Synthesis, antiamoebic and molecular docking studies of furan-thiazolidinone hybrids

  • Eur J Med Chem. 2016 Nov 29:124:393-406. doi: 10.1016/j.ejmech.2016.08.053.
Mohammad Fawad Ansari  1 ,  Shadab Miyan Siddiqui  1 ,  Kamal Ahmad  2 ,  Fernando Avecilla  3 ,  Sudhaker Dharavath  4 ,  Samudrala Gourinath  4 ,  Amir Azam  5
Affiliations
  • 1. Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, 110 025, New Delhi, India.
  • 2. Centre for Interdisciplinary Research in Basic Science, Jamia Nagar, 110 025, New Delhi, India.
  • 3. Departamento de Química Fundamental, Universidade da Coruña, Campus da Zapateira, 15071, A Coruña, Spain.
  • 4. School of Life Sciences, Jawaharlal Nehru University, New Delhi, 110067, India.
  • 5. Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, 110 025, New Delhi, India. Electronic address: [email protected].
PMID: 27597415 DOI: 10.1016/j.ejmech.2016.08.053
Abstract

In continuation of our previous work, a series of furan-thiazolidinone hybrids was prepared by Knoevenagel condensation of 3-(furan-2-ylmethyl)-2-(phenylimino)-1, 3-thiazolidin-4-one with different aryl aldehydes in presence of strong base. Some members of the series exhibited remarkable antiamoebic activity and cell viability. Three compounds (3, 6 and 11) showed excellent binding energy for Entamoeba histolytica O-acetyle-l-serine sulfohydrolase and Entamoeba histolytica thioredoxin reductase. These compounds demonstrated significant inhibition of O-acetyle-l-serine sulfohydrolase. The promising antiamoebic activity and enzymatic assay of 3, 6 and 11 make them promising molecules for further lead optimization in the development of novel antiamoebic agents.

Keywords
Antiamoebic activity; Furan; MTT assay; Thiazolidinone; Thioredoxin reductase.