Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds
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Date
2021-02
Journal Title
Journal ISSN
Volume Title
Publisher
Royal Society of Chemistry
Abstract
The formation efficiency of hydride-induced Meisenheimer complexes of nitroaromatic compounds is consistent with their anti-TB activities exemplied by MDL860 and benzothiazol N-oxide (BTO) analogs. Herein we report that nitro cyano phenoxybenzenes (MDL860 and analogs) reacted slowly and incompletely which reflected their moderate anti-TB activity, in contrast to the instantaneous reaction of BTO derivatives to quantitatively generate Meisenheimer complexes which corresponded to their enhanced anti-TB activity. These results were corroborated by mycobacterial and radiolabelling studies that confirmed inhibition of the DprE1 enzyme by BTO derivatives but not MDL860 analogs.
Description
Keywords
hydride compounds
Citation
Liu, Rui, Lowell Markley, Patricia A. Miller, Scott Franzblau, Gauri Shetye, Rui Ma, Karin Savková et al. "Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds." RSC medicinal chemistry 12, no. 1 (2021): 62-72.