Phillips, Robert Edward (1953) Structural studies on febrifugine and isofebrifugine, alkaloids from Dichroa febrifuga. Studies on 4-quinazolones. Synthesis of some 8-aminoquinolines. Dissertation (Ph.D.), California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-05122003-110549
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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.
|Item Type:||Thesis (Dissertation (Ph.D.))|
|Degree Grantor:||California Institute of Technology|
|Division:||Chemistry and Chemical Engineering|
|Thesis Availability:||Public (worldwide access)|
|Defense Date:||1 January 1953|
|Default Usage Policy:||No commercial reproduction, distribution, display or performance rights in this work are provided.|
|Deposited By:||Imported from ETD-db|
|Deposited On:||13 May 2003|
|Last Modified:||26 Dec 2012 02:41|
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