Arumugam Natarajan, Almansour Abdulrahman I, Kumar Raju Suresh, Mohammad Ali Al-Aizari Abdul Jaleel, Alaqeel Shatha Ibrahim, Kansız Sevgi, Krishna Vagolu Siva, Sriram Dharmarajan, Dege Necmi
Department of Chemistry, College of Science, King Saud University P.O Box 2455 Riyadh 11451 Saudi Arabia
Department of Chemistry, College of Science, King Saud University (034) Riyadh 11495 Saudi Arabia.
RSC Adv. 2020 Jun 19;10(40):23522-23531. doi: 10.1039/d0ra02525a.
An efficient and eco compatible approach for the regio- and stereoselective synthesis of structurally diverse novel hybrid heterocycles comprising spiropyrrolidine, indenoquinoxaline and indole structural units in excellent yields, has been achieved through a one-pot multicomponent process involving 1,3-dipolar cycloaddition as a key step. The 1,3-dipolar component is the azomethine ylide generated from indenoquinoxaline and l-tryptophan and reacts with various substituted β-nitrostyrenes affording the spiroheterocyclic hybrids. The ring system thus created possesses two C-C and three C-N bonds and four adjacent stereogenic carbons, one of which is quaternary and the reaction proceeded with full diastereomeric control. All the synthesized compounds were assayed for their activity against H37Rv using MABA assay. Interestingly, the compound bearing a 2-fluoro substituent on the aryl ring displayed an equipotent activity (MIC 1.56 μg mL) to ethambutol against H37Rv.
通过一锅多组分反应，以1,3-偶极环加成作为关键步骤，实现了一种高效且环境友好的方法，用于区域和立体选择性合成结构多样的新型杂化杂环化合物，这些化合物包含螺吡咯烷、茚并喹喔啉和吲哚结构单元，产率优异。1,3-偶极组分是由茚并喹喔啉和L-色氨酸生成的甲亚胺叶立德，它与各种取代的β-硝基苯乙烯反应，得到螺杂环杂化物。由此形成的环系具有两个C-C键和三个C-N键以及四个相邻的立体ogenic碳，其中一个是季碳，反应以完全的非对映体控制进行。所有合成的化合物都使用MABA测定法测定了它们对H37Rv的活性。有趣的是，芳环上带有2-氟取代基的化合物对H37Rv显示出与乙胺丁醇相当的活性（MIC为1.56μg/mL）。
