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

Priya Roy; Debashis Dhara; Pravat Kumar Parida; Rajiv Kumar Kar; Anirban Bhunia; Kuladip Jana; Santi P Sinha Babu; Anup Kumar Misra

doi:10.1016/j.ejmech.2016.03.001

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

Eur J Med Chem. 2016 May 23:114:308-17. doi: 10.1016/j.ejmech.2016.03.001. Epub 2016 Mar 7.

Authors

Priya Roy¹, Debashis Dhara², Pravat Kumar Parida², Rajiv Kumar Kar³, Anirban Bhunia³, Kuladip Jana⁴, Santi P Sinha Babu⁵, Anup Kumar Misra⁶

Affiliations

¹ Parasitology Laboratory, Department of Zoology (Centre for Advanced Studies), Visva-Bharati University, Santiniketan 731235, West Bengal, India.
² Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata 700054, India.
³ Bose Institute, Department of Biophysics, P-1/12, C.I.T. Scheme VII-M, Kolkata 700054, India.
⁴ Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata 700054, India. Electronic address: kuladip@jcbose.ac.in.
⁵ Parasitology Laboratory, Department of Zoology (Centre for Advanced Studies), Visva-Bharati University, Santiniketan 731235, West Bengal, India. Electronic address: spsinhababu@gmail.com.
⁶ Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata 700054, India. Electronic address: akmisra69@gmail.com.

PMID: 27015610
DOI: 10.1016/j.ejmech.2016.03.001

Abstract

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.

Keywords: Aldol reaction; Anti-filarial; C-glycosides; MTT reduction assay; QSAR; Setaria cervi; Wuchereria bancrofti.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cattle
Dose-Response Relationship, Drug
Filariasis / drug therapy*
Filarioidea / drug effects*
Glycosides / chemical synthesis
Glycosides / chemistry
Glycosides / pharmacology*
Humans
Molecular Structure
Quantitative Structure-Activity Relationship

Substances

Glycosides