Novel quercetin and apigenin-acetamide derivatives: design, synthesis, characterization, biological evaluation and molecular docking studies

Abstract

The interaction of new molecules obtained by the design and synthesis of flavonoid derivatives by molecular docking with DNA.

Synthesis, biological and computational studies of flavonoid acetamide derivatives

“…1 The use of lipophilic groups, such as methylene groups, between polar groups may help to reduce the polarity and improve the overall bioavailability of a molecule. 2 The antioxidant capacity of the avonoids can be explained based on electron delocalization and the formation of radicals. Taking this into perspective, a closer look at a avonol such as quercetin (1S0) shows that the antioxidant capacity will be determined by the presence of hydroxyl groups, the carbonyl group at position C-4, and the presence of double bonds in rings A, B, and C. The lone pair of electrons on the carbonyl oxygen in C-4 can trigger electron delocalization, which is facilitated by the double bonds in rings.…”

“…They possess abundant biological applications, such as anticancer and antioxidant, and can inhibit enzymes such as cyclooxygenase, prostaglandin synthase, and lipoxygenase. 1,2 The daily intake of flavonoids depends on the prevalent diet, age, culture, geographic location, and other factors. In the United States, the daily intake of flavonoids is estimated at 500–1000 mg. 3…”

“… 1 The use of lipophilic groups, such as methylene groups, between polar groups may help to reduce the polarity and improve the overall bioavailability of a molecule. 2 …”

“…The objective of this study was to synthesize flavonoid acetamide derivatives and evaluate their bioavailability, antioxidant, and ADMET properties. The flavonoid acetamide derivatives in this study are: 2,2′,2′′-((2-(3,4-bis(2-amino-2-oxoethoxy)phenyl)-4-oxo-4 H -chromene-3,5,7-triyl)tris(oxy))triacetamide (1S3); 2 2,2′-((2-(4-(2-amino-2-oxoethoxy)phenyl)-4-oxo-4 H -chromene-5,7-diyl)bis(oxy))diacetamide (2S3); 2 2,2′-((4-(3,7-bis(2-amino-2-oxoethoxy)-4-oxo-4 H -chromen-2-yl)-1,2-phenylene)bis(oxy))diacetamide (3S3); 2,2′,2′′-((2-(4-(2-amino-2-oxoethoxy)phenyl)-4-oxo-4 H -chromene-3,5,7-triyl)tris(oxy))triacetamide (4S3) and 2,2′-((4-(5,7-bis(2-amino-2-oxoethoxy)-4-oxo-4 H -chromen-2-yl)-1,2-phenylene)bis(oxy))diacetamide (5S3). The antioxidant capacity was evaluated using the DPPH· radical assay; in vitro bioavailability was determined using the dialysis tubing procedure while the ADMET properties of these compounds were determined using computational tools.…”

Evaluation of some flavanones as potential inhibitors for SARS-CoV-2 by molecular docking and pharmacological analysis

“…The grid at the ligand-binding site of the 6LU7 protein is centered at the binding site of X: -11, Y:14, Z:69, and the grid dimensions are 22 x 32 x 32 A 3 . All other software parameters were set as default, and all of the ligand's bonds were permitted to rotate freely because the receptor was assumed to be rigid (Isika et al, 2020;Şahin et al, 2022). The results of the best docking poses of the interactions were analyzed in two-and three-dimensions using Discovery Studio 2020.…”