Synthesis and antiproliferative activity of 1-methoxy-, 1-(α-D-ribofuranosyl)- and 1-(β-D-ribofuranosyl)brassenin B

Abstract

Syntheses of indole phytoalexin 1-methoxybrassenin B and a linear synthesis of its nucleoside analogs 1-(α-D-ribofuranosyl)brassenin B and 1-(β-D-ribofuranosyl)brassenin B are reported from the corresponding 1-substituted indole-3-carboxaldehydes and carboxylic acids as key intermediates. Examination of the antiproliferative activity of synthesized compounds on human tumor cell lines Jurkat, CEM, CEM-VCR, MCF-7 and HeLa revealed the highest activity for 1-methoxybrassenin B, whereas activity of the nucleoside analogs decreased and appeared to be dependent on lipophilicity. ©ARKAT USA, Inc.