Design of non-cytotoxic 6,7-dihydroxycoumarin-5-carboxylates with antibiofilm activity against Staphylococcus aureus and Candida albicans

Robert Zscherp; Aishi Chakrabarti; Anna P. Lehmann; Hedda Schrey; Hoaxuan Zeng; Wera Collisi; Philipp Klahn

doi:10.1039/D3OB00303E

Design of non-cytotoxic 6,7-dihydroxycoumarin-5-carboxylates with antibiofilm activity against Staphylococcus aureus and Candida albicans†

Robert Zscherp,‡^ab Aishi Chakrabarti,

‡^cd Anna P. Lehmann,

^ab Hedda Schrey,^ef Hoaxuan Zeng,^ef Wera Collisi^ef and Philipp Klahn

*^bcd

Author affiliations

* Corresponding authors

^a Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany

^b Laboratories of Natural Product and Conjugation Chemistry (naconLabs) – A Technology Transfer Center of iTUBS mbH, Wilhelmsgarten 3, 38100 Braunschweig, Germany
E-mail: Philipp.Klahn@gu.se

^c Division of Organic and Medicinal Chemistry, Department of Chemistry and Molecular Biology, University of Gothenburg, Kemigården 4, 41296 Göteborg, Sweden

^d Centre for Antibiotic Resistance Research in Gothenburg (CARe), Sweden

^e Department of Microbial Drugs, Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig, Germany

^f German Centre for Infection Research (DZIF), Partner Site Hannover-Braunschweig, 38124 Braunschweig, Germany

Abstract

The 6,7-dihydroxycoumarin-5-carboxylates DHCou and 4-Me-DHCou have been synthesized via five-step route including a propargyl-Claisen rearrangement as key step. The compounds show antibiofilm activity against Stapylococcus aureus and Candida albicans but lack the cytotoxic activity of parent 6,7-dihydroxycoumarines such as esculetin and 4-methylesculetin.

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DOI: https://doi.org/10.1039/D3OB00303E
Article type: Communication
Submitted: 23 Feb 2023
Accepted: 05 Apr 2023
First published: 06 Apr 2023
This article is Open Access

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Org. Biomol. Chem., 2023,21, 4744-4749

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Design of non-cytotoxic 6,7-dihydroxycoumarin-5-carboxylates with antibiofilm activity against Staphylococcus aureus and Candida albicans

R. Zscherp, A. Chakrabarti, A. P. Lehmann, H. Schrey, H. Zeng, W. Collisi and P. Klahn, Org. Biomol. Chem., 2023, 21, 4744 DOI: 10.1039/D3OB00303E

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Organic & Biomolecular Chemistry

Design of non-cytotoxic 6,7-dihydroxycoumarin-5-carboxylates with antibiofilm activity against Staphylococcus aureus and Candida albicans†

Abstract

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Design of non-cytotoxic 6,7-dihydroxycoumarin-5-carboxylates with antibiofilm activity against Staphylococcus aureus and Candida albicans

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