- Controllable synthesis of pyrido[2,3-: b] indol-4-ones or indolo[3,2- b] quinolines via formal intramolecular C(sp2)-H functionalization
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A novel Fe-catalyzed protocol for the controllable synthesis of pyrido[2,3-b]indol-4-ones or indolo[3,2-b]quinolines has been developed by using indole-2-carboxylic derivatives as starting materials. Indole-2-carboxenamines were transformed into pyrido[2,3-b]indol-4-ones through intramolecular N-H/C-H coupling, in which a carbonyl 1,2-migration was involved. Whereas, when indole-2-carboxarylamines were employed, indolo[3,2-b]quinolones were produced through direct N-H/C-H coupling. The desired products were obtained under mild reaction conditions in moderate to good yields with wide substrate scope. The natural product quindolinone was conveniently prepared by this reaction.
- Song, Bo,Wang, Mengdan,Xu, Murong,Kong, Lingkai,Xie, Huihui,Wang, Chengyu,Li, Yanzhong
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supporting information
p. 9960 - 9965
(2019/12/06)
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- Structure-activity relationship of indoloquinoline analogs anti-MRSA
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Indolo[3,2-b]quinoline analogs (3a-3s), 4-(acridin-9-ylamino) phenol hydrochloride (4), benzofuro[3,2-b]quinoline (3t), indeno[1,2-b]quinolines (3u and 3v) have been synthesized. Those compounds were found to exhibit anti-bacterial activity towards Methicillin-resistant Staphylococcus aureus (anti-MRSA activity). Structure-activity relationship studies were conducted that indoloquinoline ring, benzofuroquinoline ring and 4-aminophenol group are essential structure for anti-MRSA activity.
- Zhao, Min,Kamada, Tomonori,Takeuchi, Aya,Nishioka, Hiromi,Kuroda, Teruo,Takeuchi, Yasuo
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p. 5551 - 5554
(2015/11/17)
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- Anti-malaria active 10-H-indolo[3,2-b]quinoline-11-yl-amines. Part 1: Phenol-Mannich-bases of the amodiaquine and cycloquine type
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The 11-chloro-quindoline derivatives 3 react with 4-aminophenol and the mono- and bis-phenol-Mannich-bases 6 to yield the 10 H-indolo[3,2-b]quinoline-11-ylamines 4 and 7. The amodiaquine analogue 7a as the best of all compounds shows a comparable activity with choroquine and inhibits a multiresistant Plasmodium falciparum strain at the same concentration. Compound 7e from the cycloquine-type was selected for an in vivo antitumor screening programme.
- Gorlitzer,Stockmann,Walter
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p. 231 - 235
(2007/10/02)
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