New ferrocene integrated amphiphilic guanidines: Synthesis, spectroscopic elucidation, DFT calculation and in vitro α-amylase and α-glucosidase inhibition combined with molecular docking approach.

Three N, N', N″-trisubstituted ferrocenyl guanidines (MG-10, MG-12 and MG-14) were synthesized, characterized by several analytical methods such as FT-IR, H and C NMR, elemental analysis and UV-visible spectroscopy. These compounds have long chain aliphatic groups therefore their aliphatic nature has been evaluated by determining their critical micelle concentration (CMC). CMC point decreases from 0.036 mM to 0.013 mM with increase in the aliphatic chain length. The quantum mechanical parameters such as the energy of frontier molecular orbitals (E and E) and the Mulliken charge distribution on the optimized structures were determined using a DFT/B3LYP method combined with the 6-31G (d,p) basis set in the gas phase. The in vitro antidiabetic activity of synthesized compounds showed that MG-12 has ICvalue 23.10 μg/mL against α-amylase while MG-10 has ICvalue 27.32 μg/mL against α-glucosidase with the respective standard Acarbose (ICvalue 20.12 μg/mL). Theoretical docking analysis demonstrated that MG-10 and MG-12 interacted with α-amylase by 3 types of interaction, including hydrogen bonds, hydrophobic interactions and electrostatic interactions.