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Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue

Year: 2012

Type: article

Abstract: The first synthesis of a lactam analogue 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.

Source: Organic & Biomolecular Chemistry

DOI: 10.1039/c2ob26649k

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

Institutions: RMIT University, The University of Melbourne, Walter and Eliza Hall Institute of Medical Research

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Good health and well-being

Open Access status: green

OpenAlex ID: W2158484073

FWCI: 0.588

Cites: 42

Cited by: 10

Related to: 10