Synthesis, Theoretical Study and Investigation of Biological Activity of Imidazolidine Derivatives

Abstract

In this work we synthesized imidazolidine derivatives in excellent yields using multicomponent reactions of phthalaldehyde or its derivatives, primary amines, isothiocyanate, 2,4-dihydroxyacetophenone and isopropenylacetylene in the presence of catalytic amount of Ag/KF/CP@MWCNTs NCs in water at room temperature. Also, the catalytic activity of the green synthesized Ag/KF/CP@MWCNTs NCs was evaluated in the reduction of organic pollutants such as 4-nitrophenol (4-NP) in water at mild conditions. The results indicated that the biosynthesized NCs have very high and effective catalytic activity for organic pollutants within few seconds. As well the antioxidant activity of some synthesized imidazolidine was studied using trapping of radical by DPPH and ferric reduction activity potential (FRAP) experiment. Also, the antimicrobial activity of some synthesized compounds proved by employing the disk diffusion test on Gram-positive and Gram-negative bacteria. Also, to better understanding reaction mechanism density functional theory (DFT) based quantum chemical methods have been applied. The short time of reaction, high yields of product, easy separation of catalyst and products are some benefits of this procedure.

HIGHLIGHTS

• Green chemistry is the use of a set of principles to reduce or eliminate the use or generation of unsafe materials in the design, fabrication and applications of chemical products. Among solvents, water is a green solvents and very suitable for performing organic reaction.

• The present procedure avoids the use of toxic solvent.

• Heterocyclic compounds hold a prominent position in medicinal chemistry owing to their wide spectrum of biological activities such as antimalarial, antimicrobial, antitumor, anticancer, antidepressant, antiviral, antidiabetic, anti-inflammatory and anti-HIV. Imidazolidine-2-one moiety found in variety of biologically active compounds, for example, aplysinopsin is exhibiting cytotoxicity toward cancer cells, nilutamide use for the treatment of advanced prostate cancer.

Keywords:

• Multicomponent reaction
• isothiocyanate
• isoquinoline
• five component reactions
• phthalaldehyde
• 2,4-dihydroxyacetophenone

Disclosure statement

No potential conflict of interest was reported by the author(s).