Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds?
RSC Medicinal Chemistry Pub Date: 2021-01-04 DOI: 10.1039/D0MD00390E
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.
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Journal Name：RSC Medicinal Chemistry
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CAS no.: 89640-58-4
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