Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective

• Yaroslav D. Boyko,
• Valentin S. Dorokhov,
• Alexey Yu. Sukhorukov and
• Sema L. Ioffe

Beilstein J. Org. Chem. 2017, 13, 2214–2234, doi:10.3762/bjoc.13.220

• organic solvent phase. The described method of oximinoalkylation of the С-3 position of indoles has a great potential for the synthesis of pharmaceutically relevant compounds and natural products. Thus, de Lera and co-workers described the synthesis of indole-derived psammaplin A analogue 72, which

• acid 74, which was then used in a double amidation with cystamine to give the target compound 72 after unmasking of oxime. A series of other psammaplin A analogs were prepared in a similar manner. Reduction of the oxime group in oximinoalkylated indoles provides a direct access to various substituted

• NSA14 to electron-rich arenes. Addition of nitrosoalkenes NSA14 to pyrroles and indoles. Reaction of phosphinyl nitrosoalkenes NSA15 with indole. Reaction of pyrrole with α,α’-dihalooximes 70. Synthesis of indole-derived psammaplin A analogue 72. Synthesis of tryptophanes by reduction of

Thioester derivatives of the natural product psammaplin A as potent histone deacetylase inhibitors

• Matthias G. J. Baud,
• Thomas Leiser,
• Vanessa Petrucci,
• Mekala Gunaratnam,
• Stephen Neidle,
• Franz-Josef Meyer-Almes and
• Matthew J. Fuchter

Beilstein J. Org. Chem. 2013, 9, 81–88, doi:10.3762/bjoc.9.11

• , Schnittspahnstraβe 12, 64287 Darmstadt, Germany Cancer Research UK Biomolecular Structure Group, UCL School of Pharmacy, 29-39 Brunswick Square, London WC1N 1AX, United Kingdom 10.3762/bjoc.9.11 Abstract There has been significant interest in the bioactivity of the natural product psammaplin A, most recently as a

• potent and isoform selective HDAC inhibitor. Here we report our preliminary studies on thioester HDAC inhibitors derived from the active monomeric (thiol) form of psammaplin A, as a means to improve compound delivery into cells. We have discovered that such compounds exhibit both potent cytotoxicity and

• . Keywords: epigenetics; histone deacetylase; natural product; prodrug; psammaplin A; thioester; Introduction Chromatin is a macromolecular complex consisting of DNA, histone and nonhistone proteins. The epigenetic control of chromatin organization plays a major role in the regulation of gene expression