305337-65-9

Basic information

• Product Name: 4-[4-(4-chlorophenyl)-1-piperazinyl]-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine
• Synonyms: 4-[4-(4-chlorophenyl)-1-piperazinyl]-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine
• CAS NO: 305337-65-9
• Molecular Formula: C₂₁H₁₉ClN₆
• Molecular Weight: 390.86876
• Mol File: 305337-65-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-[4-(4-chlorophenyl)-1-piperazinyl]-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[4-(4-chlorophenyl)-1-piperazinyl]-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine(305337-65-9)
• EPA Substance Registry System: 4-[4-(4-chlorophenyl)-1-piperazinyl]-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine(305337-65-9)

Safety Data

• Hazardous Substances Data: 305337-65-9(Hazardous Substances Data)

Upstream product

• 38212-33-8 4-(4-chlorophenyl) piperazine 
• 5334-48-5 4-chloro-1-(phenyl)-1H-pyrazolo[3,4-d]pyrimidine 
• 21314-17-0 1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 100-63-0 phenylhydrazine 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 16078-71-0 ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate 

Relevant articles and documents

4-Substituted-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine derivatives: Design, synthesis, antitumor and EGFR tyrosine kinase inhibitory activity

Four series of some 4-substituted-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine derivatives 5a-f, 6a-f, 8a-f, and 9a-f were designed to be screened for their antitumor activity. All compounds were evaluated against breast (MCF-7) and lung (A-549) cell lines. Six compounds 5a, 5b, 6b, 6e, 9e, and 9f displaying activity against both cell lines were further estimated for their EGFR-TK inhibitory activity where they revealed 41-91% inhibition and compound 6b elicited the highest activity (91%). A docking study of these compounds into the ATP-binding site of EGFR-TK demonstrated their binding mode where H-bonding interaction with Met793 through N1 of pyrimidine or N2 of pyrazole was observed. Four series of compounds comprising the pyrazolo[3,4-d]pyrimidine core substituted at position 4 with various heterocyclic substitutions were synthesized. Antitumor activity and EGFR-TK inhibition were evaluated.

Novel pyrazolopyrimidine derivatives targeting COXs and iNOS enzymes; Design, synthesis and biological evaluation as potential anti-inflammatory agents

A novel set of 4-substituted-1-phenyl-pyrazolo[3,4-d]pyrimidine and 5-substituted-1-phenyl-pyrazolo[3,4-d]pyrimidin-4-one derivatives were synthesized and evaluated as potential anti-inflammatory agents. The newly prepared compounds were assessed through the examination of their in vitro inhibition of four targets; cyclooxygenases subtypes (COX-1 and COX-2), inducible nitric oxide synthase (iNOS) and nuclear factor kappa B (NF-κB). Compounds 8a, 10c and 13c were the most potent and selective ligands against COX-2 with inhibition percentages of 79.6%, 78.7% and 78.9% at a concentration of 2 μM respectively, while compound 13c significantly inhibited both COX subtypes. On the other hand, fourteen compounds showed high iNOS inhibitory activities with IC50 values in the range of 0.22-8.5 μM where the urea derivative 11 was the most active compound with IC50 value of 0.22 μM. Most of the tested compounds were found to be devoid of inhibitory activity against NF-kB. Moreover, almost all compounds were not cytotoxic, (up to 25 μg/ml), against a panel of normal and cancer cell lines. The in silico docking results were in agreement with the in vitro inhibitory activities against COXs and iNOS enzymes. The results of in vivo anti-inflammatory and antinociceptive studies were consistent with that of in vitro studies which confirmed that compounds 8a, 10c and 13c have significant anti-inflammatory and analgesic activities comparable to that of the control, ketorolac. Taken together, dual inhibition of COXs and iNOS with novel pyrazolopyrimidine derivatives is a valid strategy for the development of anti-inflammatory/ analgesic agents with the probability of fewer side effects.