74227-77-3

Basic information

• Product Name: 1-[7-(trifluoromethyl)quinolin-4-yl]triaza-1,2-dien-2-ium
• CAS NO: 74227-77-3
• Molecular Formula: C₁₀H₅F₃N₄
• Molecular Weight: 239.1761
• Mol File: 74227-77-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-[7-(trifluoromethyl)quinolin-4-yl]triaza-1,2-dien-2-ium(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[7-(trifluoromethyl)quinolin-4-yl]triaza-1,2-dien-2-ium(74227-77-3)
• EPA Substance Registry System: 1-[7-(trifluoromethyl)quinolin-4-yl]triaza-1,2-dien-2-ium(74227-77-3)

Safety Data

• Hazardous Substances Data: 74227-77-3(Hazardous Substances Data)

Usage

Molecular structure

1-[7-(trifluoromethyl)quinolin-4-yl]triaza-1,2-dien-2-ium is a chemical compound with a unique molecular structure, consisting of a quinoline ring with a trifluoromethyl group attached to the 7th position and a triaza-diene-ium moiety.

Quinoline ring

The compound contains a quinoline ring, which is a tricyclic, nitrogen-containing aromatic organic compound. Quinoline derivatives have been studied for their various biological activities, including anti-cancer, anti-malarial, and anti-inflammatory properties.

Trifluoromethyl group

The compound has a trifluoromethyl group (-CF3) attached to the 7th position of the quinoline ring. The presence of this group may impart unique chemical and pharmacological properties to the compound, making it of interest for further research and development.

Triaza-diene-ium moiety

The compound also contains a triaza-diene-ium moiety, which suggests that it may have potential applications in organic synthesis and catalysis due to its potential reactivity and coordination chemistry.

Potential applications

Due to its unique molecular structure and the presence of a quinoline ring and trifluoromethyl group, 1-[7-(trifluoromethyl)quinolin-4-yl]triaza-1,2-dien-2-ium may have potential applications in medicinal chemistry, organic synthesis, and catalysis.

Biological activities

Quinoline derivatives, like the compound in question, have been studied for their various biological activities, which include anti-cancer, anti-malarial, and anti-inflammatory properties.

Reactivity

The triaza-diene-ium moiety in the compound may contribute to its reactivity, making it a potential candidate for use in organic synthesis and catalysis.

Coordination chemistry

The triaza-diene-ium moiety may also be involved in coordination chemistry, which could be useful in the development of new catalysts or other applications in the field of chemistry.

Upstream product

• 346-55-4 4-chloro-7-trifluoromethyl quinoline 

Downstream Products

• 55300-29-3 antrafenine 
• 243666-11-7 7-trifluoromethyl-quinolin-4-ylamine 
• 22760-66-3 2-diazo-3-oxo-N-phenylbutanamide 

Relevant articles and documents

Structure-activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (log K) and inhibition of β-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, log K values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (π) of the group X. The log K values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% β-hematin inhibitory activity (log BHIA50) was found to correlate with log K and either meta (σm) or para (σp) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that log K values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of β-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible.

Synthesis of 4-azidoquinoline 1-oxides and related compounds.

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