Regio- and diastereoselective synthesis of spiropyrroloquinoxaline grafted indole heterocyclic hybrids and evaluation of their anti- Mycobacterium tuberculosis activity

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...

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Bibliographic Details
Published in:RSC advances 2020-06, Vol.10 (40), p.23522-23531
Main Authors: 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
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemistry
Crystallography
Cycloaddition
Stereoselectivity
Tryptophan
Tuberculosis
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Summary: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.
ISSN:2046-2069
2046-2069
DOI:10.1039/d0ra02525a