A small series of C-cinnamoyl glycosides incorporating the phenol moiety has been prepared by reaction of glycosyl ketones with the appropriate benzaldehydes. Glycosides were tested for the inhibition of twelve mammalian isoforms of carbonic anhydrase. This is the first study in which α-CAs have been investigated for their interaction with C-glycosides, a novel carbohydrate scaffold in the design of carbonic anhydrase inhibitors. The C-cinnamoyl glycosides were generally effective CA inhibitors, with inhibition constants in the low micromolar range against CA I, II, IV, VA, VB, VI, VII, IX, XII, XIII, XIV and ineffective inhibitors of CA III. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves its inhibitory activity.
Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases / L. E. Riafrecha;O. M. Rodríguez;D. Vullo;C. T. Supuran;P. A. Colinas. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - STAMPA. - 21:(2013), pp. 1489-1494. [10.1016/j.bmc.2012.09.002]
Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases.
VULLO, DANIELA;SUPURAN, CLAUDIU TRANDAFIR;
2013
Abstract
A small series of C-cinnamoyl glycosides incorporating the phenol moiety has been prepared by reaction of glycosyl ketones with the appropriate benzaldehydes. Glycosides were tested for the inhibition of twelve mammalian isoforms of carbonic anhydrase. This is the first study in which α-CAs have been investigated for their interaction with C-glycosides, a novel carbohydrate scaffold in the design of carbonic anhydrase inhibitors. The C-cinnamoyl glycosides were generally effective CA inhibitors, with inhibition constants in the low micromolar range against CA I, II, IV, VA, VB, VI, VII, IX, XII, XIII, XIV and ineffective inhibitors of CA III. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves its inhibitory activity.I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.