Synthesis and Cytotoxic Activity of a Small Naphthoquinone Library: First Synthesis of Juglonbutin

Brötz, Elke, Herrmann, Jennifer, Wiese, Jutta, Zinecker, Heidi, Maier, Armin, Kelter, Gerhardt, Imhoff, Johannes F., Müller, Rolf and Paululat, Thomas (2014) Synthesis and Cytotoxic Activity of a Small Naphthoquinone Library: First Synthesis of Juglonbutin European Journal of Organic Chemistry, 2014 (24). pp. 5318-5330. DOI 10.1002/ejoc.201402272.

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Abstract

A synthetic protocol has been designed to synthesize grecoketidone (2k), 5-hydroxylapachol (2g), and the recently discovered natural products juglonbutin (2o) and its derivatives, leading to a small library of different 1,4-naphthoquinones with the intention of finding new active compounds. Within our collection, 2-O-alkylated naphthoquinones with an ester functionality in the side-chain and a free OH group at C-5 showed the best activities. Compounds 2f, 2m, and 2n showed GI50 values against 12 tumor cell lines in the lower micromolar range and juglonbutin (2o) showed remarkably efficient inhibition of the glycogen synthase kinase 3β with an IC50 value of 2.03 μM. Furthermore, studies on the mode of action of the most active cytotoxic compounds have been carried out. To the best of our knowledge, this is the first report on the synthesis of juglonbutin (2o) and its biological activity.

Document Type: Article
Additional Information: WOS:000340525300019
Keywords: Natural products; Quinones; Medicinal chemistry; Toxicity; Antitumor agents
Research affiliation: OceanRep > GEOMAR > FB3 Marine Ecology > FB3-MI Marine Microbiology
OceanRep > GEOMAR > Applied R&D > Centre for Marine Substances (KiWiZ)
OceanRep > The Future Ocean - Cluster of Excellence
Refereed: Yes
DOI etc.: 10.1002/ejoc.201402272
ISSN: 1434-193X
Projects: KIWIZ, Future Ocean
Date Deposited: 19 Aug 2014 12:12
Last Modified: 04 Jan 2017 12:32
URI: http://eprints.uni-kiel.de/id/eprint/25472

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