4-Amino quinoline

Halofantrine was an important antimalarial drug. It is now infrequently used because of worldwide strain resistance phenomena. Tafenoquine is a new 8-amino-quinoline currently in clinical trials (Phase III) (Figure 8.26). ... 

Quinoline-8-arsinic add, obtained from 8-amino-quinoline in 83 per cent, yield, crystallises in white needles, M.pt. 230° C-, readily soluble in dilute alkali, sodium carbonate, and concentrated mineral acids, insoluble in dilute acids, alcohol, and cold water. When reduced... 

In the few cases that have been described, mild chronic hemolytic anemia is associated with deficiency of GSH-S/ The disorder is inherited in an autosomal recessive mode. Such people may also have more severe acute hemolytic crises when exposed to redox substances, such as 8-amino-quinolines or other oxidant drugs. 

OR Idowu, JO Peggins, TG Brewer, C Kelley. Metabolism of a candidate 8-amino-quinoline antimalarial agent, WR 238605, by rat liver microsomes. Drug Metab Dispos 23 1, 1995. 

They are active against the pre- or exoeiythrocytic form of the malarial parasite, but lack activity against the eiythrocytic forms. The 8-amino-quinolines possess gametocidal activity. They are used mainly for the radical cure of relapsing malaria like vivax malaria. 

The degree of toxicity in the 8-amino quinoline structural analogues appears to be directly associated with the degree of substitution at the terminal amino function. Using the said criterion pamaquine, having a tertiary amino moiety, happens to be more toxic than primaquine, having a... 

In another example of pyridine activation of C—H bonds, 8-amino-quinoline and picolinic acids promote Cu-catalyzed fluorination of y-sp C-H bonds (Scheme 43) (13JA9342).The arenes can be mono- or difluo-rinated. The reaction proceeds well for both electron-rich and electron-poor arenes it also works for heterocycles such as indoles and pyridines.The reaction does not affect key functional groups such as nitro, nitriles, and carboxylates. 

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