Synthesis of novel 3-deoxy-3-C-triazolylmethyl-allose derivatives and evaluation of their biological activity |
| |
Authors: | Jekaterina Rjabova Vitālijs Rjabovs Antonio J Moreno Vargas Elena Moreno Clavijo Māris Turks |
| |
Institution: | 1.Faculty of Material Science and Applied Chemistry,Riga Technical University,Riga,Latvia;2.Institute ?BIOR”,Riga,Latvia;3.Department of Organic Chemistry, Faculty of Chemistry,University of Seville,Seville,Spain |
| |
Abstract: | Recently, monosaccharide-triazole conjugates have proved to possess a large variety of useful biological activities. This
paper describes synthesis of a new series of 3-deoxy-3-C-triazolylmethyl-allose derivatives. These new compounds are obtained from acetonide-protected 3-deoxy-3-azidomethyl allose
and commercial alkynes via Cu(I) catalyzed 1,3-dipolar cycloaddition. The obtained molecular scaffolds differ from those described
earlier by the presence of a methylene linker (-CH2-) between the C(3) of allose and the triazole moiety. It was demonstrated that acetonide-protected monosaccharide, 3-deoxy-3-C-(4-phenyl-1H-1,2,3-triazol-1-yl)methyl-1,2:5,6-di-O-isopropylidene-α-d-allofuranose, inhibited α-L-fucosidase for 26% at 0.1 mM concentration, but a deprotected analog, 3-deoxy-3-C-(4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl)methyl-β-d-allofuranose, showed 15% inhibition of β-glucosidase at 1 mM concentration.
![MediaObjects/11532_2012_2_Fig1_HTML.jpg](/content/X29005L152M31671/MediaObjects/11532_2012_2_Fig1_HTML.jpg) |
| |
Keywords: | |
本文献已被 SpringerLink 等数据库收录! |
|