245449-97-2

Usage

Core Structure

Pyrazolo[3,4-d]pyrimidine
A fused bicyclic ring system consisting of a pyrazole and a pyrimidine ring.

Side Chain

Piperazinyl
A heterocyclic ring system containing two nitrogen atoms, which provides versatility as a chemical intermediate.

Classification

Heterocyclic compound
A compound containing one or more heteroatoms (e.g., nitrogen, oxygen, or sulfur) within a ring structure.

Potential Applications

Pharmacological
The compound may have potential applications in the field of medicine due to its structural features.

Versatility

Chemical intermediate
The presence of the piperazinyl group makes it a useful building block for the synthesis of various biologically active compounds.

Research Interest

Medicinal chemistry and drug discovery
The unique structure and potential applications of 1-Methyl-4-piperazin-1-yl-1H-pyrazolo[3,4-d]pyrimidine make it an interesting target for further research and development in these fields.

Upstream product

• 59377-19-4 p-phenoxyphenylisocyanate 
• 245449-27-8 4-(2-Amino-6-purinyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide 
• 110-85-0 piperazine 
• 5334-56-5 4-hydroxy-1-methyl-1H-pyrazolo[3,4-d]pyrimidine 
• 23000-43-3 4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine 

Relevant academic research and scientific papers

Potent and Selective Inhibitors of Platelet-Derived Growth Factor Receptor Phosphorylation. 3. Replacement of Quinazoline Moiety and Improvement of Metabolic Polymorphism of 4-[4-(N-Substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline Derivatives

We have previously reported that a series of 4-[4-(N-substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives were potent and selective inhibitors of platelet-derived growth factor receptor (PDGFR) phosphorylation and demonstrated several biological effects such as suppression of neointima formation following balloon injury in rat carotid artery by oral administration. Here, we investigated structure-activity relationships of the 6,7-dimethoxyquinazolinyl moiety. In regard to 6,7-dimethoxy groups, ethoxy analogues showed potent activity (IC50 of 16b is 0.04 μM; IC50 of 17a is 0.01 μM) and further extension of the alkyl group reduced activity. Interestingly, methoxyethoxy (IC50 of 16j is 0.02μM; IC50 of 17h is 0.01 μM) and ethoxyethoxy (IC50 of 17j is 0.02 μM) analogues showed the most potent activity, suggesting that the inserted oxygen atom significantly interacts with β-PDGFR. Among tricyclic quinazoline derivatives, the 2-oxoimidazo[4,5-e]quinazoline derivative 21a showed potent activity (IC 50 = 0.10 μM). Regarding replacements of quinazoline by other heterocyclic rings, pyrazolo[3,4-d]pyrimidine (39a, IC50 = 0.17 μM) and quinoline (IC50 of 40a is 0.18 μM; IC50 of 40b is 0.09 μM) derivatives showed potent activity. Isoquinoline and some pyridopyrimidine derivatives were completely inactive; therefore, 1-aza has an important role. Also 7-aza and 8-aza substitution on the parent quinazoline ring has a detrimental effect on the interaction with β-PDGFR. We also demonstrated that the substituents on the quinazoline ring possess major consequences for metabolic polymorphism. Although there existed extensive metabolizers and poor metabolizers in Sprague-Dawley rats administrated 6,7-dimethoxyquinazoline derivatives (1b and 1c), 6-(2-methoxy)ethoxy-7-methoxyquinazoline analogue 16k showed no metabolic polymorphism.

Nitrogenous heterocyclic compounds

The present invention relates to nitrogen-containing heterocyclic compounds represented by formula (I): STR1wherein W represents 1,4-piperazinediyl, etc.; U represents NR 1 R 2 (wherein R 1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, etc.; and R 2 represents a hydrogen atom, etc. ), OR 4, or SR 5 ; V represents an oxygen atom, a sulfur atom, N--R 6, or CR 7 R 8, at least one of X, Y and Z represents a nitrogen atom, and the others are the same or different, and each represents a nitrogen atom or C--R A ; and D 1, D 2, D 3 and D 4 each independently represent C--R B, a nitrogen atom, an oxygen atom, a sulfur atom, etc., optional adjoining two among D 1 to D 4 are combined to represent a nitrogen atom, N--R 2A, an oxygen atom, a sulfur atom, etc., or optional adjoining two selected from D 1 to D 4 represent C--R B"" (wherein two R B"" s are combined to represent substituted or unsubstituted alicyclic alkene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazole, etc.; or pharmaceutically acceptable salts thereof.