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 stating material. The modifications of lactose included in introducing of N-acetamino group at the C-2 position through an azidoiodoglycosylation meanwhile constructing the [3-aminolactoside stereoselectively and replacing 3＇-OH with substituent 1,2,3-triazolyl group to enhance the affinity toward galeetin-3.
Adhesion of leukocytes to endothelium plays an important role in inflammation-associated diseases.Our previous studies showed that multivalent lactosides were able to inhibit this process.Using 2-azide-l,3-propandiol and glutamic acid as spacers,we synthesized divalent lactoside An-2 and tetravalent lactoside Gu-4 by means of convergent method.These two compounds displayed high anti-adhesive activity and showed therapeutic effect in rats with severe burn shock.In addition, investigation of the anti-adhesion biological mechanism using labeled compounds YAn-2 and YGu-4 demonstrated that the target of multivalent lactosides was CD11b,theβ2 integrin subunit,on the surface of leukocytes.In this paper,the synthesis of these two new multivalent lactosides as well as their fluorescein-labeled and biotin-labeled compounds is reported.
Novel prodrugs of cyclophosphamide 1a and 1b, which comprised the galactosyl moiety, the key fraction of cyclophosphamide derivates, and the linker 4-hydroxy benzaldehyde, were synthesized. These compounds were anticipated to exhibit amplified anti-tumor activity and targeting ability.
