832715-52-3

Basic information

• Product Name: 1-(4-BroMophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyriMidine
• Synonyms: 1-(4-BroMophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyriMidine;1-(4-bromophenyl)-4-chloropyrazolo[3,4-d]pyrimidine
• CAS NO: 832715-52-3
• Molecular Formula: C₁₁H₆BrClN₄
• Molecular Weight: 309.54914
• Mol File: 832715-52-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 365.5±42.0 °C(Predicted)
• Appearance: /
• Density: 1.81±0.1 g/cm3(Predicted)
• PKA: 1.23±0.30(Predicted)
• CAS DataBase Reference: 1-(4-BroMophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyriMidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-BroMophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyriMidine(832715-52-3)
• EPA Substance Registry System: 1-(4-BroMophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyriMidine(832715-52-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 832715-52-3(Hazardous Substances Data)

Usage

General Description

1-(4-Bromophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine is a chemical compound that belongs to the class of pyrazole derivatives. It is a yellow solid and is insoluble in water. 1-(4-BroMophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyriMidine is used in the pharmaceutical industry for its potential biological activities, such as its ability to act as an inhibitor for certain enzymes. It has also been studied for its potential as an anti-cancer agent, as well as for its use in the treatment of inflammatory and autoimmune diseases. However, further research is needed to fully understand its potential therapeutic applications.

Upstream product

• 864872-05-9 1-(4-bromo-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 
• 5305-40-8 2,6-dichloro-pyrimidine carbaldehyde 
• 106-40-1 4-bromo-aniline 
• 1429924-49-1 5-((2-(4-bromophenyl)hydrazono)methyl)-4,6-dichloropyrimidine 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 1231710-82-9 5-{[2-(4-bromophenyl)hydrazono]methyl}-4,6-dichloropyrimidine 
• 5334-28-1 5-amino-1-(4-bromophenyl)-1H-pyrazole-4-carbonitrile 
• 589-21-9 (4-bromophenyl)hydrazine 

Downstream Products

• 887327-49-3 [1-(4-bromo-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-o-tolyl-amine 
• 940311-36-4 N-{3-[1-(4-bromophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-4-methyl-phenyl}-3-trifluoromethyl-benzamide 

Relevant articles and documents

Design and synthesis of pyrazolo[3,4-d]pyrimidines: Nitric oxide releasing compounds targeting hepatocellular carcinoma

A new series of pyrazolo[3,4-d]pyrimidines tethered with nitric oxide (NO) producing functionality was designed and synthesized. Sulforhodamine B (SRB) protein assay revealed that NO releasing moiety in the synthesized compounds significantly decreased the cell growth more than the des-NO analogues. Compounds 7C and 7G possessing N-para-substituted phenyl group, released the highest NO concentration of 4.6% and 4.7% respectively. Anti-proliferative activity of synthesized compounds on HepG2 cell line identified compounds 7h, 7p, 14a and 14b as the most cytotoxic compounds in the series of IC50?=?3, 5, 3 and 5?μM, respectively, compared to erlotinib as a reference drug (IC50?=?25?μM). Flow cytometry studies revealed that 7?h arrested the cells in G0/G1 phase of cell cycle while 7p arrested the cells in S phase. Moreover, docking study of the synthesized compounds on EGFR (PDB code: 1M17) and cytotoxicity study indicated that N-1 phenyl para substitution, pyrazole C-3 alkyl substitution and tethering the nitrate moiety through butyl group had a significant impact on the activity.

Selective synthesis of 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines

Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5- carboxaldehyde with various hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective and high-yielding manner are presented. For aromatic hydrazines, the reaction is performed in the absence of an external base, which promotes exclusive hydrazone formation. The hydrazones subsequently cyclize at an elevated temperature to form the desired pyrazolo[3,4-d]pyrimidine products. For aliphatic hydrazines, the reaction sequence proceeds as a single step in the presence of an external base.

3-(SUBSTITUTED AMINO)-PYRAZOLO[3,4-d]PYRIMIDINES AS EPHB AND VEGFR2 KINASE INHIBITORS

The invention relates to novel pyrazolo[3,4-d]pyrimidines of the formula in which all of the variables are as defined in the specification, in free form or in salt form, to their preparation, to their use as medicaments and to medicaments comprising them.