title: Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists.
abstract: A collection of iminocoumarylmethyl glycoside derivatives have been prepared by copper-catalyzed multi-component reaction of carbohydrate propargyl derivatives, sulfonyl azides, and salicylaldehyde or o-hydroxy acetophenone. The method is simple, versatile to all three components, and exceptionally high yielding. The carbohydrate N-sulfonyl iminocoumarine hybrid molecules were evaluated for binding galectin-1, -2, -3, -4N, -4C, -7, -8N, -9N, and 9C using a competitive fluorescence polarization assay. Selective compounds were identified against galectin-3, 7, 8N, and 9N with up to 40-fold affinity enhancements relative to methyl α-d-galactopyranoside due to the coumarylmethyl moieties.
authors: Centre for Analysis and Synthesis, Department of Chemistry, Lund University, POB 124, SE-221 00 Lund, Sweden; Indian Institute of Science Education and ResearchKolkata, Mohanpur, Nadia 741252, India.
authors: Vishal Kumar
authors: VK
authors: Rajput
authors: Section MIG, Department of Laboratory Medicine, Lund University, Sölvegatan 23, SE-223 62 Lund, Sweden.
authors: Hakon
authors: H
authors: Leffler
authors: Centre for Analysis and Synthesis, Department of Chemistry, Lund University, POB 124, SE-221 00 Lund, Sweden.
authors: Ulf J
authors: UJ
authors: Nilsson
authors: Indian Institute of Science Education and ResearchKolkata, Mohanpur, Nadia 741252, India. Electronic address: sugarnet73@hotmail.com.
authors: Balaram
authors: B
authors: Mukhopadhyay
mesh_terms: D003373:Coumaric Acids / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D037161:Galectins / Q000037:antagonists & inhibitors*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D003373:Coumaric Acids; D037161:Galectins; D006027:Glycosides
keywords: Antagonist; Coumarine; Galectin; Iminocoumarine; Multicomponent reaction