Accession Number : AD0745131

Title :   Anthracene aminoalcohols as Antimalarials.

Descriptive Note : Final technical rept. 1 Jan-31 Dec 71,

Corporate Author : ESSO RESEARCH AND ENGINEERING CO LINDEN N J GOVERNMENT RESEARCH LAB

Personal Author(s) : Stogryn,Eugene L.

Report Date : MAY 1972

Pagination or Media Count : 42

Abstract : 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 Zn/NH4OH 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)

Descriptors :   (*ANTIMALARIALS, *ANTHRACENES), AMINES, ALCOHOLS, SYNTHESIS(CHEMISTRY), NUCLEAR MAGNETIC RESONANCE, REDUCTION(CHEMISTRY), HALOGENATED HYDROCARBONS, KETONES

Subject Categories : Pharmacology

Distribution Statement : APPROVED FOR PUBLIC RELEASE