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Issue 13, 2011
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The synthetic and biological studies of discorhabdins and related compounds

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Abstract

Various analogues of the marine alkaloids, discorhabdins, have been synthesized. The strategy contains spirocyclization with phenyliodine(III) bis(trifluoroacetate) (PIFA), oxidative fragmentation of the β-amino alcohols with the hypervalent iodine reagent C6F5I(OCOCF3)2, the detosylation and dehydrogenation reaction of the pyrroloiminoquinone unit in the presence of a catalytic amount of NaN3 and the bridged ether synthesis with HBrAcOH as the key reactions. All the synthesized compounds were evaluated by in vitro MTT assay for cytotoxic activity against the human colon cancer cell line HCT-116. Furthermore, the discorhabdin A oxa analogues were also evaluated against four kinds of tumor model cells, a human colon cancer cell line (WiDr), a human prostate cancer cell line (DU-145) and murine leukemia cell lines (P388 and L1210). For the identification of the target, discorhabdin A and the discorhabdin A oxa analogue were evaluated by an HCC panel assay. In the test, discorhabdins could have a novel mode of action with the tumor cells.

Graphical abstract: The synthetic and biological studies of discorhabdins and related compounds

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Supplementary files

Article information


Submitted
11 Jan 2011
Accepted
11 Apr 2011
First published
12 Apr 2011

Org. Biomol. Chem., 2011,9, 4959-4976
Article type
Paper

The synthetic and biological studies of discorhabdins and related compounds

Y. Wada, Y. Harayama, D. Kamimura, M. Yoshida, T. Shibata, K. Fujiwara, K. Morimoto, H. Fujioka and Y. Kita, Org. Biomol. Chem., 2011, 9, 4959
DOI: 10.1039/C1OB05058C

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