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Title: Total synthesis and antiproliferative activity screening of (±)-aplicyanins A, B and E and related analogs
Author: Sísa, Miroslav
Pla Queral, Daniel
Altuna, Marta
Francesch, Andrés
Cuevas, Carmen
Albericio Palomera, Fernando
Álvarez Domingo, Mercedes
Keywords: Medicaments antineoplàstics
Síntesi de fàrmacs
Metabòlits marins
Antineoplastic agents
Drug synthesis
Marine metabolites
Issue Date: 18-Sep-2009
Publisher: American Chemical Society
Abstract: The first total synthesis of the indole alkaloids ()-aplicyanins A, B and E, plus seventeen analogs, all in racemic form is reported. Modifications to the parent compound included changing the number of bromine substituents on the indole, the groups 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 fourteen of the newly synthesized compounds showed considerable cytotoxicity. The assay results were used to establish structure-activity relationships. These results suggest that the acetyl group moiety on the imine nitrogen, and the bromine at position 5 of the indole, are both critical to activity.
Note: Versió postprint del document publicat a:
It is part of: Journal of Medicinal Chemistry, 2009, vol. 52, num. 20, p. 6217-6223
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ISSN: 0022-2623
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

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