Design and synthesis of benzofuran‐ and naphthalene‐fused thiazinones as antimycobacterial agents

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Abstract: Benzothiazinones (BTZs) have widely inspired medicinal chemistry and translational research due to their remarkable antitubercular potency and clinical potential. While most structure–activity relationship campaigns have largely focused on lateral chain modifications and substituents on the BTZ core, scaffold hopping strategies have been rarely investigated previously. In this work, we report the first example of ring expansion of the BTZ core toward benzofuran‐ and naphthalene‐fused thiazinones. In vitro testing showed micromolar activity for both compounds, and molecular docking simulations provided insights into their reduced inhibitory capacity toward the enzymatic target (DprE1). Calculated electrochemical potentials revealed a lower susceptibility to reduction as opposed to BTZ drug candidates, in line with the mechanistic requirement for covalent binding.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Design and synthesis of benzofuran‐ and naphthalene‐fused thiazinones as antimycobacterial agents ; day:04 ; month:09 ; year:2023 ; extent:11
Archiv der Pharmazie ; (04.09.2023) (gesamt 11)

Creator: Keiff, François
Jacques dit Lapierre, Thibault J. W.
Bernal, Freddy Alexander
Kloss, Florian

DOI: 10.1002/ardp.202300356

URN: urn:nbn:de:101:1-2023090515165522596556

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 10:59 AM CEST

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Keiff, François
Jacques dit Lapierre, Thibault J. W.
Bernal, Freddy Alexander
Kloss, Florian

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Design and synthesis of benzofuran‐ and naphthalene‐fused thiazinones as antimycobacterial agents

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Other Objects (12)

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