16401-66-4

Upstream product

• 611-35-8 4-chloroquinoline 
• 74-89-5 methylamine 
• 123-39-7 N-Methylformamide 
• 157494-20-7 4-methylamino-N-methyl-3-quinolinesulfonamide 
• 157494-32-1 4-Methylamino-quinoline-3-sulfonic acid phenylamide 
• 157494-40-1 4-chloro-3-quinolinesulfonyl chloride 
• 205985-49-5 4-chloro-3-quinolinesulfonic acid 

Relevant academic research and scientific papers

Hydrolysis of 4-amino-3-quinolinesulfonamides

Acid hydrolysis of 4-amino-3-quinolinesulfonamides (3) gives 1,4-dihydro-4-oxo-3-quinolinesulfonamides (4), 4-aminoquinolines (5) or a mixture of these compounds. Part LIII in the series of Azinyl Sulfides.

Metal-free, redox-neutral, site-selective access to heteroarylamine via direct radical?radical cross-coupling powered by visible light photocatalysis

Transition-metal-catalyzed C?N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical?radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C?N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C?N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.

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-amino-3-quinolinesulfonic acids and 4-aminoquinolines

The hydrolysis of 4-chloro-3-quinolinesulfonyl chloride (1) gives 4-chloro-3-quinolinesulfonic acid (2) or 1,4-dihydro-4-oxo-3-quinolinesulfonic acid (3). Compound (2) reacts with primary and secondary aliphatic or primary aromatic amines to give 4-amino-

PERACID OXIDATION OF (METHYLAMINO)QUINOLINES

The peracid oxidation of 2-(dimethylamino)quinoline yields the amino oxide; from 2-methylamino- and 4-dimethylamino-quinoline the corresponding 1-oxides are obtained. 2-Dimetylamino- and 4-dimethylamino-quinoline 1-oxide can only be obtained via chloroquinoline 1-oxide.