Journal
JOURNAL OF MEDICINAL CHEMISTRY
Volume 52, Issue 20, Pages 6217-6223Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jm900544z
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Funding
- CICYT [BQU 2006-03794]
- Generalitat de Catalunya
- Barcelona Science Park
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The first total synthesis of the indole alkaloids (+/-)-aplicyanins A, B, and E, plus 17 analogues, all in racemic form, is reported. Modifications to the parent compound included changing the number of bromine substituents on the indole, the nature of the substituents on the indole nitrogen (H, Me, or OMe), and/or the oxidation level of the heterocyclic core tetrahydropyrimidine. Each compound was screened against three human tumor cell lines, and 14 of the newly synthesized compounds showed considerable cytotoxicity. The assay results were used to establish structure-activity relationships. These results suggest that the presence of the bromine at position 5 of the indole is critical to activity, as well as the acetyl group on the imine nitrogen does in some compounds.
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