A Convenient Synthesis of Glutarates Derivatives: Application, Theoretical DFT Calculations and Molecular Docking Study

Background:

An easy and convenient access to a novel Gluatarate Derivatives (DCG) was successfully synthesized, using an unusual successive S_N2-S_N2 reaction of 1,4-Diazabicyclo [2.2.2] Octane (DABCO) then KCN, on the available vinyl bromide. Fukui functions, molecular electrostatic potential and HOMO-LUMO energy of the component Gluatarate Derivatives (DCG) 2b and 3b were computed using Density Functional Theory (B3LYP/6-311+G(d,p)). The technique of molecular docking was studied to predict the interaction modes between the DCG ligand selected and with different proteins.

Materials and Methods:

The objective of our experiments was to characterize the components of DCG by NMR Spectroscopy (¹H, ¹³C, DEPT135 and HMBC) and by HRMS. Results: We developed a new approache to gluatarate derivatives involving firstly a successive S_N2-S_N2 reaction of 1,4-diazabicyclo[2.2.2]octane (DABCO) then KCN on the functional vinyl bromide. All compounds were correlated using computational DFT. The molecular docking studies revealed that glutarates derivatives 2b and 3b were as antibacterial and anti-Alzheimer activities.

Conclusion:

A new family of glutarates derivatives 2b and 3b has been described from vinyl bromide.