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Usage

Uses

Used in Medicinal Chemistry:
5-AMINO-1-(4-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID is used as a pharmaceutical intermediate for the development of new drugs. Its unique structure and potential pharmacological properties make it a promising candidate for the creation of novel therapeutic agents.
Used in Agrochemicals:
In the agrochemical industry, 5-AMINO-1-(4-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID is utilized as a key intermediate in the synthesis of agrochemicals, contributing to the development of innovative products for crop protection and enhancement of agricultural yields.
Used in Chemical Synthesis:
5-AMINO-1-(4-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID serves as a versatile intermediate in the synthesis of various compounds with related structures and properties. Its unique features make it a valuable building block for the creation of new chemical entities with potential applications in different fields.
Used in Research and Development:
The chemical and biological properties of 5-AMINO-1-(4-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID make it a subject of interest for further research and exploration in various scientific and technological domains. Its potential applications in medicinal chemistry, agrochemicals, and chemical synthesis drive ongoing studies to uncover new uses and optimize its synthesis and properties.

Upstream product

• 371-14-2 4-fluorophenylhydrazine 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 
• 138907-68-3 ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate 

Downstream Products

• 249937-08-4 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbothioic acid S-pyridin-2-yl ester 
• 960249-88-1 (S)-5-amino-1-(4-fluorophenyl)-N-(3,3,3-trifluoro-2-hydroxy-2-(hydroxymethyl)propyl)-1H-pyrazole-4-carboxamide 
• 960249-80-3 5-amino-N-{2-[(ethylamino)methyl]-3,3,3-trifluoro-2-hydroxypropyl}-1-(4-fluorophenyl)-1H-pyrazole-4-carboxamide 

Relevant academic research and scientific papers

Synthesis of pyrazole-carboxamides and pyrazole-carboxylic acids derivatives: Simple methods to access powerful building blocks

Hybrid systems containing pyrazole moiety show a wide spectrum of biological activities. To access novel hybrids with pyrazole ring, in this work we synthesized twenty pyrazole-carboxylic acids and twenty pyrazole-carboxamides, using simple synthetic methods, to be used as building blocks in the development of new structures.

Novel Pyrazolo[3,4- d]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation

Plant pathogenic fungi seriously threaten agricultural production. There is an urgent need to develop novel fungicides with low toxicity and high efficiency. In this study, we designed and synthesized 44 pyrazolo[3,4-d]pyrimidin-4-one derivatives and evaluated them for their fungicidal activities. The bioassay data revealed that most of the target compounds possessed moderate to high in vitro antifungal activities. Especially compound g22 exhibited remarkable antifungal activity against Sclerotinia sclerotiorum with an EC50 value of 1.25 mg/L, close to that of commercial fungicide boscalid (EC50 = 0.96 mg/L) and fluopyram (EC50 = 1.91 mg/L). Moreover, compound g22 possessed prominent protective activity against S. sclerotiorum in vivo for 24 h (95.23%) and 48 h (93.78%), comparable to positive control boscalid (24 h (96.63%); 48 h (93.23%)). Subsequent studies indicated that compound g22 may impede the growth and reproduction of S. sclerotiorum by affecting the morphology of mycelium, destroying cell membrane integrity, and increasing cell membrane permeability. In addition, the application of compound g22 did not injure the growth or reproduction of Italian bees. This study revealed that compound g22 is expected to be developed for efficient and safe agricultural fungicides.

Discovery of novel multi-substituted benzo-indole pyrazole schiff base derivatives with antibacterial activity targeting DNA gyrase

The design and synthesis of novel multi-substituted benzo-indole pyrazole Schiff base derivatives of potent DNA gyrase inhibitory activity were the main aims of this study. All the novel synthesized compounds were examined for their antibacterial activities against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, and Salmonella. In addition, we selected 20 compounds for the in vitro antibacterial activities assay of 6 drug-resistant bacteria strains. The result revealed compound 8I-w exhibited excellent antibacterial activity against 4 drug-resistant E. coli bacteria strains with IC50 values of 7.0, 17.0, 13.5, and 1.0 μM, respectively. In vitro enzyme inhibitory assay showed that compound 8I-w displayed potent inhibition against DNA gyrase with IC50 values of 0.10 μM. The molecular docking model indicated that compounds 8I-w can bind well to the DNA gyrase by interacting with various amino acid residues. This study demonstrated that the compound 8I-w can act as the most potent DNA gyrase inhibitor in the reported series of compounds and provide valuable information for the commercial DNA gyrase inhibiting bactericides.

Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity

The identification of novel Topoisomerase II (Topo II) inhibitors is one of the most attractive directions in the field of bactericide research and development. In our ongoing efforts to pursue the class of inhibitors, six series of 70 novel coumarin-pyrazole carboxamide derivatives were designed and synthesized. As a result of the evaluation against four destructive bacteria, including Staphylococcus aureus, Listeria monocytogenes, Escherichia coli and Salmonella. Compound 8III-k (MIC = 0.25 mg/L) showed considerable inhibitory activity than ciprofloxacin (MIC = 0.5 mg/L) against Escherichia coli and 8V-c (MIC = 0.05 mg/L) exhibited excellent antibacterial activity than ciprofloxacin (MIC = 0.25 mg/L) against Salmonella. The selected compounds (8III-k, 8V-c and 8V-k) exhibit potent inhibition against Topo II and Topo IV with IC50 values (9.4–25 mg/L). Molecular docking model showed that the compounds 8V-c and 8V-k can bind well to the target by interacting with amino acid residues. It will provide some valuable information for the commercial Topo II inhibiting bactericides.

SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS NADPH OXIDASE INHIBITORS

The present application relates to substituted fused heteroaryl and heterocyclic compounds, useful as nicotinamide adenine dinucleotide phosphate oxidase inhibitors (NADPH oxidase inhibitors), processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by NADPH oxidase. (Formula I)

Novel selective glucocorticoid receptor agonists (SEGRAs) with a covalent warhead for long-lasting inhibition

The synthesis and in vitro properties of six analogues of the selective glucocorticoid receptor (GR) agonist GSK866, bearing a warhead for covalent linkage to the glucocorticoid receptor, is described.

5-Amino-pyrazoles as potent and selective p38α inhibitors

The synthesis and structure-activity relationships (SAR) of p38α MAP kinase inhibitors based on a 5-amino-pyrazole scaffold are described. These studies led to the identification of compound 2j as a potent and selective inhibitor of p38α MAP kinase with excellent cellular potency toward the inhibition of TNFα production. Compound 2j was highly efficacious in vivo in inhibiting TNFα production in an acute murine model of TNFα production. X-ray co-crystallography of a 5-amino-pyrazole analog 2f bound to unphosphorylated p38α is also disclosed.

2-(HETERO-)ARYL,4-CARBONYL SUBSTITUTED PYRAZOLE DERIVATIVES AS INHIBITORS OF P38 MITOGEN-ACTIVATED PROTEIN KINASE

Compounds of formula (I) are inhibitors of p38 MAP kinase activity, and are useful in the treatment of, inter alia, inflammatory and autoimmune disease wherein Ring A is aryl, heteroaryl or heterocyclyl of 5-13 atoms; Ring B is optionally substituted aryl or heteroaryl of 5-13 atoms; Z is (a) a radical of formula -(CH2)z-X1-L1-Y- NHCHR1R2 or (b) a radical of formula -(CH2)z-Y1-L1-R wherein R1R2CHNH- and R are respectively N- and C-linked amino acid or amino acid ester groups as defined in the description, and -Y-L1-X1-(CH2)z- and -L1-Y1-(CH2)z- are linker radicals as defined in the description; R7 is hydrogen or -C(=O)R' where R' is hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl or (C1-C6)haloalkyl; R8 is hydrogen or (C1C6)alkyl; R9 is hydrogen, halogen, hydroxyl, (C1-C6)alkoxy, (C1-C6)alkyl; R18 is hydrogen, halogen, hydroxyl, (C1C6)alkoxy (C1-C6)alkyl, - NRaRb where Ra and Rb are hydrogen or (C1-C6)alkyl, or optionally substituted aryl, heteroaryl or heterocyclyl or Ra and Rb when taken together with the nitrogen to which they are attached form a cyclic amino group of up to 6 ring atoms; R19 is hydrogen, halogen, (C1C6)alkoxy, or (C1C6)alkyl.

PYRAZOLE DERIVATIVES AS NON-STEROIDAL GLUCOCORTICOID RECEPTOR LIGANDS

The present invention provides compounds of formula (I), a process for their preparation, to pharmaceutical compositions comprising the compounds and the preparation of said compositions, to intermediates, and to use of the compounds for the manufacture of a medicament for therapeutic treatment, particularly for the treatment of inflammation.

NOVEL COMPOUNDS

The present invention provides compounds of formula (I), a process for their preparation, to pharmaceutical compositions comprising the compounds and the preparation of said compositions, to intermediates and to use of the compounds for the manufacture of