C-cinnamoyl glycosides as a new class of anti-filarial agents

• Reaction of C-glycosylated acetone with aldehydes furnished C-Cinnamoyl glycosides.
• Borontrifluoride diethyletherate was used as catalyst for the reaction.
• Synthetic compounds were evaluated for their potential as filaricidal agents.
• Six compounds were found active in terms of MIC, IC50 and LC50 values.
• 3D QSAR analysis has been carried for active compounds.

A series of C-cinnamoyl glycosides has been synthesized in good yield by the BF3·OEt2 catalyzed aldol condensation of C-glycosylated acetone derivative with a variety of aromatic aldehydes. The synthesized compounds were evaluated for their potential as anti-filarial agents against bovine filarial parasite Setaria cervi and human filariid Wuchereria bancrofti using a number of biological assays such as relative movability (RM) assessment and MTT reduction assay. Among twenty seven test compounds six compounds were found active in terms of MIC, IC50 and LC50 values. Further biological studies were carried out using three lead compounds because of their significantly low MIC values and IC50 values compared to the standard anti-filarial drug Ivermectin. In addition, structure activity relationship study of the test compounds has been carried out using 3D-QSAR analysis.

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