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The preparation and characterization of diastereomeric (+)-quinicinol

Author

Ronald Timpe, University of the Pacific

Date of Award

1976

Document Type

Thesis

Degree Name

Master of Science (M.S.)

Department

Graduate School

First Advisor

Charles A. Matuszak

First Committee Member

Herschel Frye

Second Committee Member

Donald K. Wedegaertner

Abstract

Female Anopheles mosquitoes are the only known vectors of human malaria (1) so that eradication of the disease depends on either eliminating the Anopheles mosquito or controlling the Plasmodium organism. In the U.S., Fiji Islands, Hawaii, and Guam, the absence of malaria is due to the absence or elimination of the Anopheles (1). Where the mosquito is less easily eliminated, the Plasmodium parasite must be controlled, and so the quest for effective antiplasmodial drugs is a continuing effort. More than 20,000 drugs (1), 14,000 of which were investigated between 1941-1945 (2), have been studied in regard to their aniplasmodial effect. Although many have found to have some activity, quinine (I) (see Fig. 1) (obtained from the bark of the Cinchona tree) is still listed among the most effective (1, 3, 4). Consequently, there has been much study done on isomers and derivatives of quinine, where the vinyl group on C-3, various substituents or, and the stereochemistry of, C-9, and C-8 to N-1 bond are of major interest, as well as on compounds having structural similarities to quinine (3). The recent report of antimalarial activity of quinicine raises the question of whether or not the activity might be enhanced if the carbonyl group were reduced to the alcohol but the vinyl group left intact, resulting in a pair of diastereomeric quinicinls (XI) (see Fig. 1.) The diastereomeric quinicinls differ from quinicine at C-9 and from dihydroquinicinols at C-3. The presence of the hydroxyl group and the vinyl group, both of which have been mentioned as affecting the activity of Cinchona alkaloids, is expected to make the compounds more active than quinicine. This research was undertaken in an attempt to prepare, isolate, and characterize the diastereomeric quinicinols.

Pages

50

Recommended Citation

Timpe, Ronald. (1976). The preparation and characterization of diastereomeric (+)-quinicinol. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/437