QUINOLINEQUINONES .5. 6-CHLORO-5,8-QUINOLINEQUINONE AND 7-CHLORO-5,8-QUINOLINEQUINONE
QUINOLINEQUINONES .5. 6-CHLORO-5,8-QUINOLINEQUINONE AND 7-CHLORO-5,8-QUINOLINEQUINONE
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DOI：
10.1021/ja01490a035
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发表时间：
1960-01-01
影响因子：
15
通讯作者：
DRAKE, NL
中科院分区：
文献类型：
--
作者：
PRATT, YT;DRAKE, NL
合成了6-氯和7-氯-5，8-喹啉醌（II和III），并通过与重氮盐反应在醌环的未取代位置引入芳基，通过过氧化物烷基化引入烷基。7-芳基-6-氯-和6-芳基-7-氯-5，8-喹啉醌容易水解成相应的羟基衍生物。母体化合物5，8-喹啉醌在无水条件下仅在6，8-位上与氯化氢加成生成6-氯-5，8-二羟基喹啉，5，8-喹啉醌的几种衍生物在初步试验中显示出显著的杀阿米巴活性。其中最有效的是7-十一烷基-6-羟基-5，8-喹啉醌（I）。3由于众所周知的杀阿米巴剂--灭幼脲和Diodoquin是卤代喹啉，因此研究其活性是令人感兴趣的。
6-Chloro-and 7-chloro-5, 8-quinolinequinone (II and III) were prepared and aryl groups were introduced at the unsub-stituted positions of the quinone rings by reaction with diazonium salts; alkyl groups were introduced by peroxide alkylation. The 7-aryl-6-chloro-and 6-aryl-7-chloro-5, 8-quinolinequiuones were readily hydrolyzed to the corresponding hydroxyl derivatives. The parent compound, 5, 8-quinolinequinone, adds hydrogen chloride at the 6, 8-positions exclusively to yield 6-chloro-5, 8-dihydroxyquinoline under anhydrous conditions.Several of thederivatives of 5, 8-quinolinequi-none2 described in precedingpapers ofthis series have displayedsignificant amebicidal activity in preliminary tests. One of the most effective of these was 7-undecyl-6-hydroxy-5, 8-quinolinequi-none (I). 3 Since the well-known amebicides-orm and Diodoquin are halogenated quinolines, it was of interest to investigate the activity of