105640-81-1

Basic information

• Product Name: 1-(4-bromo-phenyl)-4-chloro-6-methyl-1H-pyrazolo[3,4-d]pyrimidine
• Synonyms: 1-(4-bromo-phenyl)-4-chloro-6-methyl-1H-pyrazolo[3,4-d]pyrimidine
• CAS NO: 105640-81-1
• Molecular Weight: 323.579
• Mol File: 105640-81-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(4-bromo-phenyl)-4-chloro-6-methyl-1H-pyrazolo[3,4-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-bromo-phenyl)-4-chloro-6-methyl-1H-pyrazolo[3,4-d]pyrimidine(105640-81-1)
• EPA Substance Registry System: 1-(4-bromo-phenyl)-4-chloro-6-methyl-1H-pyrazolo[3,4-d]pyrimidine(105640-81-1)

Safety Data

• Hazardous Substances Data: 105640-81-1(Hazardous Substances Data)

Upstream product

• 589-21-9 (4-bromophenyl)hydrazine 
• 5334-28-1 5-amino-1-(4-bromophenyl)-1H-pyrazole-4-carbonitrile 

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.