Synthesis, structural characterization and antimycobacterial evaluation of several halogenated non-nitro benzothiazinones

Author:

Madikizela BalungileORCID,Eckhardt Tamira,Goddard RichardORCID,Richter AdrianORCID,Lins Anika,Lehmann Christoph,Imming PeterORCID,Seidel Rüdiger W.ORCID

Abstract

Abstract8-Nitro-1,3-benzothiazin-4-ones (BTZs), with BTZ043 and PBTZ169 as the most advanced compounds, represent a new class of potent antitubercular agents, which irreversibly inhibit decaprenylphosphoryl-β-d-ribose-2′-epimerase (DprE1), an enzyme crucial for cell wall synthesis in the pathogen Mycobacterium tuberculosis. Synthesis, structural characterization and in vitro testing against Mycobacterium aurum DSM 43999 and M. tuberculosis H37Rv of halogenated 2-(4-ethoxycarbonylpiperazin-1-yl)-1,3-benzothiazin-4-ones lacking a nitro group are reported. X-ray crystallography reveals that the structure of the BTZ scaffold can significantly deviate from planarity. In contrast to recent reports, the results of the present study indicate that further investigation of halogenated non-nitro BTZs for antitubercular activity is less than a promising approach.

Funder

Deutsche Forschungsgemeinschaft

Publisher

Springer Science and Business Media LLC

Subject

Organic Chemistry,General Pharmacology, Toxicology and Pharmaceutics

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