New phosphinic and phosphonic acids: Synthesis, antidiabetic, anti-Alzheimer, antioxidant activity, DFT study and SARS-CoV-2 inhibition

被引:36
作者
Elkolli, Mouna [1 ]
Chafai, Nadjib [1 ]
Chafaa, Salah [1 ]
Kadi, Imededdine [2 ]
Bensouici, Chawki [3 ]
Hellal, Abdelkader [1 ]
机构
[1] Univ Ferhat ABBAS Setif, Fac Technol, Dept Proc Engn, Lab Electrochem Mol Mat Complex LEMMC, El Mabouda Campus, Setif 19000, Algeria
[2] Res Ctr Biotechnologym CRBt, Res unit Med plants URPM 3000, Constantine 25000, Algeria
[3] Ctr Rech Biotecnol, Nouvelle Ville UV 03, BP E73, Constantine, Algeria
关键词
alpha-Aminophosphinic acid; alpha-Aminophosphonic acid; One-pot three-component reaction; Anti-Alzheimer; DFT; SARS-CoV-2; ALPHA-AMINOPHOSPHONIC ACIDS; KABACHNIK-FIELDS REACTION; AZA-HENRY REACTION; BIOLOGICAL-ACTIVITY; AMINO PHOSPHONATES; HIGHLY EFFICIENT; HETEROCYCLES; DERIVATIVES; CORROSION; FACILE;
D O I
10.1016/j.molstruc.2022.133701
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Two new alpha-aminophosphinic (A) and alpha-aminophosphonic (B) acids were synthesized through a one-pot three-component reaction with good yields of 89% and 85%, respectively. The NMR and mass spectroscopies have been used to identify the obtained compounds and confirm their structures, while the IR spectroscopy has been used to characterize functional groups and the type of vibrations involved for the studied compounds. Moreover, the examination of the structural properties and the comparison between the theoretical and the experimental results have been performed using DFT/B3LYP/6-31 G (d,p) method. Consequently, the calculated values of the total energy and the energy gap indicate that the (B) is more stable and less reactive than the (A) . Also, MEP maps show that oxygen atoms are the probable sites of electrophilic reactions. In this context, the high reactivity of the (A) can be related to the replacement of the (OH) functional group by a hydrogen atom. Further, six in vitro assays have been used to evaluate the antioxidant potential of (A) and (B) , which illustrate that both compounds exhibited an excellent activity (e.g., DPPH/IC50(B): 2.42 mu g/mL and DPPH/IC50(A): 2.10 mu g /mL). The anti-Alzheimer and antidiabetic effects of the studied compounds have been estimated in vitro by evaluating their inhibition of acetylcholinesterase, butyrylcholinesterase and alpha-glucosidase. The both compounds showed a good inhibitory activity for alpha-glucosidase (IC50(A): 12.63 and IC50(B): 25.26 mu g/mL), and exhibited higher inhibitory activity against butyrylcholinesterase (BChE) than against acetylcholinesterase (AChE) (IC50(A): 36.71 & PLUSMN;0.95 and IC50(B): 26.56 & PLUSMN;1.32 mu g/mL). Furthermore, the in silico docking study of the inhibitory action of SARS-CoV-2 main protease (Mpro) showed that (A) and (B) have a significant inhibitory action with total energy values of -96.23 and -99.99 kcal/mol, respectively. (c) 2022 Elsevier B.V. All rights reserved.
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页数:13
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