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Synthesis of chemotherapeutic agents derived from 2:3-benz-γ-carboline and 2:3:4':3'-quinoquinoline

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StoreyNE_1949redux.pdf (25.93Mb)
Date
1949
Author
Storey, Nora E.
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Abstract
 
 
1. From diethylethoxymethylene malonate and the appropriate aniline, 4-chloroquinoline, 6-methoxy-4-chloroquinoline and L.:6-dichloroquinoline have been prepared. 2. These chloro compounds have been used in the synthesis of 2:3-benz-γ-carboline, 15-methoxy-2:3-benz-γ-carboline and 15- chloro -2:3- benz -ycarboline. The unambiguous synthesis of the former base has cleared up certain discrepancies which existed in the literature. 3. The 2:3-benz-γ-carbolines have been treated with diethylaminoethyl chloride to obtain basic side chain derivatives. In this way, the following have been prepared: 1-diethylaminoethyl- 2:3-benz-γ- carboline . 4-diethylaminoethyl-2:3-benz-γ-isocarboline. 5-methoxy-4-diethylaminoethyl-2:3-benz-γ-isocarboline. 15-chloro-l-diethylaminoethyl-2:3-benz-γ-carboline. 15-chloro-4-diethylaminoethyl-2:3-benz-γ-isocarboline. In addition, 4-methyl-2:3-benz-γ-isocarboline and 15-chloro-4-methyl-2:3-benz-γ-isocarboline were also prepared. 4. The constitution of 1-diethylaminoethyl-2:3:4'-3'0benz-γ-carboline (and by analogy, of the corresponding 15-methoxy- and 15-chloro-compounds) has been established from a study of its methiodides. 5. The synthesis of 2:3:4':3'-quinoquinolo-4-one, 6'-methoxy-2:3:4':3'-quinoquinolo-4-one, 6'-chloro-2:3:4':3'-quinoquinolo-4-one, and of 4-chloro-2:3:4':3'-quinoquinoline, 6'-methoxy-4-chloro-2:3:4':3'-quinoquinoline and 4:6'-dichloro-2:3:4':3'-quinoquinoline from the corresponding 4-anilinoquinoline-3-carboxylic acids, has been described. These compounds are isomeric with the 5-chloropyridoacridines, which they resemble markedly in properties. 6. From the above chloroquinoquinolines, bases have been obtained by condensing them with amines such as ammonia, diethylaminoethylamine and 2-amino-5-diethylaminopentane. The constitution of the products obtained is still uncertain.
 
URI
http://hdl.handle.net/1842/34116
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  • Biological Sciences thesis and dissertation collection

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