52217-35-3

Upstream product

• 58668-41-0 N'-(4-formyl-5-methyl-2-phenyl-2H-pyrazol-3-yl)-N,N-dimethyl-formamidine 
• 1131-18-6 1-Phenyl-3-methyl-5-aminopyrazole 
• 53106-26-6 N-(5-methyl-2-phenyl-2H-pyrazol-3-yl)-formamide 
• 2590-03-6 N-(3-methyl-1-phenyl-1H-pyrazol-5-yl)acetamide 
• 100-63-0 phenylhydrazine 
• 89-25-8 edaravone 
• 68-12-2 N,N-dimethyl-formamide 
• 64664-15-9 N-(3-methyl-1-phenyl-1H-pyrazol-5-yl)benzamide 
• 1131-17-5 5-chloro-3-methyl-1-phenyl-1H-pyrazole 
• 947-95-5 5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole 
• 114362-54-8 5-azido-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 

Downstream Products

• 53106-31-3 5-amino-3-methyl-1-phenyl-4-<(phenylimino)methyl>pyrazole 
• 81933-79-1 ethyl 1-phenyl-3-methylpyrazolo<3,4-b>pyridin-6(7H)-one-5-carboxylate 
• 98157-52-9 3-methyl-5-nitro-1-phenyl-1H-pyrazolo[3,4-b]pyridine 
• 183736-36-9 6-amino-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 176387-60-3 6-amino-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile 
• 192003-94-4 3-methyl-1-phenyl-6-(pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine 
• 907-55-1 3,5-dimethyl-1,7-diphenyl-1,7-dihydro-dipyrazolo[3,4-b;4',3'-e]pyridine 
• 52217-37-5 1-(3,6-dimethyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-il)etanone 
• 201539-13-1 [Ni(C₂₄H₂₄N₈)] 

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.

Na2S-promoted reduction of azides in water: Synthesis of pyrazolopyridines in one pot and evaluation of antimicrobial activity

Reduction of various azides using Na2S has been accomplished in water, and, in situ, the resulting amines on reaction with various ketones lead to pyrazolo[3,4-b]pyridines in one pot. Thus, a number of new trifluoromethyl-substituted pyrazolo[3,4-b]pyridine compounds have been prepared and screened for antimicrobial activity against different Gram-positive and Gram-negative strains. A good number of compounds, 4a, 4b, 4d, 4f, 4i, 4k, 4l, 4m, 4r and 4s, were found to possess promising activity. Notably, Na2S on hydrolysis in water generates H2S and NaOH, which facilitate the reduction of azides followed by intramolecular cyclization leading to the title compounds. To the best of our knowledge, this is the first report of the synthesis of the title compounds in aqueous medium in a one-pot reaction.

Synthesis of New Heterocycles from Reactions of 1-Phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonyl Azides

Two individual examples of pyrazolo[3,4-b]pyridine-5-carbonyl azides and hydrazides were reacted with various nucleophilic reagents. Different unexpected behaviors was observed. NMR, IR, mass spectra together with elemental analyses and X-ray structure analyses, were used to prove the structure of the obtained products.

Synthesis of novel pyrazole derivatives using organophosphorus, stibine, and arsine reagents and their antitumor activities

The reactions of 5-azido-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (azidopyrazole) with several classes of organophosphorus reagents: phosphonium ylides, Wittig-Horner reagents, dialkylphosphonates, trialkylphosphites, tris(dialkylamino)phosphanes, triphenylstibane, triphenylarsane, and Lawesson's reagent are reported. Structural reasoning for the new products was based on compatible analytical and spectral data. The cytotoxic activity of most of the new products was evaluated against human breast carcinoma cell line (MCF7) and human hepatocellular carcinoma cell line(HepG2). Certain tested compounds showed promising results.

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 and antibacterial activity of some novel pyrazolopyridine derivatives

Eight pyrazolo[3,4-b]pyridine derivatives have been synthesized by Friedlaender condensation of 5-aminopyrazole-4-carbaldehyde with active methylene compounds in basic medium. These compounds have been screened for their antibacterial activity against two Gram-negative and two Gram-positive bacterium. Pyrazolopyridines having the carboxamide group at the 5-position showed moderate to good activity against P. aeruginosa, E. coli, S. pneumoniae, and B. cereus.

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

Design, synthesis, and pharmacological profile of novel fused pyrazolo[4,3-d]pyridine and pyrazolo[3,4-b][1,8]naphthyridine isosteres: A new class of potent and selective acetylcholinesterase inhibitors

A new family of tacrine (THA) analogues (7-9, 12), containing the azaheterocyclic pyrazolo-[4,3-d]pyridine or pyrazolo[3,4-b] [1,8]naphthyridine systems as isosteres of the quinoline ring of THA, has been synthesized. The compounds were tested in rat brai

Reaction of 5-amino-4-formyl-3-methyl(or phenyl)-1-phenyl- 1H-pyrazoles with active methylene compounds: Synthesis of fused heterocyclic rings

A convenient one-pot synthesis of fused heterocyclic ring systems, pyrazolo[3',4':5,6]pyrido[2,3-d]pyrimidines 3a-d, dipyrazolopyridines 4a-b, pyrazolo[3,4-]quinolines 5a-b and 6a-b and pyrazolo[3,4-]pyridines 7a-b, has been achieved by condensation of 5-amino-4-formyl-3-methyl(or phenyl)-1-phenyl-1H-pyrazoles 2a-b with 1,3-diaryl-4,6-dioxo-2-thioxo-hexahydropyrimidines, 3-methyl-1-phenyl-1H-2-pyrazolin-5-one, dimedone, cyclohexanone and 3-acetylpyridine, respectively.

A facile synthesis of pyrazolo[3,4-b]pyridines

Pyrazolo[3,4-b]pyridines (4) and (5) have been obtained by the condensation of 3-(alkyl/aryl)-5-amino-1-phenyl-1H-pyrazole-4-carboxaldehydes (3) with active methylene compounds viz: diethyl malonate and malononitrile.