Anthracene aminoalcohols as Antimalarials.
Final technical rept. 1 Jan-31 Dec 71,
ESSO RESEARCH AND ENGINEERING CO LINDEN N J GOVERNMENT RESEARCH LAB
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The synthesis and antimalarial activity of anthracene aminoalcohols are described. The target anthraceneaminoalcohols were prepared to assess the relative merits of having the aminoalcohol sidechain in the 1-, 20, or 9-positions of the anthracene ring. Also evaluated were variations in which the ring was substituted by one or two chlorine atoms. Requisite 1- and 2-anthroic acids were obtained via oxidation of benzanthrones and methylanthraquinones followed by ZnNH4OH reduction. Conversion of the carboxylic acid group to the aminoalcohol function was realized via a modified Lutz procedure. This technique failed with chlorine substituted 9-anthroic acids. Functionalization of a dichloro-9-anthraldehyde via the corresponding oxirane yielded dichloro-9-anthracene-aminoalcohols. All the target anthraceneaminoalcohols exhibited activity in the rodent antimalarial screen. 4,5-Dichloro-9-2-dibutylamine-1-hydroxyethyl anthracene was very active. Author