Abstract
Reaction of 4, 6-diaminoquinoline with 1 mole of acetic anhydride, acetyl chloride, or benzoyl chloride in pyridine chiefly affords a diacylated compound and recovery of the starting material, with a small amount of 6-benzoylamino derivative together with the recovery of the starting material and a dibenzoyl compound in the case of benzoylation. By heating 4, 6-diaminoquinoline with cyanuric acid chloride in acetone, in the presence of sodium carbonate, and heating the product with ethanolic ammonia or by reacting with 2-amino-4, 6-dichloro-s-trizine, bis (4-aminoquinolyl-6) melamine was obtained. Coupling of the diazotized 4, 6-diaminoquinoline with β-naphthol, 2, 6-diaminopyridine, 3-hydroxypyridine, or 8-hydroxypyridine afforded the corresponding 6-azo dyes. Antibacterial tests of these azo dyes and the melamine compound showed that none of them showed any better action than chloramphenicol and none possessed efficacy against Trypanosoma curzi. However, bis (4-aminoquinolyl-6) melamine and 4-amino-6-(2′, 6′-diaminopyridyl-3′) azoquinoline showed marked therapeutic effect against Trypanosoma gambiense.
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