Diacylphloroglucinol derivatives as antioxidant agents: green synthesis, optimisation, in vitro , and in silico evaluation.

Autor: Prasetyo WE; Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Surakarta, Indonesia., Kusumaningsih T; Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Surakarta, Indonesia., Firdaus M; Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Surakarta, Indonesia., Marliana SD; Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Surakarta, Indonesia., Suryanti V; Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Surakarta, Indonesia., Artanti AN; Department of Pharmacy, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Surakarta, Indonesia., Apriana I; Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Surakarta, Indonesia., Anggraini SD; Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Surakarta, Indonesia.
Jazyk: angličtina
Zdroj: Natural product research [Nat Prod Res] 2022 Mar; Vol. 36 (6), pp. 1460-1466. Date of Electronic Publication: 2021 Feb 28.
DOI: 10.1080/14786419.2021.1889542
Abstrakt: Several derivatives of diacylphloroglucinol ( 3a-3c and 5a-5b ) as an analogue of natural product compound 2,4-diacetylphloroglucinol 3a , were successfully synthesised in an excellent yield via a greener Friedel-Craft acylation using methanesulfonic acid (MSA) as a catalyst under an ultrasound-assisted condition. Operational simplicity, excellent yield, expedient metal-free synthesis, energy-efficient and mild reaction conditions are the outstanding advantages in this procedure. A scaled-up reaction also revealed the practical suitability of this newly developed procedure. The effects of several process variables on 3a were carefully accomplished using response surface methodology (RSM). Moreover, the green credentials of the present protocol have been assessed using several established green metrics and compared to relevant procedures. Along with the monomers, dimeric diacylphloroglucinols ( 6a-6e ) were also synthesised and their in vitro antioxidant activity of these species were carried out. Furthermore, drug-likeness, density functional theory (DFT), and molecular docking studies were also established.
Databáze: MEDLINE