Structural Studies on Febrifugine and Isofebrifugine. Alkaloids from Dichroa Febrifuga. Studies on 4-Quinazolones. Synthesis of Some 8-Aminoquinolines

Author: Phillips, Robert Edward

Year: 1953

Degree: Dissertation (Ph.D.)

Advisors: Koepfli, Joseph Blake; Buchman, Edwin Raphael

Committee Member: Unknown, Unknown

Option: Chemistry; Biology

DOI: 10.7907/QQS1-H154

Abstract

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Structural studies on two isomeric, antimalarial alkaloids, febrifugine and isofebrifugine, isolated from Dichroa febrifuga, have been continued. The basic structure of both alkaloids is proposed to be 3-[[Beta]-keto ?[gamma]-(3-hydroxy-2-piperidyl)propyl]-4-quinazalone, and the relationship of febrifugine and isofebrifugine to this structure is discussed.

Febrifugine is shown to be polymorphic, and evidence is presented that the alkaloid [gamma]-dichroine, from Dichroa febrifuga, is not chemically distinct, but a mixture of two of the crystalline modifications of febrifugine.

The synthesis of some 3-substituted-4-quinazolones is described. These are shown to be unreactive to benzenesulfonyl chloride, while the parent substance, 4-quinazolone, forms 3-benzenesulfonyl-4-quinazolone. The structure of a hydrolysis product of the letter compound is proposed to be N-(N?-formyl-[?]-aminobenzoyl) benzenesulfonamide, and the synthesis of this and of some related compounds is described.

The synthesis of some 8-aminoquinolines related to isoplasmocid was carried out as part of a cooperative project to study to study their action on experimental poliomyelitis in monkeys. These compounds were tested elsewhere and found to be without specific activity.

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