Escobar, Zilma and Johansson, Martin and Bjartell, Anders and Hellsten, Rebecka and Sterner, Olov (2014) Synthesis of Biotinylated Galiellalactone Analogues. International Journal of Organic Chemistry, 04 (04). pp. 225-235. ISSN 2161-4687
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Abstract
Two biotinylated derivatives of the fungal metabolite galiellalactone (1) were synthesized in order to facilitate the investigation of the molecular mechanism of action of the galiellalactonoids. Galiellalactone is a STAT3-signaling inhibitor that inhibits growth in vitro as well as in vivo of prostate cancer cells expressing activated STAT3. To provide a suitable point of attachment for biotin, the 8-hydroxymethyl derivative (3) and its 7-phenyl analogue 4 were synthesized by a modified tandem Pd-catalysed carbonylation and intramolecular vinyl allene Diels-Alder procedure previously developed. The two primary alcohols obtained, 3 and 4, were coupled to biotin as the 6-aminohexanoic acid amide, activated as the acid chloride, yielding the derivatives 5 and 6.
Item Type: | Article |
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Subjects: | Impact Archive > Chemical Science |
Depositing User: | Managing Editor |
Date Deposited: | 04 Jan 2023 05:40 |
Last Modified: | 25 Jul 2024 07:26 |
URI: | http://research.sdpublishers.net/id/eprint/1390 |