57489-70-0

Usage

Uses

Used in Pharmaceutical Industry:
Pyrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione is used as a potential therapeutic agent for the treatment of various diseases, leveraging its anti-inflammatory and analgesic properties to alleviate pain and reduce inflammation.
Used in Cancer Treatment:
In the field of oncology, Pyrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione is utilized as an anticancer agent, targeting and inhibiting specific enzymes and pathways that are crucial for tumor growth and progression, thereby offering a novel approach to cancer therapy.
Used in Drug Development Research:
Pyrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione serves as a subject of ongoing research for the synthesis of new compounds and the exploration of its biological activities, with the aim of advancing its pharmaceutical potential and contributing to the development of innovative drugs for various medical conditions.

InChI:InChI=1/C6H5N3O2/c10-5-3-6(11)9-4(8-5)1-2-7-9/h1-2H,3H2,(H,8,10)

Upstream product

• 1225387-53-0 3⁽⁵⁾-aminopyrazole 
• 105-53-3 diethyl malonate 
• 1820-80-0 3-aminopyrazole 
• 140-88-5 ethyl acrylate 

Downstream Products

• 57489-77-7 5,7-dichloropyrazolo[1,5-a]pyrimidine 
• 245095-96-9 5-chloropyrazolo[1,5-a]pyrimidin-7-amine 
• 1251730-16-1 5-chloro-3-(6-phenylpyridin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine 
• 1260106-44-2 (Z)-ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(2-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate 
• 1260106-16-8 3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yloxy)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine 
• 1260105-84-7 3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yloxy)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine 
• 1260106-18-0 (Z)-tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(2-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate 
• 1260105-74-5 (R)-2-hydroxy-1-(4-(3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yl)piperidin-1-yl)propan-1-one 
• 1260105-83-6 (R)-1-(4-(6-chloro-3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yl)piperidin-1-yl)-2-hydroxypropan-1-one 
• 1260106-24-8 ethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-methylcyclohex-3-enecarboxylate 
• 1260106-25-9 ethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-methylcyclohex-3-enecarboxylate 
• 1260106-26-0 (Z)-ethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(2-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-methylcyclohex-3-enecarboxylate 
• 1260106-27-1 ethyl 1-methyl-4-(3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yl)cyclohex-3-enecarboxylate 
• 1260105-77-8 1-methyl-4-(3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yl)cyclohex-3-enecarboxylic acid 

Relevant academic research and scientific papers

Synthesis of two novel pyrazolo[1,5-a]pyrimidine compounds with antibacterial activity and biophysical insights into their interactions with plasma protein

Two novel water-soluble pyrazolo[1,5-a]pyrimidine derivatives, 5-chloro-7-(4-methyl-piperazin ?1-yl)-pyrazolo[1,5-a]pyrimidine (CMPS) and N′-(5-chloro-pyrazolo[1,5-a]pyrimidin-7-yl)-N,N-dimethyl -propane-1,3-diamine (NCPS), were synthesized and characterized with antibacterial activity. Then, the interactions of these compounds with bovine serum albumin (BSA) were studied by fluorescence, time-resolved fluorescence, circular dichroism (CD) spectroscopy and molecular docking. The results indicate that both CMPS and NCPS could effectively quench the intrinsic fluorescence of BSA via a static quenching process. The energy transfer from BSA to CMPS and NCPS may occur with high probability. Both CMPS and NCPS bind in the site I of BSA. The hydrophobic force and hydrogen bonds play major roles in the complex formation. Binding constants for both systems show that the affinity of CMPS binding to BSA is stronger than that of NCPS. The results of three-dimensional fluorescence and CD spectra reveal that the binding of CMPS and NCPS to BSA can induce conformational changes of BSA, and the influence of CMPS is slightly stronger than that of NCPS.

Discovery of dinaciclib (SCH 727965): A potent and selective inhibitor of cyclin-dependent kinases

Inhibition of cyclin-dependent kinases (CDKs) has emerged as an attractive strategy for the development of novel oncology therapeutics. Herein is described the utilization of an in vivo screening approach with integrated efficacy and tolerability paramete

TYK2 PSEUDOKINASE LIGANDS

Described herein are TYK2 pseudokinase ligands and methods of utilizing TYK2 pseudokinase ligands in the treatment of diseases, disorders or conditions. Also described herein are pharmaceutical compositions containing such compounds.

TYK2 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

Pyrazolo[1,5-a]pyrimidine derivative containing aryl hydrazone structure and application thereof

The invention relates to a pyrazolo[1,5-a]pyrimidine derivative containing an aryl hydrazone structure and application thereof, and belongs to the technical field of medicines. The pyrazolo[1,5-a]pyrimidine derivative containing the aryl hydrazone structure has a structure as shown in a general formula (I), and the derivative can be medically acidified to form salt. Pharmacological activity screening results show that the derivative has a significant inhibitory effect on human lung adenocarcinoma cells A549 and human colon cancer cells HT-29, and has good antitumor drug development and application prospects.

Pyrazolo[1,5-a]pyridine compounds and production method and application thereof

The invention discloses pyrazolo[1,5-a]pyridine derivatives and a production method and application thereof. The production method comprises the steps of using malonic diester and 3-aminopyrazole as raw materials, carrying out Michael addition reaction to obtain pyrazolo[1,5-a]pyridine-5,7-diol, using the pyrazolo[1,5-a]pyridine-5,7-diol and N,N-dimethylaniline as raw materials, carrying out Friedel-Crafts acylation reaction on the pyrazolo[1,5-a]pyridine-5,7-diol and the N,N-dimethylaniline to obtain 5,7-dichloro-pyrazolo[1,5-a]pyridine, and using the 5,7-dichloro-pyrazolo[1,5-a]pyridine and1-methyl piperazine or N,N-dimethyl-1,3-propanediamine as raw materials for synthesizing the CMPS and the NCPS. The pyrazolo[1,5-a]pyridine derivatives are applied for the field of antibiosis, thus the usage of antibiotics can be reduced, reasonable use of the antibiotics is promoted, and the problem of bacterial drug resistance brought by antibiotics abuse can be solved.

TYK2 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

Synthesis, Crystal Structure, and Antiproliferative Activity of Novel 7-Arylaminopyrazolo[1,5-a]pyrimidine Derivatives Containing the Hydrazone Moiety

A series of novel 7-arylaminopyrazolo[1,5-a]pyrimidine derivatives containing the hydrazone moiety has been synthesized by a five-step procedure including cyclization, chlorination, animation, hydrazinolysis, and condensation. Structures of the products have been characterized by IR, 1H NMR and MS spectra, and single-crystal X-ray diffraction. The bioassay results indicate most of the compounds as potentially antiproliferation agents against A549 and HT-29 cell lines. Among those, compounds 6e and 6f exhibit remarkable inhibitory activity against HT-29 cell lines, that are comparable with that of the positive control sorafenib. Preliminary structure-activity relationship is considered.

PYRAZOLOPYRIMIDINE PDE10 INHIBITORS

The present invention is directed to pyrazolopyrimidine compounds which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 10 (PDE10). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

Discovery of pyrazolopyrimidine phosphodiesterase 10A inhibitors for the treatment of schizophrenia

Herein, we present the identification of a novel class of pyrazolopyrimidine phosphodiesterase 10A (PDE10A) inhibitors. Beginning with a lead molecule (1) identified through a fragment-based drug discovery (FBDD) effort, lead optimization was enabled by rational design, X-ray crystallography, metabolic and off-target profiling, and fragment scaffold-hopping. We highlight the discovery of PyP-1, a potent, highly selective, and orally bioavailable pyrazolopyrimidine inhibitor of PDE10A. PyP-1 exhibits sub-nanomolar potency (PDE10A Ki = 0.23 nM), excellent pharmacokinetic (PK) and physicochemical properties, and a clean off-target profile. It displays dose-dependent efficacy in numerous pharmacodynamic (PD) assays that measure potential for anti-psychotic activity and cognitive improvement. PyP-1 also has a clean preclinical profile with respect to cataleptic potential in rats, prolactin secretion, and weight gain, common adverse events associated with currently marketed therapeutics. Further, PyP-1 displays in vivo preclinical target engagement as measured by PET enzyme occupancy in concert with [11C]MK-8193, a novel PDE10A PET tracer.