Collect. Czech. Chem. Commun.
2010, 75, 887-903
https://doi.org/10.1135/cccc2010048
Published online 2010-08-31 09:18:53
Glyoxyl analogs of indole phytoalexins: Synthesis and anticancer activity
Peter Kutschya,*, Andrej Sýkorab, Zuzana Čurillováa, Mária Repovskáa, Martina Pilátovác, Ján Mojžišc, Roman Mezencevd, Pavel Pazderae and Tatiana Hromjákováa
a P. J. Šafárik University, Faculty of Science, Institute of Chemical Sciences, Department of Organic Chemistry, Moyzesova 11, 040 01 Košice, Slovak Republic
b University of Prešov, Faculty of Health Care, Partizánska 1, 080 01 Prešov, Slovak Republic
c P. J. Šafárik University, Faculty of Medicine, Department of Pharmacology, SNP 1, 040 66 Košice, Slovak Republic
d Georgia Institute of Technology, College of Science, School of Biology, 315 Ferst Drive, Atlanta, GA 30332, USA
e Centre for Syntheses at Sustainable Conditions and Their Management, Department of Chemistry, Masaryk University, Kotlářská 2, 611 37 Brno, Czech Republic
Abstract
Glyoxyl analogs of indole phytoalexins brassinin, 1-methoxybrassinin, brassitin, 1-methoxybrassitin and 1-methoxybrassenin B were prepared, using (1H-indol-3-yl)-, (1-methoxyindol-3-yl)- and [1-(2,3,4,6-tetra-O-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 (1H-indol-3-yl)acetic acid derivatives. The highest potency with IC50 3.3–66.1 μmol l–1 was found for glyoxyl analogs of 1-methoxybrassenin B.
Keywords: Heterocycles; Indoles; Natural products; Phytoalexins; Glyoxylindoles; Antiproliferative activity.
References: 42 live references.
