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Benzodioxane-Benzamides as FtsZ Inhibitors: Effects of Linker's Functionalization on Gram-Positive Antimicrobial
Lorenzo Suigo1, William Margolin2, Eugenia Ulzurrun3,4
1Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via Luigi Mangiagalli, 25, 20133 Milano, Italy.
Antibiotics (Basel, Switzerland)
|December 23, 2023
Summary
Researchers explored modifications to benzodioxane-benzamide antimicrobials targeting bacterial FtsZ. Introducing a hydroxy group on the linker altered activity and created stereoisomers, offering potential for prodrug development.
Area of Science:
- Microbiology
- Medicinal Chemistry
- Drug Discovery
Background:
- FtsZ is a crucial bacterial protein and a promising antimicrobial target.
- Benzodioxane-benzamides show potential against Gram-positive and Gram-negative bacteria.
- Modifying existing antimicrobial scaffolds can enhance efficacy and properties.
Purpose of the Study:
- To investigate the impact of a substituent on the ethylenic linker of benzodioxane-benzamides.
- To evaluate the antimicrobial activity and pharmacokinetic properties of novel derivatives.
- To explore the role of stereochemistry in antimicrobial efficacy.
Main Methods:
- Synthesis of benzodioxane-benzamide derivatives with linker substituents.
- Isolation and characterization of erythro and threo stereoisomers.
- Antimicrobial activity assays and pharmacokinetic property evaluation.
Main Results:
- The hydroxy group substituent showed a modest effect on antimicrobial activity.
- The substitution generated a new stereogenic center, yielding distinct isomers.
- The hydroxy group serves as a valuable point for further drug development.
Conclusions:
- Stereochemistry plays a role in the antimicrobial activity of these compounds.
- The modified benzodioxane-benzamides represent a promising class of FtsZ inhibitors.
- The identified hydroxy group is key for developing advanced prodrugs and probes.
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