36640-56-9

Usage

InChI:InChI=1/C17H16N2O2/c1-21-16-9-7-13(8-10-16)17-14(12-20)11-19(18-17)15-5-3-2-4-6-15/h2-11,20H,12H2,1H3

Upstream product

• 100-63-0 phenylhydrazine 
• 36640-42-3 3-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-4-carboxaldehyde 
• 24310-46-1 4-methoxyacetophenone phenylhydrazone 
• 59-88-1 phenylhydrazine hydrochloride 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 873312-93-7 4-(azidomethyl)-3-(4-methoxyphenyl)-1-phenyl-1H-pyrazole 
• 873312-85-7 4-(chlorophenyl)-3-(4-methoxyphenyl)-1-phenyl-1H-pyrazole 

Relevant academic research and scientific papers

Novel Aryl Substituted Pyrazoles as Small Molecule Inhibitors of Cytochrome P450 CYP121A1: Synthesis and Antimycobacterial Evaluation

Three series of biarylpyrazole imidazole and triazoles are described, which vary in the linker between the biaryl pyrazole and imidazole/triazole group. The imidazole and triazole series with the short -CH2- linker displayed promising antimycobacterial activity, with the imidazole-CH2- series (7) showing low MIC values (6.25-25 μg/mL), which was also influenced by lipophilicity. Extending the linker to -C(O)NH(CH2)2- resulted in a loss of antimycobacterial activity. The binding affinity of the compounds with CYP121A1 was determined by UV-visible optical titrations with KD values of 2.63, 35.6, and 290 μM, respectively, for the tightest binding compounds 7e, 8b, and 13d from their respective series. Both binding affinity assays and docking studies of the CYP121A1 inhibitors suggest type II indirect binding through interstitial water molecules, with key binding residues Thr77, Val78, Val82, Val83, Met86, Ser237, Gln385, and Arg386, comparable with the binding interactions observed with fluconazole and the natural substrate dicyclotyrosine.

Synthesis, pharmacological activities and molecular docking studies of pyrazolyltriazoles as anti-bacterial and anti-inflammatory agents

A series of novel pyrazolyl alcohols (5a-h), pyrazolyl azides (6a-h), and pyrazolyltriazoles (8a-h, 10a-p and 12a-l) were prepared and evaluated for their bioactivity (anti-bacterial and anti-inflammatory) profile. The compound 5c displayed the potent anti-bacterial activity against Micrococcus luteus (MIC 3.9 and MBC 7.81 μg/mL). In vitro anti-inflammatory activity data denoted that compound 8b is effective among the tested compounds against IL-6 (IC50 6.23 μM). Docking analysis of compounds 5f, 8a-b, 8e-f and 8h displayed high binding energies for the compounds 8a-b and 8h towards TNF-α dimer (2AZ5 protein) and IL-6 (1ALU protein). In vivo anti-inflammatory activity of compounds 8b and 8h with respect to LPS induced mice model indicated that compound 8h showed significant reduction in TNF-α.

Unexpected Metal-Free Fluorination and Oxidation at the C-4 Position of Pyrazoles Promoted by Selectfluor

Metal-free electrophilic fluorination, promoted by Selectfluor, of pyrazoles with methylene groups (CH2X), in which XA =A OH, OMe, F, N3, and NHMe at the C-4 position furnished the 4-fluoro-pyrazole products from unexpected C-C bond cleavage, at moderate to good yields. Otherwise, under the same reaction conditions, when XA =A NEt2 or SPr, the oxidation product 4-formyl-pyrazole was obtained.

New 4-fluoroalkyl substituted N-phenylpyrazoles: Synthesis promoted by DAST and multinuclear NMR analysis

This paper reports a synthetic and NMR spectroscopic studies of two new series of 4-fluorinated 1,3,5-substituted 1H-pyrazoles. Firstly, an efficient synthesis of new series of 3-aryl-4-(di)fluoromethyl-1H-1-phenylpyrazoles, where [aryl = Ph, 4-NO2/

Design, synthesis and biological evaluation of (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives as potential BRAFV600E inhibitors

A series of (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives (6a-10d) were designed, synthesized and evaluated as BRAFV600E inhibitors. Biological evaluation assays indicated that compound 10a showed the most potent inhibitory activity against A375, WM266.4 and BRAFV600Ein vitro with IC50 values of 1.36 μM, 0.94 μM and 0.11 μM respectively compared with the positive compound vemurafenib. Furthermore, compound 10a showed highly selective BRAFV600E inhibitory activity in vitro. A docking simulation displayed that compound 10a could tightly bind the crystal structure of BRAFV600E at the active site. 3D-QSAR would provide a guideline to design and optimize more potent and positive BRAFV600E inhibitors based on the (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives skeleton.

Synthesis, molecular modeling and biological evaluation of cinnamic acid derivatives with pyrazole moieties as novel anticancer agents

A series of pyrazole derivatives (1e-30e) has been designed and synthesized, and their biological activities were evaluated for EGFR and HER-2 inhibition and tumor cell antiproliferation. Among the compounds synthesized, compound 30e exhibited excellent enzyme inhibitory activity (IC50 = 0.21 ± 0.05 μM for EGFR and IC50 = 1.08 ± 0.15 μM for HER-2). Compound 30e also showed the most potent antiproliferative activity, which inhibited the growth of MCF-7 and B16-F10 cell lines with IC50 values of 0.30 ± 0.04 and 0.44 ± 0.05 μM, respectively. The molecular docking study was performed to analyze the probable binding models and the 3D-QSAR models were built for the rational design of EGFR/HER-2 inhibitors. Based on the results obtained, compound 30e with potent EGFR and HER-2 inhibitory activity may be a potential anticancer agent. the Partner Organisations 2014.

Pyrazol-4-acetic acid compounds

Pyrazol-4-acetic acid compounds, such as substituted pyrazol-4-acetic acid, its esters, amides, nitriles and their pharamaceutically acceptable salts and method for the preparation of these compounds are disclosed. The novel compounds are useful analgesics, anti-inflammatory, and antipyretics.