16401-66-4Relevant articles and documents
Hydrolysis of 4-amino-3-quinolinesulfonamides
Skrzypek, Leszek
, p. 1249 - 1254 (1998)
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.
Introduction of alkylamino and dialkylamino groups into the quinoline
LUTHY,BERGSTROM,MOSHER
, p. 1109 - 1109 (1949)
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Structure-activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods
Nsumiwa, Samkele,Kuter, David,Wittlin, Sergio,Chibale, Kelly,Egan, Timothy J.
supporting information, p. 3738 - 3748 (2013/07/19)
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.
PERACID OXIDATION OF (METHYLAMINO)QUINOLINES
Pentimalli, Luciano,Milani, Giovanni
, p. 803 - 806 (2007/10/02)
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.