Number of the records: 1
The Biomimetic Synthesis of Polyarylated Fluorenes, Relevant to Selaginellaceae Polyphenols, Leading to the Spontaneous Formation of Stable Radicals
- 1.
SYSNO ASEP 0583092 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title The Biomimetic Synthesis of Polyarylated Fluorenes, Relevant to Selaginellaceae Polyphenols, Leading to the Spontaneous Formation of Stable Radicals Author(s) Nallappan, S. (CZ)
Lapinskaite, R. (CZ)
Hájíček, J. (CZ)
Kunák, D. (CZ)
Čambal, P. (CZ)
Nečas, D. (CZ)
Císařová, I. (CZ)
Atalay, H. N. (TR)
Tumer, T. B. (TR)
Tarábek, Ján (UOCHB-X) RID, ORCID
Schwarzová-Pecková, K. (CZ)
Rycek, L. (CZ)Article number e202300410 Source Title ChemPlusChem. - : Wiley - ISSN 2192-6506
Roč. 89, č. 4 (2024)Number of pages 9 s. Language eng - English Country US - United States Keywords selaginellacea polyphenols ; biomimetic synthesis ; radicals ; spin density distribution ; cytotoxicity Method of publishing Open access Institutional support UOCHB-X - RVO:61388963 UT WOS 001110088900001 EID SCOPUS 85177886399 DOI 10.1002/cplu.202300410 Annotation This work reports a biomimetic synthesis of polyarylated fluorene derivatives. The molecules are formed via intramolecular electrophilic aromatic substitution, resembling a cyclization leading towards the natural selaginpulvilins from selaginellins. The scope of the reaction was investigated, and the products were obtained in 60-95 % yields. Some of the compounds decompose to a stable radical. We investigated the nature and the origin of the radical using experimental methods, including EPR or electrochemical measurements, as well as theoretical methods, such as DFT calculations. Based on our observations, we hypothesize, that phenoxy radicals are formed in the first instance, which however undergo internal rearrangement to thermodynamically more stable carbon-centered radicals. The preliminary data also show the cytotoxic properties of some of the molecules. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2025 Electronic address https://doi.org/10.1002/cplu.202300410
Number of the records: 1