Anthracene aminoalcohols as Antimalarials.
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)
Document Details
- Document Type
- Technical Report
- Publication Date
- May 01, 1972
- Accession Number
- AD0745131
Entities
People
- Eugene L. Stogryn