Asian Journal of Research in Chemistry
  • Year: 2015
  • Volume: 8
  • Issue: 1

Synthesis and Quantitative Structure-Antioxidant Activity Relationship Analysis of Thiazolidine-2,4-dione Analogues

1Department of Pharmaceutical Chemistry, Gokaraju Rangaraju College of Pharmacy, Hyderabad, 500090, Telangana, India

2Centre for Pharmaceutical Sciences, Jawaharlal Nehru Technological University, Hyderabad, 500072, Telangana, India

3Faculty of Technology, Osmania University, Hyderabad, 500007, Telangana, India

4Natco Research Centre, Natco Pharma Ltd, B-13, Industrial Estate, Sanath Nagar, Hyderabad, 500018, Telangana, India

*Corresponding Author E-mail: swa.pharma@gmail.com

Abstract

Three series of thiazolidine-2,4-dione analogues (1–17, 14a-h, 15a-h, 16a-h, 17a-h) were synthesized by Knoevenagel condensation/N-alkylation/combination of both the reactions. The structure of the compounds was established based on IR, 1H NMR and Mass spectral data analysis. In the in vitro antioxidant potential evaluation, the compound 14g bearing 4-hydroxyl,3-methoxyl substitution on 5-aryl functionality shown significant reducing power (IC50 22.7±0.43 μM). Descriptor-based QSAR analysis was utilized to study the structural contribution to the radical scavenging potential. Among various QSAR models, model 12 was found to be best and the R2 value 0.858 is indicative of good correlation between in vitro and in silico activity. The QSAR studies revealed the potential contribution of the descriptors HOMO, HBD, DM and SASA towards the antioxidant activity.

Keywords

Diabetes mellitus, Thiazolidine-2, 4-dione, Knoevenagel condensation, Reducing power, Molecular descriptors