23121-14-4

Basic information

• Product Name: 1H-Pyrazolo[3,4-d]pyrimidine, 4-chloro-6-methyl-1-phenyl-
• CAS NO: 23121-14-4
• Molecular Formula: C12H9ClN4
• Molecular Weight: 244.683
• Mol File: 23121-14-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazolo[3,4-d]pyrimidine, 4-chloro-6-methyl-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazolo[3,4-d]pyrimidine, 4-chloro-6-methyl-1-phenyl-(23121-14-4)
• EPA Substance Registry System: 1H-Pyrazolo[3,4-d]pyrimidine, 4-chloro-6-methyl-1-phenyl-(23121-14-4)

Safety Data

• Hazardous Substances Data: 23121-14-4(Hazardous Substances Data)

Upstream product

• 100-63-0 phenylhydrazine 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 91974-63-9 6-methyl-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4(5H)-one 
• 50427-77-5 5-amino-1-phenyl-1H-pyrazole-4-carboxamide 
• 91974-63-9 4-hydroxy-6-methyl-1-phenyl-pyrazolo-[3,4-d] pyrimidine 
• 116943-84-1 6-methyl-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine 

Downstream Products

• 116943-84-1 6-methyl-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine 
• 1383659-07-1 N-propyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 100974-14-9 N-isopropyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1383659-08-2 N-butyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 107518-86-5 N-(furan-2-ylmethyl)-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1383659-09-3 6-methyl-4-(morpholin-4-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 5401-50-3 N-benzyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 5346-47-4 N-ethyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 459135-75-2 N-(2-methoxyphenyl)-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 132648-78-3 N,N-diethyl-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 116943-92-1 6-Methyl-5-(4-methyl-benzoyl)-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile 
• 116943-91-0 5-benzoyl-4,5-dihydro-6-methyl-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4-carbonitrile 
• 116944-08-2 4-(5-acetamido-1-phenyl-1H-pyrazol-4-yl)-5-amino-2-phenyloxazole 

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.

PYRAZOLO-PYRIMIDINE ANILINE COMPOUNDS

Compounds having the formula (I), where all substituents are as defined herein, and pharmaceutically acceptable salts, prodrugs, and solvates thereof, are useful as kinase inhibitors.