Antioxidant activity and docking studies of the synthesized quinazolinone derivativesa.
| Entry | Antioxidant activity | Molecular docking studies with 2HCK protein | |||||
|---|---|---|---|---|---|---|---|
| DPPH, IC50 (μg mL−1) | DMPD, IC50 (μg mL−1) | ABTS, IC50 (μg mL−1) | Docking score | H-bond interactions with AAb residues | π-cation interactions | π–π stacking interactions | |
| 1 | >300 | 280 ± 5.23 | 290 ± 3.26 | −3.865 | Arg 136 | Arg 76 | NF |
| 2 | 260 ± 3.56 | >300 | >300 | −4.047 | NF | NF | NF |
| 3 | 250 ± 2.21 | 240 ± 1.35 | 180 ± 1.65 | −4.545 | Ala 96 | NF | NF |
| 4 | 190 ± 1.40 | >300 | 240 ± 1.32 | −4.606 | Ala 96, Asn 46 | NF | NF |
| 5 | 85 ± 0.95 | 100 ± 1.56 | 70 ± 1.45 | −6.250 | Asn 46 | NF | NF |
| 6 | 50 ± 0.45 | 55 ± 0.56 | 45 ± 1.20 | −7.770 | Ala 96, Asn 46 | NF | NF |
| 7 | 35 ± 0.65 | 40 ± 0.72 | 25 ± 0.95 | −9.375 | Asp 73, Asp 73, Asn 46 | Arg 76 | NF |
| 8 | 120 ± 1.26 | 140 ± 2.36 | 150 ± 0.68 | −5.066 | Arg 76, Arg 136 | NF | NF |
| 9 | 180 ± 0.65 | 160 ± 0.65 | 145 ± 1.98 | −5.983 | Arg 136 | NF | NF |
| 10 | 70 ± 0.65 | 95 ± 1.67 | 100 ± 1.85 | −6.193 | NF | NF | NF |
| 11 | 50 ± 1.01 | 55 ± 0.98 | 45 ± 0.89 | −7.779 | Arg 136 | Arg 76 | NF |
| 12 | 25 ± 0.26 | 30 ± 0.65 | 40 ± 0.65 | −9.007 | Asp 73, Asp 73, Asn 46 | NF | Arg 136 |
| 13 | 150 ± 3.26 | 135 ± 1.69 | 160 ± 1.98 | −5.390 | Arg 136, Asn 46 | NF | NF |
| 14 | 180 ± 2.10 | 170 ± 0.98 | 155 ± 1.69 | −5.797 | Arg 136, Asn 46 | NF | NF |
| 15 | 260 ± 3.65 | >300 | 285 ± 2.65 | −3.865 | Arg 136, Gly 77 | NF | NF |
| 16 | >300 | 260 ± 3.45 | >300 | −4.188 | NF | NF | NF |
| 17 | 240 ± 2.98 | 225 ± 1.65 | 250 ± 3.56 | −4.582 | Ala 96, Asn 46, Gly 117 | NF | NF |
| 18 | >300 | 245 ± 2.56 | 280 ± 2.45 | −4.606 | Ala 96, Gly 117 | NF | NF |
| 19 | 95 ± 0.95 | 80 ± 1.20 | 75 ± 0.56 | −6.149 | Arg 136 | NF | NF |
| 20 | 45 ± 0.88 | 55 ± 0.75 | 40 ± 0.45 | −7.983 | NF | NF | NF |
| 21 | 30 ± 0.23 | 35 ± 0.98 | 35 ± 0.69 | −9.256 | Arg 136, Asp 49, Asp 49, Glu 42, Glu 42 | Arg 76 | Arg 76 |
| 22 | 150 ± 2.23 | 120 ± 2.45 | 135 ± 1.90 | −5.416 | Arg 136, Asn 46 | NF | NF |
| 23 | 200 ± 2.48 | 220 ± 1.65 | 205 ± 1.98 | −5.129 | NF | NF | NF |
| 24 | 75 ± 1.45 | 80 ± 1.70 | 100 ± 1.65 | −6.132 | Arg 136 | NF | NF |
| 25 | 35 ± 0.68 | 45 ± 1.20 | 50 ± 1.95 | −8.097 | Glu 50 | NF | NF |
| 26 | 25 ± 0.24 | 30 ± 0.50 | 45 ± 0.64 | −9.510 | Arg 136, Asp 73, Asp73, Glu 42 | Arg 76 | NF |
| 27 | 135 ± 1.98 | 150 ± 2.25 | 160 ± 1.40 | −5.309 | Asn 46, Glu 117 | NF | NF |
| 28 | 165 ± 0.65 | 140 ± 2.50 | 130 ± 2.60 | −4.973 | Arg 136 | NF | NF |
| AA | 50 ± 1.33 | 55 ± 2.26 | 45 ± 1.65 | −6.499 | Asp 73, Val 71 | NF | NF |
| GA | 60 ± 1.46 | 65 ± 1.26 | 50 ± 0.36 | −6.397 | Asp 73 | NF | NF |
a
The values are the means of three determinations, the ranges of which are <5% of the mean in all cases.
b
Amino acid; NF: not formed, AA = ascorbic acid, GA = gallic acid.