109740-09-2

Basic information

• Product Name: 2-PHENYL-2,5-DIHYDRO-4H-PYRAZOLO[3,4-C]QUINOLIN-4-ONE
• Synonyms: 2-PHENYL-2,5-DIHYDRO-4H-PYRAZOLO[3,4-C]QUINOLIN-4-ONE;2-phenyl-5H-pyrazolo[3,4-c]quinolin-4-one
• CAS NO: 109740-09-2
• Molecular Formula: C₁₆H₁₁N₃O
• Molecular Weight: 261.28
• Mol File: 109740-09-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-PHENYL-2,5-DIHYDRO-4H-PYRAZOLO[3,4-C]QUINOLIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-2,5-DIHYDRO-4H-PYRAZOLO[3,4-C]QUINOLIN-4-ONE(109740-09-2)
• EPA Substance Registry System: 2-PHENYL-2,5-DIHYDRO-4H-PYRAZOLO[3,4-C]QUINOLIN-4-ONE(109740-09-2)

Safety Data

• Hazardous Substances Data: 109740-09-2(Hazardous Substances Data)

Upstream product

• 51079-10-8 ethyl 2-(1H-indol-3-yl)-2-oxoacetate 
• 59-88-1 phenylhydrazine hydrochloride 
• 120-72-9 indole 
• 100-63-0 phenylhydrazine 
• 115316-03-5 ethyl 4-bromo-1-phenyl-1H-pyrazole-3-carboxylate 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 508191-77-3 3-phenylsydnone 
• 41658-03-1 ethyl 3-bromoprop-2-ynoate 

Downstream Products

• 298201-97-5 4-chloro-2-phenyl-2H-pyrazolo[3,4-c]quinoline 
• 298201-68-0 2-phenyl-2H-pyrazolo[3,4-c]quinolin-4-ylamine 

Relevant articles and documents

A novel one-pot synthesis of 2-arylpyrazoloquinolinone derivatives

Two regioisomers of 2-arylpyrazolo[3,4-c]quinolin-4(5H)-ones and 2-arylpyrazolo[4,3-c]quinolin-4(5H)-ones were synthesized by utilizing 3-arylsydnones, ethyl 3-bromopropynoate, and 2-aminophenylboronic acid pinacol ester in presence of catalytic agent Pd(PPh3)4. This efficient one-pot synthesis methodology involved 1,3-dipolar cycloaddition, Suzuki coupling reaction, and intramolecular cyclization three sequence steps.

Novel potent and highly selective human A3 adenosine receptor antagonists belonging to the 4-amido-2-arylpyrazolo[3,4-c]quinoline series: Molecular docking analysis and pharmacological studies

The study of novel 2-arylpyrazolo[3,4-c]quinolin-4-(hetero)arylamides, designed as human (h) A3 adenosine receptor antagonists, is reported. The new derivatives are endowed with nanomolar hA3 receptor affinity and high selectivity versus hA1, hA2A and hA2B receptors. Among the (hetero)aroyl residues introduced on the 4-amino group, the 2-furyl and 4-pyridyl rings turned out to be the most beneficial for hA3 affinity (Ki = 3.4 and 5.0 nM, respectively). An intensive molecular docking study to a rhodopsin-based homology model of the hA3 receptor was carried out to obtain a 'structure-based pharmacophore model' that proved to be helpful for the interpretation of the observed affinities of the new hA3 pyrazoloquinoline antagonists.

New 2-arylpyrazolo[3,4-c]quinoline derivatives as potent and selective human A3 adenosine receptor antagonists. Synthesis, pharmacological evaluation, and ligand-receptor modeling studies

This paper reports the study of some 2-arylpyrazolo[3,4-c]quinolin-4-ones, 4-amines, and 4-amino-substituted derivatives designed as human A3 adenosine receptor (AR) antagonists. Most of the herein reported compounds showed a nanomolar affinity

PYRAZOLO[3,4-c]QUINOLINES, PYRAZOLO[3,4-c]NAPHTHYRIDINES, ANALOGS THEREOF, AND METHODS

Pyrazolo[3,4-c]quinolines, pyrazolo[4,5-c]naphthyridines, and analogs thereof, eg., 6,7,8,9-tetrahydro pyrazolo[3,4-c]quinolines, and, pharmaceutical compositions containing the compounds, intermediates, methods of making these compounds, and methods of use of these compounds as immunomodulators, for inhibiting cytokine biosynthesis in animals and in the therapeutic or prophylactic treatment of diseases by inhibiting cytokine biosynthesis are disclosed.

Tricyclic heteroaromatic systems. Pyrazolo[3,4-c]quinolin-4-ones and pyrazolo[3,4-c]quinoline-1,4-diones: Synthesis and benzodiazepine receptor activity

Some pyrazolo[3,4-c]quinoline-4-ones 1-14 and pyrazolo[3,4-c]-quinoline-1,4-diones 15-17 were prepared and biologically evaluated for their binding at the benzodiazepine receptor (BZR) in rat cortical membranes. The moderate binding activity of 1-5, 7, 9-10, 13 is attributable to the lack of the optional proton acceptor at position-1, while the inactivity of the 1,4-dione derivatives 15-17 is due to the lack of the essential proton acceptor at position-3. These conclusions confirm the validity of our proposed pharmacophoric model.

SYNTHESIS OF 2H-PYRAZOLOQUINOLINE DERIVATIVES BY ONE POT REARRANGEMENT OF PHENYLHYDRAZONES OF 3-ACYLINDOLES

The phenylhydrazones 4a-g of 3-acylindoles led to the 2-phenyl-2H-pyrazoloquinoline derivatives 9a-e and 10a-b.The reaction mechanism proposed involves an acid catalysed 6 ? heteroelektrocyclic reaction and a ring opening to the pyrazole derivative