52217-38-6

Usage

Heterocyclic compound

Consists of a pyrazole ring and a pyridine ring fused together

Functional group

Contains a carbonitrile group

Aromatic nature

Has a phenyl group in its structure

Use in organic synthesis

Used as a building block or intermediate for the preparation of biologically active molecules and pharmaceutical drugs

Potential applications

May have antimicrobial, anti-inflammatory, or antitumor properties.

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 52217-35-3 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 114362-54-8 5-azido-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 89-25-8 edaravone 
• 100-63-0 phenylhydrazine 
• 947-95-5 5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole 
• 176387-60-3 6-amino-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile 

Downstream Products

• 81933-79-1 ethyl 1-phenyl-3-methylpyrazolo<3,4-b>pyridin-6(7H)-one-5-carboxylate 
• 81933-80-4 1-phenyl-3-methylpyrazolo<3,4-b>pyridin-6(7H)-one-5-carboxylic acid 
• 247576-27-8 6-chloro-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile 
• 283588-75-0 5-(2-imidazolin-2-yl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-6(7H)-thione 
• 283588-73-8 5-(2-imidazolin-2-yl)-6-hydrazino-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine 
• 1610624-67-3 3-methyl-5-((methyl(3-(trifluoromethyl)benzyl)amino)methyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one 
• 1610624-69-5 3,7-dimethyl-1-phenyl-5-((3-(trifluoromethyl)benzylamino)methyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one 
• 1610624-70-8 1-(6-methoxy-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-N-(3-(trifluoromethyl)benzyl)methanamine 
• 1610624-50-4 5-((3,4-dimethylbenzylamino)methyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one 
• 1181245-09-9 C₁₄H₁₄N₄O 
• 1610624-51-5 5-((benzylamino)methyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one 
• 1610624-95-7 tert-butyl ((3,7-dimethyl-6-oxo-1-phenyl-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)carbamate 
• 1610624-53-7 3-(((3-methyl-6-oxo-1-phenyl-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-5-yl)methylamino)methyl)benzonitrile 
• 1610624-96-8 5-(aminomethyl)-3,7-dimethyl-1-phenyl-1,7-dihydro-6H-pyrazolo[3,4-b]pyridin-6-one 

Relevant academic research and scientific papers

Discovery of Novel Pyrazolo[3,4- b] Pyridine Derivatives with Dual Activities of Vascular Remodeling Inhibition and Vasodilation for the Treatment of Pulmonary Arterial Hypertension

Current pulmonary arterial hypertension (PAH) therapeutic strategies mainly focus on vascular relaxation with less emphasis on vascular remodeling, which results in poor prognosis. Hence, dual pathway regulators with vasodilation effect via soluble guanylate cyclase (sGC) stimulation and vascular remodeling regulation effect by AMP-activated protein kinase (AMPK) inhibition provide more advantages and potentialities. Herein, we designed and synthesized a series of novel pyrazolo[3,4-b] pyridine derivatives based on sGC stimulator and AMPK inhibitor scaffolds. In vitro, 2 exhibited moderate vasodilation activity and higher proliferation and migration suppressive effects compared to riociguat. In vivo, 2 significantly decreased right ventricular systolic pressure (RVSP), attenuated pulmonary artery medial thickness (PAMT), and right ventricular hypertrophy (RVH) in hypoxia-induced PAH rat models (i.g.). Given the unique advantages of significant vascular remodeling inhibition and moderate vascular relaxation based on the dual pathway regulation, we proposed 2 as a promising lead for anti-PAH drug discovery.

Discovery of pyrazolopyridones as a novel class of noncovalent DprE1 inhibitor with potent anti-mycobacterial activity

A novel pyrazolopyridone class of inhibitors was identified from whole cell screening against Mycobacterium tuberculosis (Mtb). The series exhibits excellent bactericidality in vitro, resulting in a 4 log reduction in colony forming units following compound exposure. The significant modulation of minimum inhibitory concentration (MIC) against a Mtb strain overexpressing the Rv3790 gene suggested the target of pyrazolopyridones to be decaprenylphosphoryl- β-d-ribose-2′-epimerase (DprE1). Genetic mapping of resistance mutation coupled with potent enzyme inhibition activity confirmed the molecular target. Detailed biochemical characterization revealed the series to be a noncovalent inhibitor of DprE1. Docking studies at the active site suggest that the series can be further diversified to improve the physicochemical properties without compromising the antimycobacterial activity. The pyrazolopyridone class of inhibitors offers an attractive non-nitro lead series targeting the essential and vulnerable DprE1 enzyme for the discovery of novel antimycobacterial agents to treat both drug susceptible and drug resistant strains of Mtb.

Synthesis of newly substituted pyrazoles and substituted pyrazolo[3,4-b]pyridines based on 5-amino-3-methyl-1-phenylpyrazole

The reaction of the aminopyrazole 1 with benzenesulfonyl chloride, arenediazonium salt, chloroacetyl chloride, ethoxy methyleneamlononitrile and with ethyl 2-cyano-3-ethoxyacrylate gave the substituted 3-methyl-1- phenylpyrazole 2-5a,b. Compound 5b was cy