Collect. Czech. Chem. Commun. 2004, 69, 850-866

A Linear Synthesis of 1-(β-D-Glucopyranosyl)brassinin, -brassenin A, -brassenin B and 9-(β-D-Glucopyranosyl)cyclobrassinin

Peter Kutschya,*, Marian Sabolb, Renata Maruškováa, Zuzana Čurillováa, Milan Dzurillaa, Imrich Gécia, Juraj Alföldic and Vladimír Kováčikc

a Institute of Chemical Sciences, Faculty of Science, P. J. Šafárik University, Moyzesova 11, 041 67 Košice, Slovak Republic
b Institute of Medical Biology, Medical Faculty, P. J. Šafárik University, SNP 1, 041 66 Košice, Slovak Republic
c Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, 842 38 Bratislava, Slovak Republic


The first synthesis of 1-(β-D-glucopyranosyl)brassinin, 1-(β-D-glucopyranosyl)brassenin A, 1-(β-D-glucopyranosyl)brassenin B and 9-(β-D-glucopyranosyl)cyclobrassinin, nucleoside analogs derived from indole phytoalexins, was achieved by linear approach, using the 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carbaldehyde as a starting compound. Antiproliferative and antimicrobial activity of synthesized compounds against murine leukaemia tumor cell line L1210 and selected bacteria and fungi was examined and compared with the corresponding phytoalexin aglycons.

Keywords: Indoles; Phytoalexins; Glucosides; Glycosides; Nucleosides; Nucleoside analogs; Alkaloids; Antiproliferative activity; Antimicrobial activity.

References: 48 live references.