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:

1972-05-01

Pagination or Media Count:

42.0

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 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

Descriptors:

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

Subject Categories:

• Pharmacology

Distribution Statement:

APPROVED FOR PUBLIC RELEASE