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Synthesis of Biotinylated Galiellalactone Analogues

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DOI: 10.4236/ijoc.2014.44026    2,541 Downloads   3,219 Views   Citations

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.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

Escobar, Z. , Johansson, M. , Bjartell, A. , Hellsten, R. and Sterner, O. (2014) Synthesis of Biotinylated Galiellalactone Analogues. International Journal of Organic Chemistry, 4, 225-235. doi: 10.4236/ijoc.2014.44026.

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