Reprint of "effect of carbohydrate amino group modifications on the cytotoxicity of glycosylated 2-phenyl-benzo[b]thiophenes and 2-phenyl-benzo[b]furans" [Bioorg. Med. Chem. Lett. 21 (2011) 2591-2596].

Abstract

In previous studies, we have identified a family of benzo[b]furan and benzo[b]thiophene derivatives linked to amino sugars (1-6) that are cytotoxic to a range of cancer cell lines. We describe here an exploration of the effect of structural modification of the amino group on one of the carbohydrate residues (4-amino-2,3,4,6-tetradeoxy-α-l-threo-hexopyranoside) on in vitro cytotoxicity. It has been found that maintaining at least one basic functional group around the C-4 position in the carbohydrate moiety is crucial for cytotoxicity. Furthermore, it appears that modifications around the C-4 position are limited by suitable hydrophilic/hydrophobic and/or ionic interactions, as well as steric constraints.

• Authors: Wei Shi, Todd L Lowary
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 21 Issue 17 Pg. 5107-12 (Sep 01 2011) ISSN: 1464-3405 [Electronic] England
• PMID: 21840476 (Publication Type: Journal Article)
• Copyright: Copyright © 2011. Published by Elsevier Ltd.