一种简洁的硅基胺方法用于合成具有强效体内抗疟活性的 2-氨基-3-羟基吲哚。
A concise silylamine approach to 2-amino-3-hydroxy-indoles with potent in vivo antimalaria activity.
机构信息
Infectious Disease Initiative Program, The Broad Institute of Harvard and MIT, 7 Cambridge Center, Cambridge, Massachusetts 02142, USA.
出版信息
Org Lett. 2010 Sep 17;12(18):3998-4001. doi: 10.1021/ol101566h.
Abstract
The development of a concise strategy to access 2-amino-3-hydroxy-indoles, which are disclosed as novel antimalarials with potent in vivo activity, is reported. Starting from isatins the target compounds are synthesized in 2 steps and in good yields via oxoindole intermediates by employing tert-butyldimethylsilyl amine (TBDMSNH(2)) as previously unexplored ammonia equivalent.
摘要
本文报道了一种简洁的策略来合成 2-氨基-3-羟基吲哚，这些化合物被揭示为具有强效体内活性的新型抗疟药物。以色胺酮为起始原料，通过使用叔丁基二甲基硅基胺（TBDMSNH（2））作为以前未探索的氨等价物，经氧吲哚中间体两步反应以良好的收率合成目标化合物。
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2
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3
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4
In vitro evaluations of antimalarial drugs and their relevance to clinical outcomes.抗疟药物的体外评估及其与临床结果的相关性。
Int J Parasitol. 2008 Jun;38(7):743-7. doi: 10.1016/j.ijpara.2008.03.004. Epub 2008 Apr 1.
5
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J Org Chem. 2007 Aug 3;72(16):6298-300. doi: 10.1021/jo070553t. Epub 2007 Jul 11.
6
High-throughput Plasmodium falciparum growth assay for malaria drug discovery.用于疟疾药物发现的高通量恶性疟原虫生长测定法。
Antimicrob Agents Chemother. 2007 Feb;51(2):716-23. doi: 10.1128/AAC.01144-06. Epub 2006 Nov 20.
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