890764-10-0

Usage

Structure

Pyrazole derivative with a chlorine-substituted phenyl group at one end and a phenyl group at the other end

Potential applications

Medicinal chemistry, as a building block for synthesizing new pharmaceuticals or as a research tool in biochemical studies

Biological activity

May exhibit biological activity due to its structure and functional groups

Specific properties and uses

Depend on further investigation and testing in the laboratory

Upstream product

• 17196-74-6 (Z)-3-amino-3-phenylacrylonitrile 
• 10449-07-7 (2-chlorophenyl)hydrazine 
• 614-16-4 Benzoylacetonitrile 
• 95-51-2 o-chloroaniline 
• 100-47-0 benzonitrile 

Downstream Products

• 1257533-39-3 N′-[1-(2-chlorophenyl)-4-formyl-3-phenyl-1H-pyrazol-5-yl]-N,N-dimethylmethanimidamide 
• 1400634-59-4 1-(2-chlorophenyl)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 1309921-15-0 4-bromo-N-(1-[2-chlorophenyl]-3-phenyl-1H-pyrazol-5-yl)picolinamide 
• 1309921-06-9 3-cyano-4-(1-naphthyl)-N-(1-[2-chlorophenyl]-3-phenyl-1H-pyrazol-5-yl)benzamide 
• 1309921-05-8 3-cyano-4-(4-fluorophenyl)-N-(1-[2-chlorophenyl]-3-phenyl-1H-pyrazol-5-yl)benzamide 
• 1309921-04-7 3-cyano-4-(3-fluorophenyl)-N-(1-[2-chlorophenyl]-3-phenyl-1H-pyrazol-5-yl)benzamide 
• 1309921-03-6 3-cyano-4-phenyl-N-(1-[2-chlorophenyl]-3-phenyl-1H-pyrazol-5-yl)benzamide 

Relevant academic research and scientific papers

One-pot, telescoped synthesis of N-aryl-5-aminopyrazoles from anilines in environmentally benign conditions

An efficient synthetic approach to synthesize N-aryl-5-aminopyrazoles from anilines via a one-pot, telescoped reaction performed in entirely aqueous conditions has been developed. This protocol provides a rapid, convenient method to prepare N-aryl-5-aminopyrazoles, useful building blocks for the synthesis of several bicyclic nitrogen heterocycles, by avoiding the isolation of the toxic intermediate arylhydrazines and the use of a metallic reductant. The Royal Society of Chemistry 2014.

Substituent effects of N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides on positive allosteric modulation of the metabotropic glutamate-5 receptor in rat cortical astrocytes

CDPPB [3-cyano-N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamide] was recently described as the first centrally active, positive allosteric modulator of rat and human metabotropic glutamate receptor (mGluR) mGluR5 subtype. We explored the structural requirements for potentiation of glutamate-induced calcium release in naturally expressed mGluR5 in cultured rat astrocytes and increasing affinity for the allosteric antagonist binding site by evaluating 50 analogues of CDPPB. In the fluorometric calcium assay, CDPPB exhibited an EC50 value of 77 ± 15 nM in potentiating mGluR 5-mediated responses in cortical astrocytes and a Ki value of 3760 ± 430 nM in displacing [3H]methoxyPEPy binding in membranes of cultured HEK-293 cells expressing rat mGluR5. The structure-activity relationships showed that electronegative aromatic substituents in the para-position of the benzamide moiety of CDPPB increase potency. Both binding and functional activities were further increased with a halogen atom in the ortho-position of the 1-phenyl ring. These effects of substitution do not match those of either aromatic ring of MPEP [2-methyl-6-(phenylethynyl)-pyridine] for the antagonist allosteric binding site. Combination of the optimal substituents and aromatic positions resulted in 4-nitro-N-(1-(2-fluorophenyl)-3-phenyl-1H-pyrazol-5-yl)benzamide (VU-1545) showing Ki = 156 ± 29 nM and EC50 = 9.6 ± 1.9 nM in the binding and functional assays, respectively.