179871-39-7Relevant academic research and scientific papers
Synthesis of Sialyl LewisX Glycomimetics Bearing a Bicyclic 3- O,4- C-Fused Galactopyranoside Scaffold
Simard, Ryan D.,Joyal, Mathieu,Gillard, Laura,Di Censo, Gianna,Maharsy, Wael,Beauregard, Janie,Colarusso, Pina,Patel, Kamala D.,Prévost, Michel,Nemer, Mona,Guindon, Yvan
, p. 7372 - 7387 (2019)
Reported herein is the synthesis of sialyl LewisX analogues bearing a trans-bicyclo[4.4.0] dioxadecane-modified 3-O,4-C-fused galactopyranoside scaffold that locks the carboxylate pharmacophore in either the axial or equatorial position. This novel series of bicyclic galactopyranosides are prepared through a stereocontrolled intramolecular cyclization reaction that has been evaluated both experimentally and by density functional theory calculations. The cyclization precursors are obtained from β-d-galactose pentaacetate in a nine-step sequence featuring a highly diastereoselective equatorial alkynylation and Cu(I) catalyzed formation of the acetylenic α-ketoester moiety. Preliminary biological evaluations indicate improved activity as P-selectin antagonists for the axially configured analogues as compared to their equatorial counterparts.
Malonate derivatives of glycolipids as cell adhesion inhibitors
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, (2008/06/13)
There is provided a novel series of malonate derivatives of glycolipid compounds of the formula STR1 wherein R is an acyl residue of a fatty acid: R1 is --(CH=CH)m --(CH2)n --CH3 ; R2, Rsu
Dicarboxymethylated glycolipid derivatives as cell adhesion inhibitors
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, (2008/06/13)
There is provided a novel series of O-carboxymethylated α- and β-glycolipid compounds of the formula STR1 wherein R is an acyl residue of a fatty acid; R1 is --(CH=CH)m --(CH2)n --CH3 ; R2,
