A stereo,regioselective synthesis and discovery of antimycobaterium tuberculosis activity of novel β-lactam grafted spirooxindolopyrrolidine hybrid heterocycles |
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| Authors: | Natarajan Arumugam Abdulrahman I Almansour Raju Suresh Kumar Vagolu Siva Krishna Dharmarajan Sriram Ramanathan Padmanaban |
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| Institution: | 1. Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia;2. Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500078, Telangana, India;3. Department of Chemistry, School of Physical, Chemical & Applied Sciences, Pondicherry University, R.V. Nagar, Kalapet, Puducherry 605 014, India |
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| Abstract: | A stereo- and regioselective synthesis of hitherto unexplored novel class of β-lactam embedded spirooxindolopyrrolidine hybrid heterocycles have been accomplished via ionic liquid accelerated 3 + 2]-cycloaddition reaction process. The expected unusual lactonization/lactamization product could not be observed even in traces. The in vitro antimycobacterium tubercular activity of the synthesized spiroheterocyclic hybrids were assessed against Mycobacterium tuberculosis H37Rv. Among them, the compounds with no substitution and chlorosubstitution on the oxindole ring showed the most potent activity with a MIC 0.78 μg/mL and 1.56 μg/mL, respectively which were two-fold and equal activity than the standard drug, ethambutol (MIC = 1.56 μg/mL). |
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| Keywords: | Spirooxindolopyrrolidines β-lactam 1 3-Dipolar cycloaddition reaction Ionic liquids DFT study |
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