Practical Synthesis of Chalcone Derivatives and Their Biological Activities

Abstract

Practical synthesis and biological activities of 4-hydroxy-3-methoxy-2-propene derivatives are described. The novel chalcone derivatives were prepared by acid catalysed one-step condensation of 1,3- or 1,4-diacetylbenzene and 1,3,5-triacetylbenzene with 4-hydroxy-3-methoxybenzaldehyde. They were then evaluated for free radical scavenging activity, suppression of lipopolysaccharides (LPS)-induced NO generation, and anti-excitotoxicity in vitro. It was found that all compounds showed good effects for 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging, LPS-induced NO generation, and anti-neurotoxicity. Compounds 6 and 7 were potent suppressor of NO generation with the concentration range 10 µM and especially compound 8 showed very potent anti-inflammatory activity with 1 µM. In addition, the di- and tri-acetylbenzyl derivatives 6, 7, and 8 showed enhanced anti-neurotoxicity activity in cultured cortical neurons. Molecular modelling studies to investigate the chemical structural characteristics required for the enhanced biological activities interestingly revealed that compound 8 has the smallest highest occupied molecular orbital-lowest energy unoccupied molecular orbital (HOMO-LUMO) gap, which signifies easy electron and radical transfer between HOMO and LUMO in model studies.

Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors

“…The influence of electron-donor groups, like methoxyl, can be analyzed with the 2e (p-OMe), 2f (m-OMe), and 2g (p,m-OMe) analogs; the presence of these groups did not favor the activity, getting concentrations of 100, 170, and 5 × 10 4 µg/mL, respectively, in DPPH assay, having a similar behavior of the flavones 3e-g, with EC 50 of 30, 39, and 410 µg/mL. These results may appear to contrast with the reported by many authors where methoxyl groups are considered an important factor for the antioxidant activity [42,43], however, this is the case where methoxyl groups help with the lipophilicity of the molecule, for example, when the antioxidant activity is measured by the lipid peroxidation activity assay [39]. When employing DPPH test, the transfer of acid protons is required; this implies that just as in the case of the chalcones, we consider indispensable the presence of at least one hydroxyl group, explaining the lack of scavenging activity for the synthesized compounds with only methoxyl groups (3e-g).…”

Evaluation of antimicrobial, antibiofilm and carbonic anhydrase inhibition profiles of 1,3‐bis‐chalcone derivatives

“…Bis‐chalcones bearing the same characteristics as the chalcones have been drawing attention in recent years in point of synthetic applications and bioactive potentials . There are several studies in the literature on the synthesis of bis‐chalcones, the conversion to the heterocyclic compounds and the biological activities . A large majority of these studies are research on 1,4‐bis‐chalcones and studies on 1,3‐bis‐chalcones are limited.…”

Microwave-assisted synthesis of 1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one and its activities as an antioxidant, sunscreen, and antibacterial

“…Chalcone analog compounds can be synthesized by several conventional methods, such as the grinding method [11], stirring with magnetic stirrer [8], and reflux [12]. In some cases, this conventional method has several disadvantages, such as low reaction selectivity [ 13 ] and requires a relatively long reaction time [ 9 ].…”