Synthesis of Biotinylated Galiellalactone Analogues

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
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

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