Expanding indole diversity: direct 1-step synthesis of 1,2-fused indoles and spiroindolines from 2-halo anilines for fast SAR antiviral elucidation against tobacco mosaic virus (TMV)
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- 作者：Linwei Chen ; Yongxian Liu ; Hongjian Song ; Yuxiu Liu ; Lizhong Wang…
- 关键词：Pseudo ; indole alkaloids ; 1 ; 2 ; Fused indole ; Spiroindoline ; Tobacco mosaic virus ; Anti ; TMV
- 刊名：Molecular Diversity
- 出版年：2017
- 出版时间：February 2017
- 年：2017
- 卷：21
- 期：1
- 页码：61-68
- 全文大小：
- 刊物类别：Chemistry and Materials Science
- 刊物主题：Biochemistry, general; Organic Chemistry; Polymer Sciences; Pharmacy;
- 出版者：Springer International Publishing
- ISSN：1573-501X
- 卷排序：21
文摘
To systematically investigate the influence of the variation of the original skeletons and spatial configuration of 2,3-fused indole natural products on antiviral activities, two types of structurally novel and potent pseudo-indole natural product derivatives, 1,2-fused indole and spiroindoline, with different substituents were direct synthesized from 2-halo anilines, and their antiviral activities against tobacco mosaic virus (TMV) were evaluated. The results showed that these compounds exhibited good anti-TMV activity, especially 3f, 3g, 3i, 5e, 5h, and 5l, which were more potent than the commercial anti-virus agent ribavirin. An SAR investigation demonstrates that the original ring size, arrangement, and planarity are not optimal; their anti-TMV activities can be improved by skeleton modification and spatial configuration variation. Both of the structurally novel skeletons provide a new template for antiviral studies, which may also provide some useful information for antiviral mechanism elucidation.