Acetophenone Mannich bases: study of ionic liquid catalysed synthesis and antioxidative potential of products

Abstract

Three-component Mannich reaction of acetophenone or 4-iodoacetophenone with a variety of substituted anilines and benzaldehyde, catalysed with diethanolammonium chloroacetate, was performed under mild conditions. Mannich bases (MBs), of which five are new, were obtained in good to excellent yields. All compounds were characterized using elemental analysis, NMR and IR. In addition, detailed experimental and simulated UV–Vis spectral characterization of these compounds is presented here for the first time. In vitro antioxidative potential of synthetized MBs was evaluated using 2,2-diphenyl-1-picryl-hydrazyl radical and density functional theory (DFT) thermodynamical study. It was shown that compounds with anisidine moiety express moderate antioxidative activity. Mechanism of the organocatalysed Mannich reaction was thoroughly inspected by means of DFT. The reaction undergoes the hydrogen bonding-assisted mechanism. Moreover, the proposed rate determining step of the overall reaction is water elimination in the process of iminium ion formation. To the extent of our knowledge, this is the first detailed report on the influence of this type of catalyst on the formation of iminium ion, as a crucial intermediate for the whole reaction.

Immunotoxicity of ionic liquid [C14mim]BF4 in rats

“…5,6 In addition to the aforementioned physical and chemical feature, ILs have an infinite variety of potential anion and cation choices and exchanges, leading to qualities like hydrophobicity, viscosity, density, solubility, and biodegradability that are specified and closely regulated. 7,8 It has many uses in the creation of functional materials 9 as well as chemical synthesis, 10 biomass conversion, 11 extraction, and separation. 12 In recent years, however, a growing body of research has revealed that the "green" is not true.…”

Sustainable approach for the synthesis of chiral β-aminoketones using an encapsulated chiral Zn(ii)–salen complex

“…2 Due to their low reactivity and difficulties in restraining facial stereoselectivity, some enantioselective chiral catalytic C-C bond formation reactions with carbonyl are available, despite being effective procedures for enantioselective reduction of ketones. 3 In contrast, salen-metal complexes may be useful as bifunctional Lewis acid-base catalysts for contemporary catalytic reactions with imperative substrates. 4 Scientists have embraced Green Chemistry principles over the past few decades, and environmental considerations have become part of chemical processes.…”

Recent advances in biological applications of mannich bases — An overview

“…In medicine, mannich base and its derivatives are regarded as the best pharmacophore. [4][5][6] The phenolic mannich base, which has the structural components of a phenolic hydroxyl group and an aminoalkyl moiety, exhibits a wide range of biological activities, including anti-oxidant, anti-inflammatory, biometal chelating, anticholinesterase, and monoamino oxidase inhibitory properties. Apoptosis, cell cycle arrest, depolarization of the mitochondrial membrane and poorer topoisomerase-II inhibition were all a result of the mannich base's cytotoxicity.…”

“…According to functional group presence and activity relationships, the final analogs' antioxidant efficacies can be rated as follows: F > Cl > NO 2 > CH 3 > OCF 3 > CF 3 . Based on Gibbs free energy, an in vitro DPPH radical experiment revealed the molecule containing the anisidine moiety, 1-(4-iodophenyl)-3-((4-methoxyphenyl)amino)-3phenylpropan-1-one (55) has a superior radical scavenging activity 5,29.…”