Synthesis, characterization and molecular modeling approach of hybrid pyrazole based thiazolidinone derivatives: An estimation and inhibition of diabetes mellitus

Diabetes Mellitus (DM), a persistent metabolic disorder was the focus of study in current research work. A novel series of pyrazole based thiazolidinone derivatives (1–15) was designed and efficiently synthesized for the treatment of DM. All the novel synthesized compounds were investigated for their biological inhibitory potential against alpha-amylase and alpha-glucosidase in comparison to standard drug acarbose (IC 50 = 7.20 ± 0.10 µM and 8.10 ± 0.20 µM ). Analogue 8 (IC 50 = 6.20 ± 0.20 and 6.80 ± 0.40 µM ) demonstrated spellbinding inhibition potential surpassing the potency of standard drug. This remarkable potency of the compound 8 is due to the presence of trifluoromethyl moiety, which interacts with amino acids on receptor proteins via strong hydrogen bond. All these interactions were also visualized under in-silico molecular docking study, which revealed the insight into the binding interaction of potent compounds against target enzyme complex. Additionally, to assess drug-likeness and other pharmacokinetic properties of the potent compounds, ADME analysis was also conducted. Moreover, all the synthesized compounds were structurally analyzed via spectral studies comprising of 1 H NMR, 13 C NMR and HREI-MS.