Glyoxyl analogs of indole phytoalexins: Synthesis and anticancer activity

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Title:Glyoxyl analogs of indole phytoalexins: Synthesis and anticancer activity
Creators:
Kutschy, Peter
Sýkora, Andrej
Čurillová, Zuzana
Repovská, Mária
Pilátová, Martina
Mojžiš, Ján
Mezencev, Roman
Pazdera, Pavel
Hromjáková, Tatiana
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 75, 8, pp. 887-903
Uncontrolled Keywords:Antiproliferative activity, Phytoalexins, Natural products, Indoles, Heterocycles, Glyoxylindoles

Abstract

Glyoxyl analogs of indole phytoalexins brassinin, 1-methoxybrassinin, brassitin, 1-methoxybrassitin and 1-methoxybrassenin B were prepared, using (1<i>H</i>-indol-3-yl)-, (1-methoxyindol-3-yl)- and [1-(2,3,4,6-tetra-<i>O</i>-acetyl-β-D-glucopyranosyl)indol-3-yl]glyoxyl chlorides as starting compounds. Synthesized products were examined for their antiproliferative activity against human cancer cell lines Jurkat (T-cell acute lymphoblastic leukemia), MCF-7 (breast adenocarcinoma, estrogen receptor-positive), MDA-MB-231 (breast adenocarcinoma, estrogen receptor-negative), HeLa (cervical adenocarcinoma), CCRF-CEM cell line (T-cell acute lymphoblastic leukemia) and A-549 cell line (lung adenocarcinoma), and their activity compared with natural phytoalexins and corresponding (1<i>H</i>-indol-3-yl)acetic acid derivatives. The highest potency with IC<sub>50</sub> 3.3–66.1 μmol l<sup>–1</sup> was found for glyoxyl analogs of 1-methoxybrassenin B.

Title:Glyoxyl analogs of indole phytoalexins: Synthesis and anticancer activity
Creators:
Kutschy, Peter
Sýkora, Andrej
Čurillová, Zuzana
Repovská, Mária
Pilátová, Martina
Mojžiš, Ján
Mezencev, Roman
Pazdera, Pavel
Hromjáková, Tatiana
Uncontrolled Keywords:Antiproliferative activity, Phytoalexins, Natural products, Indoles, Heterocycles, Glyoxylindoles
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:75
Number:8
Page Range:pp. 887-903
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc2010048UNSPECIFIED
ID Code:6197
Item Type:Article
Deposited On:11 Oct 2010 15:42
Last Modified:11 Oct 2010 13:43

Citation

Kutschy, Peter; Sýkora, Andrej; Čurillová, Zuzana; Repovská, Mária; Pilátová, Martina; Mojžiš, Ján; Mezencev, Roman; Pazdera, Pavel; Hromjáková, Tatiana (2010) Glyoxyl analogs of indole phytoalexins: Synthesis and anticancer activity. Collection of Czechoslovak Chemical Communications, 75 (8). pp. 887-903.

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