Green hemi-synthesis of novel thiazole derivatives from Ammodaucus leucotrichus Coss. & Dur. and Cuminum cyminum L. essential oils: stereochemistry, molecular fluorescence spectroscopy, in vitro biologicial activity, and molecular docking study

Abstract

This paper reports the hemi-synthesis of a new thiazole derivatives from 3-allylrhodanine under green chemical conditions (solvent free and ambient temperature). Two targeted molecules: perillaldehyde and cuminaldehyde from essential oils of Ammodaucus leucotrichus Coss. & Dur. and Cuminum cyminum L. were used. Thiazole derivatives (HRP11, 12) were obtained and characterized by FTIR, 1H NMR, 13C NMR, 2D NMR. In addition, stereochemistry of HRP11, 12 was characterized by using 2D NMR and their structural stability was confirmed by DFT calculation. Furthermore, the new products were screened for their in vitro biological activity and in silico interaction with TNF-α by using molecular docking study. A moderate antioxidant activity was found for the two obtained products evaluated by DPPH and ABTS radical scavenging techniques. Against all odds, HRP12 revealed an interesting antibacterial activity against Escherichia coli, Citrobacter freundii, and Salmonella typhimurium. Thereby, a molecular fluorescence spectroscopy was carried out to compare the fluorescence of gentamicin and that of HRP11, 12. Molecular docking performed on the Tumor Necrosis Factor (TNF-α) demonstrated sensitivity towards the thiazole derivatives obtained.