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Publikācija: Synthesis of Novel 3-Deoxy-3-C-Triazolylmethyl-Allose Derivatives and Evaluation of Their Biological Activity

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Publikācijas valoda English (en)
Nosaukums oriģinālvalodā Synthesis of Novel 3-Deoxy-3-C-Triazolylmethyl-Allose Derivatives and Evaluation of Their Biological Activity
Pētniecības nozare 1. Dabaszinātnes
Pētniecības apakšnozare 1.4. Ķīmija
Autori Jekaterina Rjabova
Vitālijs Rjabovs
Antonio José Moreno Vargas
Elena Moreno Clavijo
Māris Turks
Atslēgas vārdi 3-deoxy-3-C-triazolylmethyl-allose; methylene linker; triazolyl-monosaccharides; click chemistry, inhibitors of glycosidases
Anotācija 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 latter 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 methylene linker (-CH2-) between the C(3) of allose and 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.
DOI: 10.2478/s11532-012-0002-9
Hipersaite: http://www.springerlink.com/content/x29005l152m31671/ 
Atsauce Rjabova, J., Rjabovs, V., Moreno Vargas, A., Moreno Clavijo, E., Turks, M. Synthesis of Novel 3-Deoxy-3-C-Triazolylmethyl-Allose Derivatives and Evaluation of Their Biological Activity. Central European Journal of Chemistry, 2012, Vol.10, Iss.2, 386.-394.lpp. e-ISSN 1644-3624. ISSN 1895-1066. Pieejams: doi:10.2478/s11532-012-0002-9
ID 12727