136549-13-8

Basic information

• Product Name: 7-CHLORO-2,5-DIMETHYL-PYRAZOLO[1,5-A]PYRIMIDINE
• Synonyms: 7-CHLORO-2,5-DIMETHYL-PYRAZOLO[1,5-A]PYRIMIDINE;Pyrazolo[1,5-a]pyriMidine, 7-chloro-2,5-diMethyl-
• CAS NO: 136549-13-8
• Molecular Formula: C₈H₈ClN₃
• Molecular Weight: 182
• Mol File: 136549-13-8.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• Density: 1.37
• Refractive Index: 1.657
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.38±0.30(Predicted)
• CAS DataBase Reference: 7-CHLORO-2,5-DIMETHYL-PYRAZOLO[1,5-A]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-CHLORO-2,5-DIMETHYL-PYRAZOLO[1,5-A]PYRIMIDINE(136549-13-8)
• EPA Substance Registry System: 7-CHLORO-2,5-DIMETHYL-PYRAZOLO[1,5-A]PYRIMIDINE(136549-13-8)

Safety Data

• Hazardous Substances Data: 136549-13-8(Hazardous Substances Data)

Usage

Uses

7-Chloro-2,5-dimethylpyrazolo[1,5-a]pyrimidine is used as a reactant in the preparation of amino substituted pyrazolo[1,5-a]-1,5-pyrimidines and pyrazolo[1,5-a]-1,3,5-triazines as NPY receptor antagonists.

InChI:InChI=1/C8H8ClN3/c1-5-3-7(9)12-8(10-5)4-6(2)11-12/h3-4H,1-2H3

Upstream product

• 27166-46-7 2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-ol 
• 98488-10-9 2,7-dimethyl-1,4-dihydropyrazolo[1,5-a]pyrimidin-4-one 

Downstream Products

• 859160-63-7 C₁₅H₁₄FN₃ 
• 1031639-13-0 C₁₄H₁₄N₄ 
• 859160-51-3 C₁₅H₁₄FN₃O 

Relevant articles and documents

Phenoxide leaving group SNAr strategy for the facile preparation of 7-amino-3-aryl pyrazolo[1,5-a]pyrimidines from a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate

We have discovered a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate that allows for the direct sequential funtionalization of the 3-position and 7-position of a pyrazolo[1,5-a]pyrimidine scaffold. The intermediate and general method described herein offer an improvement over prior methods, particularly in cases where multiple unique 3-aryl substituents are to be incorporated in conjunction with multiple unique 7-amino substituents.

Comparative study between the anti-P. falciparum activity of triazolopyrimidine, pyrazolopyrimidine and quinoline derivatives and the identification of new PfDHODH inhibitors

In this work, we designed and synthesized 35 new triazolopyrimidine, pyrazolopyrimidine and quinoline derivatives as P. falciparum inhibitors (3D7 strain). Thirty compounds exhibited anti-P. falciparum activity, with IC50 values ranging from 0.030 to 9.1 μM. The [1,2,4]triazolo[1,5-a]pyrimidine derivatives were more potent than the pyrazolo[1,5-a]pyrimidine and quinoline analogues. Compounds 20, 21, 23 and 24 were the most potent inhibitors, with IC50 values in the range of 0.030–0.086 μM and were equipotent to chloroquine. In addition, the compounds were selective, showing no cytotoxic activity against the human hepatoma cell line HepG2. All [1,2,4]triazolo[1,5-a]pyrimidine derivatives inhibited PfDHODH activity in the low micromolar to low nanomolar range (IC50 values of 0.08–1.3 μM) and did not show significant inhibition against the HsDHODH homologue (0–30% at 50 μM). Molecular docking studies indicated the binding mode of [1,2,4]triazolo[1,5-a]pyrimidine derivatives to PfDHODH, and the highest interaction affinities for the PfDHODH enzyme were in agreement with the in vitro experimental evaluation. Thus, the most active compounds against P. falciparum parasites 20 (R = CF3, R1 = F; IC50 = 0.086 μM), 21 (R = CF3; R1 = CH3; IC50 = 0.032 μM), 23, (R = CF3, R1 = CF3; IC50 = 0.030 μM) and 24 (R = CF3, 2-naphthyl; IC50 = 0.050 μM) and the most active inhibitor against PfDHODH 19 (R = CF3, R1 = Cl; IC50 = 0.08 μM - PfDHODH) stood out as new lead compounds for antimalarial drug discovery. Their potent in vitro activity against P. falciparum and the selective inhibition of the PfDHODH enzyme strongly suggest that this is the mechanism of action underlying this series of new [1,2,4]triazolo[1,5-a]pyrimidine derivatives.

CONDENSED PYRIMIDINE OR PYRIDAZINE DERIVATIVES AS ANTIVIRAL AGENTS

A compound of formula (I) or a pharmaceutically acceptable salt thereof. The compound is a prodrug of a PI4KIIIβinhibitor and as such is useful as an antiviral agent. A pharmaceutical composition comprising the compound.

HETEROAROMATIC COMPOUNDS USEFUL IN THERAPY

A compound of formula (I) or a pharmaceutically acceptable salt thereof, useful in therapy, in particular in the treatment of a viral infection or a disease linked to impaired or abnormal autophagy.