Stereoselective synthesis and discovery of novel spirooxindolopyrrolidine engrafted indandione heterocyclic hybrids as antimycobacterial agents.

[Display omitted] • Novel spirooxindolopyrrolidine tethered indandiones have been synthesized in excellent yields. • A one-pot eco-friendly three component cycloaddition strategy have been employed. • Compounds were assessed for their antimycobacterium activity against Mtb H37Rv. • Compound with chloro substituent displayed two fold activity than that of standard drug, ethambutol. Novel spirooxindolopyrrolidine embedded indandione heterocyclic hybrids were obtained in excellent yields via a regio- and stereoselective one-pot three component reaction between Baylis-Hillman adduct and non-stabilized azomethine ylides. The structure of newly synthesized compounds was elucidated through 1D and 2D spectroscopic data and the stereochemistry was determined by single crystal X-ray diffraction analysis. In vitro tubercular activity against Mycobacterium tuberculosis H37Rv using MABA assay reveals that the compound bearing chlorine substituted on the oxindole ring displayed the most potent activity with MIC 0.78 μg/mL and is two-fold active than the standard drug, ethambutol (MIC 1.56 μg/mL). [ABSTRACT FROM AUTHOR]