885461-50-7

Basic information

• Product Name: 7-chloro-5-Methyl-2-(trifluoroMethyl)-[1,2,4]triazolo[1,5-a]pyriMidine
• Synonyms: [1,2,4]-Triazolo[1,5-a]-pyrimidine, 7-chloro-5-methyl-2-(trifluoromethyl)
• CAS NO: 885461-50-7
• Molecular Formula: C₇H₄ClF₃N₄
• Molecular Weight: 236.5816696
• Mol File: 885461-50-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-chloro-5-Methyl-2-(trifluoroMethyl)-[1,2,4]triazolo[1,5-a]pyriMidine(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloro-5-Methyl-2-(trifluoroMethyl)-[1,2,4]triazolo[1,5-a]pyriMidine(885461-50-7)
• EPA Substance Registry System: 7-chloro-5-Methyl-2-(trifluoroMethyl)-[1,2,4]triazolo[1,5-a]pyriMidine(885461-50-7)

Safety Data

• Hazardous Substances Data: 885461-50-7(Hazardous Substances Data)

Usage

General Description

7-chloro-5-Methyl-2-(trifluoroMethyl)-[1,2,4]triazolo[1,5-a]pyriMidine, also known as Rilmazafone, is a psychoactive drug with sedative and anxiolytic effects. It belongs to the class of triazolopyrimidine derivatives and is primarily used in the treatment of insomnia and anxiety disorders. Rilmazafone acts as a positive allosteric modulator of the GABA-A receptor, enhancing the inhibitory effects of the neurotransmitter GABA in the central nervous system. This results in sedative, anxiolytic, and muscle relaxant properties, making it effective in promoting sleep and reducing anxiety.

Upstream product

• 116529-17-0 2-(trifluoromethyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 

Downstream Products

• 900886-29-5 7-(4-chlorophenylamine)-5-methyl-2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidine 
• 946203-59-4 7-cyclohexylamine-5-methyl-2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidine 

Relevant articles and documents

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.

Novel Selective Inhibitor of Leishmania (Leishmania) amazonensis Arginase

Arginase is a glycosomal enzyme in Leishmania that is involved in polyamine and trypanothione biosynthesis. The central role of arginase in Leishmania (Leishmania) amazonensis was demonstrated by the generation of two mutants: one with an arginase lacking

ANTIMALARIAL AGENTS THAT ARE INHIBITORS OF DIHYDROOROTATE DEHYDROGENASE

Inhibitors of parasitic dihydroorotate dehydrogenase enzyme (DHOD) are candidate therapeutics for treating malaria. Illustrative of such therapeutic agents include the compound: and a triazolopyrimidine class of compounds that conform to Formula (IX): and their solvates, stereoisomers, tautomers and pharmaceutically acceptable salts.