Synthesis and structural confirmation on selective N-alkylation of (Z)-5-((5-chloro-1H-indol-3-l)methylene)thiazolidine-2,4-dione analogues with their molecular docking studies

Abstract

In the present investigation, a series of novel (Z)-5-((5-chloro-1H-indol-3-yl)methylene)thiazolidine-2,4-dione analogues have been designed and synthesized in good yields with the objective of selective N-alkylation at thiazolidine 2,4-dione ring in competence with indole ring under basic conditions in the presence of aprotic solvent dimethylformamide (DMF). The newly synthesized compounds have been characterized by spectral data (IR, ¹H and ¹³C NMR, NOE, NOESY, ¹H-¹H-COSY and LC-MS). Further, molecular docking and ADME studies have revealed that the newly synthesized compounds have very good docking score against antidiabetic and anti-inflammation activities (PPARy and COX-2) as compared with standard rosiglitazone.