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

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 characterized by its yellow solid appearance and its insolubility in water. 1-(4-BroMophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyriMidine is of interest in the pharmaceutical industry due to its potential biological activities, which include its ability to inhibit certain enzymes and its potential as an anti-cancer agent. Additionally, it has been studied for its possible use in the treatment of inflammatory and autoimmune diseases. However, further research is necessary to fully explore and understand its therapeutic applications.

Uses

Used in Pharmaceutical Industry:
1-(4-Bromophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine is used as an enzyme inhibitor for its potential to modulate biological processes by inhibiting specific enzymes, which can be crucial in the development of new drugs for various diseases.
Used in Cancer Research:
In cancer research, 1-(4-Bromophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine is used as a potential anti-cancer agent. Its study aims to understand its effects on cancer cells and to explore its potential to be developed into a therapeutic agent for cancer treatment.
Used in Treatment of Inflammatory and Autoimmune Diseases:
1-(4-Bromophenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine is also being studied for its potential use in the treatment of inflammatory and autoimmune diseases. Its role as a potential therapeutic agent is based on its capacity to influence the immune response and reduce inflammation, which are key factors in these types of conditions.

Upstream product

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

Downstream Products

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

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.