Synthesis of heterocyclic bases derived from m-phenanthroline of possible antimalarial activity

Abstract

#I. A survey of the literature dealing with antimalarial compounds is given, with special reference to the relationship between chemotherapeutic activity and chemical constitution. #II. The relation between various isomeric derivatives of m-phenanthroline is discussed and the constitution of certain new compounds and of orientation has been established. #III. The condensation of m -amino acetanilide with ethyl aceto acetate has been carried out and the product cyclised by the method. of Conrad and. Limpach. It has been shown that the compound so obtained is 5-acetylamino-4-hydroxy-2-methyl quinoline and not the isomeric 7-acetylamino derivative. #IV. The following chloro derivatives of m-phenanthroline have been prepared: 2-methyl-4-chloro-5:6, 21:3'-pyrido quinoline; 2-methyl-4-chloro7:8,2':3'-pyrido quinoline; 2-chloro-4-methyl-7:8,2'3'-pyrido quinoline; 2-chloro-5:6,2': 3'-pyrido quinoline and 2-chloro-7:8,2':3'- pyrido quinoline. It is shown that the chloro n-phenanthroline described in D.R.P. 654,444 (C. 1938, I, 2023) and assumed to be 2-chloro-5:6,2':3'-pyrido quinoline does in fact have this structure, and is not the isomeric 2-chloro-7:8,2':3'-pyrido quinoline. #V. The first four of the above chloro compounds were condensed with the appropriate bases to yield respectively: 4-(ß-diethylamino ethylamino) -2- -5:6,2':3'-pyrido quinoline and 4-(α-methyl- δ-diethylamino butyl amino)-2-methyl-5:6,2':3'-pyrido quinoline; 4-(ß-diethylamino ethyl amino)-2-methyl-7:8,2':3'-pyrido quinoline and 4-(α-methyl-δ-diethylamino-butyl amino)-7:8,2':3'- pyrido quinoline; 2-(P-diethylamino ethyl amino)-4-methyl- 7:8,2' :3'- pyrido quinoline and 2-(α-methyl-δ-diethylamino-butyl amino)-7:8,21:31-pyrido quinoline; 2-(ß-diethylamino ethyl amino)-5:6,2': 3'-pyrido quinoline and 2-(α-methyl-δ-diethylamino-butyl amino)- 5:6,2:3'- pyrido quinoline

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