The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils.
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Cadiolide analogues and their precursors as new inhibitors of bacterial quorum sensing and biofilm formation.
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Department of Biomedical and Chemical Engineering, Civil and Environmental Engineering, and Biology, Syracuse University, Syracuse, NY 13244, USA. Electronic address:
Bacterial quorum sensing (QS) and biofilm formation are promising targets for developing new therapies to treat chronic infections. Herein, we report the stereoselective synthesis of 18 new analogs of natural cadiolides. Among the new compounds, substances 8b, 8f, 8i, 9a, 9b and 9e completely inhibited the biofilm formation of Escherichia coli RP347 in vitro.
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School of Chemical and Physical Sciences, and Centre for Biodiscovery, Victoria University of Wellington, Wellington 6012, New Zealand.
Marine invertebrates, especially tunicates, are a lucrative resource for the discovery of new lead compounds for the development of clinically utilized drugs. This review describes the isolation, synthesis and biological activities of several classes of marine-derived butenolide natural products, namely rubrolides and related cadiolides and prunolides. All relevant studies pertaining to these compounds up to the end of 2019 are included.
View Article and Find Full Text PDFCadiolides J-M, antibacterial polyphenyl butenolides from the Korean tunicate Pseudodistoma antinboja.
Bioorg Med Chem Lett
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Center for Marine Natural Products and Drug Discovery, School of Earth and Environmental Sciences, Seoul National University, NS-80, Seoul 08826, Republic of Korea; Research Institute of Oceanography, Seoul National University, NS-80, Seoul 08826, Republic of Korea. Electronic address:
Activity-guided fractionations of the tunicate Pseudodistoma antinboja yielded four new compounds of the cadiolide class (cadiolides J-M, 1, 3-5) along with a known one (cadiolide H, 2). The structures were defined by spectroscopic methods including X-ray crystallographic analysis. These compounds were evaluated for their antibacterial activity and exhibited potent antibacterial activity against all of the drug resistant strains tested with MICs comparable to those of marketed drugs such as vancomycin and linezolid.
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Bioorg Med Chem
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Normandie Univ, COBRA, UMR 6014 et FR 3038, CNRS, Univ Rouen, INSA Rouen, 1 rue Tesnières, 76821 Mont-Saint-Aignan, Cedex, France. Electronic address:
The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils.
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Département de Chimie, Université Laval, Pavillon Alexandre-Vachon, 1045 Avenue de la Médecine, Quebec City, Quebec G1V 0A6, Canada.
A concise, modular and efficient synthesis of the title natural products is reported. Prominent steps include (i) one-pot assembly of a key β-aryl-α-benzoylbutenolide building block by regiocontrolled "click-unclick" oxazole-ynone Diels-Alder cycloaddition/cycloreversion and ensuing 2-alkoxyfuran hydrolysis and (ii) a protecting group-free vinylogous Knoevenagel condensation enabling rapid access to cadiolides A, B, and D from a common precursor.
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