Synthesis of allyl 4-O-{3-deoxy-3-[4-benzylaminocarbonyl-1H-(1,2,3)-triazol-1-yl]-β-D-galactopyranosyl}-2-deoxy-2-acetamido-β-D-glucopyranoside as a potential inhibitor of galectin-3

Abstract

Abstract: Allyl 4-O-{3-deoxy-3-[4-benzylaminocarbonyl-1H-(1,2,3)-triazol-1-yl]-β-D-galactopyranosyl}-2-deoxy-2-acetamido-β-D-glucopyranoside, a potential inhibitor of galectin-3, was designed and synthesized using lactose as staring material. The modifications of lactose included in introducing of N-acetamino group at the C-2 position through an azidoiodoglycosylation meanwhile constructing the β-aminolactoside stereoselectively and replacing 3'-OH with substituent 1,2,3-triazolyl group to enhance the affinity toward galectin-3.

Key words: Galectin-3, Galectin-3, Inhibitor, Inhibitor, Azidoiodoglycosylation, Azidoiodoglycosylation, N-acetyllactosamine derivatives, N-acetyllactosamine derivatives, ,

CLC Number:

R916.41

Supporting:

Chen Li, Xiang-Bao Meng, Xiao-Feng Jin, Zhong-Jun Li, Qing Li^*. Synthesis of allyl 4-O-{3-deoxy-3-[4-benzylaminocarbonyl-1H-(1,2,3)-triazol-1-yl]-β-D-galactopyranosyl}-2-deoxy-2-acetamido-β-D-glucopyranoside as a potential inhibitor of galectin-3[J]. .

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