57489-77-7

Basic information

• Product Name: 5,7-DICHLOROPYRAZOLO[1,5-A]PYRIMIDINE
• Synonyms: 5,7-DICHLOROPYRAZOLO[1,5-A]PYRIMIDINE;7-dichloropyrazolo[1;Pyrazolo[1,5-a]pyrimidine, 5,7-dichloro-
• CAS NO: 57489-77-7
• Molecular Formula: C₆H₃Cl₂N₃
• Molecular Weight: 188.01
• Product Categories: CHIRAL CHEMICALS;Heterocycle-Pyrimidine series
• Mol File: 57489-77-7.mol

Chemical Properties

• Melting Point: 68-71 °C(Solv: ethanol (64-17-5))
• Appearance: /
• Density: 1.696 g/cm³
• Refractive Index: 1.733
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -1.68±0.30(Predicted)
• CAS DataBase Reference: 5,7-DICHLOROPYRAZOLO[1,5-A]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-DICHLOROPYRAZOLO[1,5-A]PYRIMIDINE(57489-77-7)
• EPA Substance Registry System: 5,7-DICHLOROPYRAZOLO[1,5-A]PYRIMIDINE(57489-77-7)

Safety Data

• Hazardous Substances Data: 57489-77-7(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
5,7-Dichloropyrazolo[1,5-a]pyrimidine is used as a kinase inhibitor for its potential biological activities. It plays a crucial role in the development of pharmaceuticals targeting specific kinases involved in various diseases, including cancer and inflammatory conditions.
Used in Organic Synthesis:
As a versatile building block, 5,7-Dichloropyrazolo[1,5-a]pyrimidine is used in the synthesis of a wide range of organic compounds. Its unique structure allows for the creation of novel molecules with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Research:
5,7-Dichloropyrazolo[1,5-a]pyrimidine is employed as a key intermediate in the development of new drugs. Its ability to be modified and incorporated into complex molecular structures makes it an attractive candidate for the design of innovative therapeutic agents.
Used in Drug Discovery:
In the field of drug discovery, 5,7-Dichloropyrazolo[1,5-a]pyrimidine serves as a starting point for the exploration of new chemical entities. Its unique properties and reactivity enable researchers to probe its potential as a precursor to novel bioactive molecules.
Used in Chemical Research:
5,7-Dichloropyrazolo[1,5-a]pyrimidine is utilized in chemical research to study its reactivity, stability, and potential applications in various chemical reactions. Understanding its properties and behavior can lead to the development of new synthetic methods and the discovery of new compounds with unique properties.

InChI:InChI=1/C6H3Cl2N3/c7-4-3-5(8)11-6(10-4)1-2-9-11/h1-3H

Upstream product

• 672323-32-9 pyrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione 
• 57489-70-0 5,7-dihydroxypyrazolo[1,5-a]pyrimidine 
• 1820-80-0 3-aminopyrazole 
• 105-53-3 diethyl malonate 
• 121-69-7 N,N-dimethyl-aniline 
• 124-40-3 dimethyl amine 

Downstream Products

• 99898-84-7 5-chloropyrazolo<1,5-a>pyrimidin-7-one 
• 220456-74-6 5-chloro-7-<<2'-cyanobiphenyl-4-yl>methyl>pyrazolo<1,5-a>pyrimidine 
• 167371-95-1 4'-<(5-chloropyrazolo<1,5-a>pyrimidin-7-yl)aminomethyl>biphenyl-2-carbonitrile 
• 167371-96-2 4'-<(pyrazolo<1,5-a>pyrimidin-7-yl)aminomethyl>biphenyl-2-carbonitrile 
• 244127-62-6 4'-<(5-methylthiopyrazolo<1,5-a>pyrimidin-7-yl)methyl>biphenyl-2-carbonitrile 
• 244127-61-5 4'-<(5-methoxypyrazolo<1,5-a>pyrimidin-7-yl)methyl>biphenyl-2-carbonitrile 
• 244127-63-7 4'-<(5-dimethylaminopyrazolo<1,5-a>pyrimidin-7-yl)methyl>biphenyl-2-carbonitrile 
• 244127-56-8 4'-<(5-methylthiopyrazolo<1,5-a>pyrimidin-7-yl)aminomethyl>biphenyl-2-carbonitrile 
• 244127-54-6 4'-<(5-methoxypyrazolo<1,5-a>pyrimidin-7-yl)aminomethyl>biphenyl-2-carbonitrile 
• 244127-57-9 4'-<(5-dimethylaminopyrazolo<1,5-a>pyrimidin-7-yl)aminomethyl>biphenyl-2-carbonitrile 
• 244127-55-7 4'-<(5-ethoxypyrazolo<1,5-a>pyrimidin-7-yl)aminomethyl>biphenyl-2-carbonitrile 
• 244127-53-5 N-(5-chloropyrazolo<1,5-a>pyrimidin-7-yl)-N-(2'-cyanobiphenyl-4-ylmethyl)carbamic acid tert-butyl ester 

Relevant articles and documents

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.

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.

Structural optimization of pyrazolo[1,5-a]pyrimidine derivatives as potent and highly selective DPP-4 inhibitors

Our previous discovery of pyrazolo [1,5-a]pyrimidin-7(4H)-one scaffold-based DPP-4 inhibitors yielded two potent compounds b2 (IC50 = 79 nM) and d1 (IC50 = 49 nM) but characterized by cytotoxicity. Herein, with scaffold hopping and fragment-based drug design strategies, highly potent and selective pyrazolo [1,5-a]pyrimidine DPP-4 inhibitors were found featured by reduced or diminished cytotoxicity. Specifically, c24 (IC50 = 2 nM) exhibits a 25 to 40-fold increase of inhibitory activity respect to those of b2 and d1, respectively, 2-fold from Alogliptin (IC50 = 4 nM), and remarkable selectivity over DPP-8 and DPP-9 (>2000 fold). Further docking studies confirmed that the pyrazolo [1,5-a]pyrimidine core interacts with the S1 pocket whereas its substituted aromatic ring interacts with the sub-S1 pocket. The interactive mode in this case resembles that of Alogliptin and Trelagliptin. Further in vivo IPGTT assays in diabetic mice demonstrated that c24 effectively reduces glucose excursion by 48% at the dose of 10 mg/kg, suggesting that c24 is worthy of further development as a potent anti-diabetes agent.

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.

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.

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.

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.

LRRK2 INHIBITORS AND METHODS OF MAKING AND USING THE SAME

Compounds having the formula (I), (II), (III) are provided. Compounds of the present disclosure are useful for the treatment of neurodegenerative diseases, such as Parkinson's Disease.