214633-89-3

Basic information

• Product Name: [1,2,4]Triazolo[1,5-a]pyrimidin-7-amine, 5-chloro-N-(2,2,2-trifluoroethyl)-6-(2,4,6-trifluorophenyl)-
• CAS NO: 214633-89-3
• Molecular Formula: C13H6ClF6N5
• Molecular Weight: 381.668
• Mol File: 214633-89-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: [1,2,4]Triazolo[1,5-a]pyrimidin-7-amine, 5-chloro-N-(2,2,2-trifluoroethyl)-6-(2,4,6-trifluorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: [1,2,4]Triazolo[1,5-a]pyrimidin-7-amine, 5-chloro-N-(2,2,2-trifluoroethyl)-6-(2,4,6-trifluorophenyl)-(214633-89-3)
• EPA Substance Registry System: [1,2,4]Triazolo[1,5-a]pyrimidin-7-amine, 5-chloro-N-(2,2,2-trifluoroethyl)-6-(2,4,6-trifluorophenyl)-(214633-89-3)

Safety Data

• Hazardous Substances Data: 214633-89-3(Hazardous Substances Data)

Upstream product

• 214707-02-5 5,7-dichloro-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine 
• 753-90-2 trifluoroethylamine 
• 262609-07-4 diethyl (2,4,6-trifluoro-phenyl)-malonate 

Downstream Products

• 849600-50-6 N-[5-chloro-3-methyl-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7(3H)-ylidene]-2,2,2-trifluoroethanamine 
• 1036758-28-7 {5-Chloro-6-[2,6-difluoro-4-(3-methoxypropoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl}-(2,2,2-trifluoroethyl)amine 

Relevant articles and documents

HETEROCYCLIC COMPOUNDS AND THEIR USE FOR THE TREATMENT OF NEURODEGENERATIVE TAUOPATHIES

The present invention is directed to triazolopyrimidine, phenylpyrimidine, pyridopyridazine, and pyridotriazine compounds and their use in the treatment of neurodegenerative disorders.

Synthesis and SAR of [1,2,4]triazolo[1,5-a]pyrimidines, a class of anticancer agents with a unique mechanism of tubulin inhibition

The synthesis and SAR of a series of triazolopyrimidines as anticancer agents are described. Treatment of 5-chloro-6-(trifluorophenyl)-N-fluoroalkyl[1, 2,4]triazolo[1,5-a]pyrimidin-7-amine with an alcohol, a thiol, or an alkylamine provided the corresponding final compounds. A clear SAR requirement has been established for optimal activity. A (1S)-2,2,2-trifluoro-1-methylethylamino group or an achiral 2,2,2-trifluoroethylamino group is required at the 5-position to achieve high potency. On the phenyl ring, both fluoro atoms, at the positions ortho to the triazolopyrimidine core, are needed for optimal activity. At the position para to the triazolopyrimidine core, on the phenyl ring, the best activity is achieved with an oxygen linkage followed by a three-methylene unit, and an alkylamino or a hydroxy group. The mechanism of action for this series of triazolopyrimidines was shown to be unique in that they promoted tubulin polymerization in vitro, but did not bind competitively with paclitaxel. Instead, they inhibit the binding of vincas to tubulin. Selected compounds were studied further, and it was shown that these compounds were able to overcome resistance attributed to several multidrug resistance transporter proteins. Lead compounds were shown to inhibit tumor growth in several nude mouse xenograft models, with high potency and efficacy, when dosed either orally or intravenously.

Fungicidal trifluorophenyl-triazolopyrimidines

The novel compounds of formula I: (R1, R2 and Hal are defined in the specification) show selective fungicidal activity. The new compounds are processed with carriers and adjuvants to fungicidal compositions.