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

Madikizela, B., Eckhardt, T., Goddard, R., Richter, A., Lins, A., Lehmann, C., et al. (2021). Synthesis, structural characterization and antimycobacterial evaluation of several halogenated non-nitro benzothiazinones. Medicinal Chemistry Research, 30(8), 1523-1533. doi:10.1007/s00044-021-02735-4.

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 Creators:
Madikizela, Balungile1, 2, Author
Eckhardt, Tamira1, Author
Goddard, Richard3, Author           
Richter, Adrian1, 4, Author
Lins, Anika1, Author
Lehmann, Christoph1, Author
Imming, Peter1, Author
Seidel, Rüdiger W.1, Author
Affiliations:
1Institut für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, Halle (Saale) 06120, Germany, ou_persistent22              
2Phytomedicine Programme, Department of Paraclinical Sciences, University of Pretoria, Private Bag X04, Onderstepoort 0110, South Africa, ou_persistent22              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              
4Department of Medicine and Department of Microbiology and Immunology, University of British Columbia, Vancouver, BC V6T 1Z3, Canada, ou_persistent22              

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Free keywords: Benzothiazinones; Tuberculosis; Antimycobacterial evaluation; in vitro activity; Synthesis; Crystal structure
 Abstract: 8-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.

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Language(s): eng - English
 Dates: 2021-03-312021-06-102021-08-01
 Publication Status: Published in print
 Pages: 11
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1007/s00044-021-02735-4
 Degree: -

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Title: Medicinal Chemistry Research
  Abbreviation : Med. Chem. Res.
Source Genre: Journal
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Publ. Info: New York : Springer
Pages: - Volume / Issue: 30 (8) Sequence Number: - Start / End Page: 1523 - 1533 Identifier: ISSN: 1054-2523
CoNE: https://pure.mpg.de/cone/journals/resource/1054-2523