Total Synthesis and Biological Evaluation of the Anti-Inflammatory (13R,14S,15R)-13-Hydroxy-14-deoxyoxacyclododecindione
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Kevin Seipp
- Jonathan Gross
- Anna Maria Kiefer
- Gerhard Erkel
- Till Opatz
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000983234000001&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1021/acs.jnatprod.2c01145
- eISSN
- 1520-6025
- Externe Identifier
- Clarivate Analytics Document Solution ID: F6DQ7
- PubMed Identifier: 37001011
- ISSN
- 0163-3864
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- JOURNAL OF NATURAL PRODUCTS
- Paginierung
- 924 - 938
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Titel
- Total Synthesis and Biological Evaluation of the Anti-Inflammatory (13R,14S,15R)-13-Hydroxy-14-deoxyoxacyclododecindione
- Sub types
- Article
- Ausgabe der Zeitschrift
- 86
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Autoren
- Kevin Seipp
- Jonathan Groß
- Anna Maria Kiefer
- Gerhard Erkel
- Till Opatz
- DOI
- 10.1021/acs.jnatprod.2c01145
- eISSN
- 1520-6025
- ISSN
- 0163-3864
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- Journal of Natural Products
- Sprache
- en
- Online publication date
- 2023
- Paginierung
- 924 - 938
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/acs.jnatprod.2c01145
- Datum der Datenerfassung
- 2023
- Titel
- Total Synthesis and Biological Evaluation of the Anti-Inflammatory (13<i>R</i>,14<i>S</i>,15<i>R</i>)-13-Hydroxy-14-deoxyoxacyclododecindione
- Ausgabe der Zeitschrift
- 86
Datenquelle: Crossref
- Abstract
- The first total synthesis of the natural product (13<i>R</i>,14<i>S</i>,15<i>R</i>)-13-hydroxy-14-deoxyoxacyclododecindione, which was isolated in 2018 as a member of the oxacyclododecindione family, is reported. A synthetic strategy through intramolecular Friedel-Crafts acylation combined with the stereoselective synthesis of a new triol key fragment allowed the preparation of the macrolactone. Due to mismatching physical data of the synthetic product, a revision of the configuration of the natural product isolated in 2018 is required. Light-induced <i>E</i>/<i>Z</i>-isomerism of the macrolactone backbone is described for the first time in the class of oxacyclododecindione-type macrolactones. The hydroxylated macrolactone prepared herein was found to show highly promising IC<sub>50</sub> values in biological assays addressing the inhibition of inflammatory responses.
- Addresses
- Department of Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany.
- Autoren
- Kevin Seipp
- Jonathan Groß
- Anna Maria Kiefer
- Gerhard Erkel
- Till Opatz
- DOI
- 10.1021/acs.jnatprod.2c01145
- eISSN
- 1520-6025
- Externe Identifier
- PubMed Identifier: 37001011
- Funding acknowledgements
- Ministerium f?r Wissenschaft und Gesundheit Rhineland-Palatinate:
- Open access
- false
- ISSN
- 0163-3864
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- Journal of natural products
- Schlüsselwörter
- Anti-Inflammatory Agents
- Molecular Structure
- Isomerism
- Stereoisomerism
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2023
- Paginierung
- 924 - 938
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Datum der Datenerfassung
- 2023
- Titel
- Total Synthesis and Biological Evaluation of the Anti-Inflammatory (13<i>R</i>,14<i>S</i>,15<i>R</i>)-13-Hydroxy-14-deoxyoxacyclododecindione.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 86
Datenquelle: Europe PubMed Central
- Abstract
- The first total synthesis of the natural product (13R,14S,15R)-13-hydroxy-14-deoxyoxacyclododecindione, which was isolated in 2018 as a member of the oxacyclododecindione family, is reported. A synthetic strategy through intramolecular Friedel-Crafts acylation combined with the stereoselective synthesis of a new triol key fragment allowed the preparation of the macrolactone. Due to mismatching physical data of the synthetic product, a revision of the configuration of the natural product isolated in 2018 is required. Light-induced E/Z-isomerism of the macrolactone backbone is described for the first time in the class of oxacyclododecindione-type macrolactones. The hydroxylated macrolactone prepared herein was found to show highly promising IC50 values in biological assays addressing the inhibition of inflammatory responses.
- Autoren
- Kevin Seipp
- Jonathan Groß
- Anna Maria Kiefer
- Gerhard Erkel
- Till Opatz
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/37001011
- DOI
- 10.1021/acs.jnatprod.2c01145
- eISSN
- 1520-6025
- Ausgabe der Veröffentlichung
- 4
- Zeitschrift
- J Nat Prod
- Schlüsselwörter
- Anti-Inflammatory Agents
- Isomerism
- Molecular Structure
- Stereoisomerism
- Sprache
- eng
- Country
- United States
- Paginierung
- 924 - 938
- Datum der Veröffentlichung
- 2023
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2024
- Titel
- Total Synthesis and Biological Evaluation of the Anti-Inflammatory (13R,14S,15R)-13-Hydroxy-14-deoxyoxacyclododecindione.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 86
Datenquelle: PubMed
- Autoren
- Kevin Seipp
- Jonathan Groß
- Anna Maria Kiefer
- Gerhard Erkel
- Till Opatz
- DOI
- 10.1021/acs.jnatprod.2c01145
- eISSN
- 1520-6025
- ISSN
- 0163-3864
- Zeitschrift
- Journal of Natural Products
- Sprache
- en
- Online publication date
- 2023
- Status
- Published online
- Herausgeber
- American Chemical Society (ACS)
- Herausgeber URL
- http://dx.doi.org/10.1021/acs.jnatprod.2c01145
- Datum der Datenerfassung
- 2023
- Titel
- Total Synthesis and Biological Evaluation of the Anti-Inflammatory (13R,14S,15R)-13-Hydroxy-14-deoxyoxacyclododecindione
Datenquelle: Manual
- Beziehungen:
- Eigentum von