Sulfated and Oxygenated Imidazoline Derivatives: Synthesis, Antioxidant Activity and Light‐Mediated Antibacterial Activity

Abstract

Imidazoline derivatives with different exocyclic substituents were simply prepared from common starting materials. The procedures were carried out in an eco‐friendly manner. The antioxidant activity of these derivatives was explored by different experimental assays, such as ABTS.+ and DPPH. scavenging assay, as well as reducing power assay. The structural differences are discussed in terms of the results. Sulfur analogs showed higher antioxidant activity than their oxygenated counterparts. The same tendency was observed in microbiological studies, in which the same imidazoline compounds were assayed for light‐mediated activity against of Staphylococcus aureus and Escherichia coli strains. A light‐enhanced activity was observed for almost all the sulfated imidazolines after exposure to UV‐A (400‐320 nm) light.

GFP-related chromophores: photoisomerization, thermal reversion, and DNA labelling

“…As described in our previous work, 5-arylmethylene thioxoimidazolidinones ( 1a–c ) were prepared through the condensation reaction of thiohydantoin with different aromatic aldehydes (path A), in 69–96% yields. 10 The 5-arylmethylene imidazothiazolone derivatives were prepared using two different synthetic approaches. The first approach for the synthesis of imidazothiazolones ( 2a–c ) was based on the reaction of ( 1a–c ) with 1,2-dichloroethane.…”

“…Synthesis of imidazolidines and imidazothiazolones (1a-c and 2a-c) were performed by microwave irradiation in a monowave 300 Anton Paar, based on previously described conventional methodologies. 10,18 Imidazolidines 1a-c were purified by column chromatography (CHCl 3 : EtOH, 90 : 10) while imidazothiazolones 2a-c were purified by preparative Thin-Layer Chromatography (CH 2 Cl 2 : EtOAc, 80 : 20). All compounds were characterized using spectroscopic techniques including NMR (1D-& 2D) and UV-vis spectroscopy as well as mass spectrometry; all acquired data are in agreement with the proposed structures.…”

“…9 Our recent findings demonstrated the antioxidant properties as well as the modulatory activity of some imidazolidinone derivatives, along with a noteworthy light-enhanced activity against S. aureus. 10,11 That is, some imidazolidinone compounds were able to inhibit the growth of S. aureus ATCC 25923 upon UV irradiation. This last result reinforces the need for understanding the photochemical features of these heterocyclic compounds from a molecular point of view.…”

Selective Synthesis using ETFBO: A New Strategy for the Preparation of Hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.

“…[28][29][30] Accordingly, we reported the antioxidant properties and microbiological activities of a family of benzylidene imidazolidines. [31,32] The reactions between ETFBO and the 2-thioxoimidazolidin-4-ones (8 a-c) were performed through MAOS (Microwave-Assisted Organic Synthesis). Initially, both reagents were mixed with triethylamine (TEA) that was added as a base.…”

“…Recently, we have been focusing on these structures due to the fact that the imidazolidine core is attributed to many biological activities being a matter of interest in medicinal chemistry [28–30] . Accordingly, we reported the antioxidant properties and microbiological activities of a family of benzylidene imidazolidines [31,32] …”