ABSTRACT
Polyacetylene glycosides (PAGs) constitute a relatively small class of secondary metabolites characterized by the presence of a sugar unit anomerically connected to a polyacetylene. These compounds are found in fungi, seaweed, and more often in plants. PAGs exhibit a wide range of biological and pharmacological activities and, as a result, the literature of these compounds has grown exponentially in recent years.
Subject(s)
Glycosides , Polyynes , Fungi , Plants , Polyacetylene PolymerABSTRACT
Enulosides, carbohydrate derivatives containing an α,ß-unsaturated carbonyl unit, were designed and obtained in high yields and isomeric purity. All synthesized compounds exhibited antitumoral activity in micromolar range against four tested tumor cells lines, being the best results observed for HL-60 cells. These compounds open new possibilities to prepare an array of more active, site-specific or selective antitumor agents. 2016 Elsevier Ltd. All rights reserved.
Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Biological Products/pharmacology , Carbohydrates/chemistry , Cell Proliferation/drug effects , Drug Design , Biological Products/chemistry , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Neoplasms/drug therapy , Neoplasms/pathology , Structure-Activity Relationship , Tumor Cells, CulturedABSTRACT
1,3-Dipolar cycloaddition of methylideneaniline N-oxide to sugar enones is described. The addition occurred exclusively from the side opposite to the aglycone affording the corresponding alkyl alpha-D-lyxo-hexopyranosid-(2,3:5',4')-phenylisoxazolidin-4-uloses. Hydrogenation of these compounds readily yielded the corresponding alkyl 3-deoxy-3-N-phenylaminomethyl-alpha-D-talopyranoside, that were readily transformed to the acetates. The structure and conformation of the bicyclic compounds were determined by 1H NMR studies and semi-empirical molecular orbital calculations employing the AM1 method.
