245449-98-3

Usage

Chemical class

Pyrazolo[3,4-d]pyrimidine derivative It belongs to a group of compounds derived from the pyrazolo[3,4-d]pyrimidine core structure.

Functional groups

Phenyl group and piperazine moiety The compound contains a phenyl group (a ring of six carbon atoms with a single bond to a hydrogen atom) and a piperazine moiety (a five-membered ring with four nitrogen atoms and one carbon atom).

Potential pharmacological properties

1-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine has been investigated for its activities in the central nervous system, suggesting possible therapeutic applications.

Psychoactive substance potential

The compound may have psychoactive effects, making it a potential candidate for further research in the development of new psychoactive substances.

Interaction with neural receptors and neurotransmitters

The structure of the compound suggests that it may interact with specific neural receptors and neurotransmitters, which could be relevant for its pharmacological effects.

Upstream product

• 110-85-0 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 

Downstream Products

• 579494-70-5 4-(4-(methylsulfonyl)piperazin-1-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 393846-02-1 4-(4-(4-methoxyphenyl)piperazin-1-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 

Relevant academic research and scientific papers

Identification of novel GLUT inhibitors

The compound class of 1H-pyrazolo[3,4-d]pyrimidines was identified using HTS as very potent inhibitors of facilitated glucose transporter 1 (GLUT1). Extensive structure–activity relationship studies (SAR) of each ring system of the molecular framework was established revealing essential structural motives (i.e., ortho-methoxy substituted benzene, piperazine and pyrimidine). The selectivity against GLUT2 was excellent and initial in vitro and in vivo pharmacokinetic (PK) studies are encouraging.

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.

GLUCOSE TRANSPORT INHIBITORS

The present invention relates to chemical compounds of general formula (I): in which RA, RB, RC, RD, m, and n are as given in the description and in the claims, and which effectively and selectively inhibit glucose transporter 1 (GLUT1), to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds.

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.