Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue

Dan Balan; Christopher J. Burns; Nicholas G. Fisk; Helmut Hügel; David C. S. Huang; David Segal; Charlotte White; Jörg Wagler; Mark A. Rizzacasa

doi:10.1039/C2OB26649K

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Organic & Biomolecular Chemistry

Issue 40, 2012

The international home of synthetic, physical and biomolecular organic chemistry.

Impact Factor 3.696 48 Issues per Year Indexed in MEDLINE

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Paper

Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue

Dan Balan,^a Christopher J. Burns,^b^c Nicholas G. Fisk,^d Helmut Hügel,*^a David C. S. Huang,^b^c David Segal,^b^c Charlotte White,^d Jörg Wagler^a and Mark A. Rizzacasa*^d

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Corresponding authors

School of Applied Sciences [Applied Chemistry], RMIT University, Bowen Street, Melbourne, Australia

Walter and Eliza Hall Institute of Medical Research, 1G Royal Parade, Parkville, Australia

Department of Medical Biology, The University of Melbourne, Parkville, Australia

School of Chemistry, the Bio21 Institute, The University of Melbourne, Australia
E-mail: masr@unimelb.edu.au

Org. Biomol. Chem., 2012,10, 8147-8153

DOI: 10.1039/C2OB26649K
Received 15 Jun 2012, Accepted 24 Aug 2012
First published online 28 Aug 2012

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The first synthesis of a lactam analogue 3 of salicylihalamide A (1) is reported. A key step in the approach was a photochemical acylation coupling between amine 10 and dioxinone 9 to form the amide 19. Acetylation followed by RCM with Grubbs 1st generation catalyst gave the desired E-lactam 23 (E:Z ratio 87:13) as the major compound. Conversion of macrolactam 23 into the vinyl iodide 26 followed by Cu catalysed cross coupling with the diene amide 7 gave aza-salicylihalamide analogue 3 in good yield. This compound demonstrated potent activity against several human leukaemia cell lines.