1 Inhibitors with a Novel Binding Mode

A series of novel 2,6-dimethyl-4-aminopyrimidine hydrazones 5 were rationally designed and synthesized as pyruvate dehydrogenase complex E1 (PDHc-E1) inhibitors. Compounds 5 strongly inhibited Escherichia coli (E. coli) PDHc-E1 (IC50 values 0.94-15.80 μM). As revealed by molecular docking, site-directed mutagenesis, enzymatic, and inhibition kinetic analyses, compounds 5 competitively inhibited PDHc-E1 and bound in a "straight"pattern at the E. coli PDHc-E1 active site, which is a new binding mode. In in vitro antifungal assays, most compounds 5 at 50 μg/mL showed more than 80% inhibition against the mycelial growth of six tested phytopathogenic fungi, including Botrytis cinerea, Monilia fructigena, Colletotrichum gloeosporioides, andBotryosphaeria dothidea. Notably, 5f and 5i were 1.8-380 fold more potent against M. fructigena than the commercial fungicides captan and chlorothalonil. In vivo, 5f and 5i controlled the growth of M. fructigena comparably to the commercial fungicide tebuconazole. Thus, 5f and 5i have potential commercial value for the control of peach brown rot caused by M. fructigena.

Substituted indole urea derivative, synthetic method and application thereof

The invention discloses a substituted indole urea derivative, a synthesis method and application thereof. The structure is shown as a formula I. In the formula, the definition of each substituent group is described in the specification and claims. The compound disclosed by the invention can be used as a cGAS-STING pathway targeting inhibitor and is used for treating inflammatory diseases and autoimmune diseases.

Design, synthesis and biological evaluation of glutamic acid derivatives as anti-oxidant and anti-inflammatory agents

A series of glutamic acid derivatives was synthesized and evaluated for their antioxidant activity and stability. We found several potent and stable glutamic acid derivatives. Among them, compound 12b exhibited good in vitro activity, chemical stability and cytotoxicity. A prototype compound 12b showed an anti-inflammatory effect in LPS-stimulated RAW 264.7 cell lines and in a zebrafish model.

Synthesis of Aryl Hydrazines via CuI/BMPO Catalyzed Cross-Coupling of Aryl Halides with Hydrazine Hydrate in Water

The N,N’-bis(2,6-dimethylphenyl)oxalamide was discovered as a powerful ligand for Cu-catalyzed cross-coupling of aryl halides with hydrazine hydrate, leading to the formation of a variety of aryl hydrazines at 80 oC in water under the assistance of K3PO4 and 4 mol% cetyltrimethylammonium bromide from aryl bromides and aryl iodides. Good to excellent yields were observed in most cases.

Preparation method for 3-fluorophenylhydrazine hydrochloride

The invention relates to a preparation method for 3-fluorophenylhydrazine hydrochloride. The preparation method comprises the following steps: diazotization, reduction, purification and salt formation. During diazotization and reduction, concentrated hydrochloric acid enables a reaction solution to maintain highly acidic, so smooth and complete reaction is guaranteed. In the step of reduction, zinc dust-concentrated hydrochloric acid is used as a reducing agent to replace sodium hyposulfite, sodium bisulfate, stannous chloride-hydrochloric acid, etc., and the zinc dust-concentrated hydrochloric acid is good in reducing property and high in yield, shortens reaction time, enables impurities like zinc hydroxide produced after the reaction to be easy to remove and allows produced 3-fluorophenylhydrazine hydrochloride to be low in impurity content and high in purity. In the step of salt formation, acetone is used for leaching, so product purity is improved and product appearance is guaranteed. The preparation method is stable and reliable in process and easy to operate; and produced 3-fluorophenylhydrazine hydrochloride is high in purity (no less than 99% according to the results of content measurement via high performance liquid chromatography), has a yield of no less than 39% and completely meets market demands for 3-fluorophenylhydrazine hydrochloride.

Synthesis, crystal structure and fungicidal activities of new type oxazolidinone-based strobilurin analogues

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.

New Heterocyclic compounds for therapeutic use

A class of compounds particularly diaryl pyrazole of general formulas 1 and 2 where R and R′ represents alkyl, hydrogen, halogens, haloalkyl, cyano, nitro, formyl, carboxyl, alkoxycarbonyl, carboxyalkyl, alkoxycarbonylalkyl, hydroxyalkyl, alkylthio, alkylsulfinyl, alkylsulphonyl, N- alkylsulfamyl, N-arylsulfamyl, cyanoamido, amino, amidino, N-monoalkylamido, N-monoarylamido, N,N-dialkylamido, N-alkyl-N-arylamido, N, N-dialkylsulfamyl with the alkyl, or alkyl part of each such group containing 1-3 carbon atoms or mixtures thereof optionally their salts when they exist, and preparation thereof. The compounds of the present invention are antiinflammatory, antipyretic, antirheumatic, antiosteoarthritic agents with antibacterial activity. The particular class of compounds is given below (Formula 1 and Formula 2).

Lipoxygenase Inhibitors, III: Synthesis of Tetrahydrobenzazepinone Phenylhydrazones

Tetrahydro-2H-benzazepin-2-ones as starting substances are synthesized by Beckmann rearrangement or Schmidt reaction.The tetrahydrobenzazepinones are transformed into the thiones, thiolactim ethers and phenylhydrazones.The compounds are tested as inhibitors of soja lipoxygenase.