*2.1. General Information*

All reagents for the synthetic methodology and solvents went through purification before being used. Melting point measurements were made on a SMP11 melting point apparatus (Stuart). Di fferent models of UV–Vis spectrophotometers were employed for the UV–Vis spectra, a Genesys 20 model was used for the antioxidant assays, a Microplate reader Multiskan ™ FC was used for the acetylcholinesterase assay (both from Thermo Scientific), and a Microplate reader model PowerWave ™ XS (from BioTek) was used for the antiproliferative assay and expressed in nanometers (nm). Fourier-transform infrared spectroscopy (FTIR) was performed on a Spectrum One (Perkin-Elmer) and a Nicolet is 5 spectrophotometer (from Thermo Scientific). Nuclear magnetic resonance (NMR) spectra were obtained on a Bruker spectrometer; model Avance DPX of 400 MHz. The chemical shifts (represented by δ) are shown using tetramethylsilane (TMS) with δ: 0.00 as the internal standard. Gas chromatography mass spectrometry (GCMS) results were obtained on a TRACE 1310

and an ISQ LT models (GC and MS, respectively) from Thermo Scientific. The purification of the synthesized molecules was realized through column chromatography, employing Sigma-Aldrich Silica Gel 60 Å (230–400 mesh). To confirm the achieved purity, compounds were verified by thin-layer chromatography (TLC) employing silica plates backed on aluminum (from Merck), revealing the plates using an UV light at 254 nm.

### *2.2. Synthesis of Triphenyl Imidazole Derivatives*

A mixture of ammonium acetate (5 Eq) and acetic acid (10 mL) were refluxed; after five minutes of constant dripping, 1 Eq of the appropriate aldehyde (**1**–**13**) was added; finally after another five minutes, 1 Eq of benzil was added. Reflux was continued until completion of the reaction (verified by Thin-layer chromatography). To stop the reaction, ammonium hydroxide was added up to a pH of 9, the formed precipitate was filtered, washed using cold water, and dried. To purify the product, column chromatography or recrystallization was employed. Confirmation of all structures were achieved by mass and NMR spectra, as discussed below:

2,4,5-triphenylimidazole **(1)**: White powder (yield 95%). C21 H16 N2. Mp = >250 ◦C. IR (KBr, cm<sup>−</sup>1) = 3037(C–H aromatic), 1599 (C–C), 1323 (C–N) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 7.97 (d, *J* = 7.6 Hz, 2H), 7.51 (d, *J* = 7.2 Hz, 4H), 7.47 (t, *J* = 7.2 Hz, 2H), 7.40–7.27 (m, 7H). 13C NMR (100 MHz, CDCl3) δ: 146.29, 132.63, 131.93, 129.04, 128.75, 128.56, 128.21, 127.92, 127.27. GC-MS ( *m*/*z*) = 296 [M]+ (97), 281 (18), 207 (63), 165 (100), 147 (20), 73 (46).

2-(4,5-diphenyl-1 *H*-imidazol-2-yl) phenol **(2)**: White powder (yield 99%). C21 H16 N2O. Mp = 210–212 ◦C. IR (KBr, cm<sup>−</sup>1) = 3205 (O–H), 1601 (C–C aromatic), 1326 (C–N) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 7.70 (dd, *J*1 = 6.4, *J*2 = 1.0 Hz, 1H), 7.54 (dd, *J*1 = 8.0, *J*2 = 1.6 Hz, 4H), 7.37 (m, 6H), 7.25 (m, 1H), 7.11 (d, *J* = 8.0 Hz, 1H), 6.86 (dd, *J*1 = 8.0, *J*2 = 1.0 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ: 157.03, 145.17, 130.90, 128.81, 128.38, 128.23, 127.88, 124.30, 119.13, 117.87, 111.81. GC-MS (*m*/*z*) = 312.3 [M]+ (100), 283.1 (8), 209.1 (4), 165.2 (65), 77.2 (15).

4-(4,5-diphenyl-1 *H*-imidazol-2-yl) phenol **(3)**: White powder (yield 94%). C21 H16 N2O. Mp = 248–250 ◦C. IR (KBr, cm<sup>−</sup>1) = 3423 (O–H), 3056 (C–H aromatic), 1609 (C–C aromatic), 1280 (C–N) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 6.80 (d, 2H), 7.85 (d, *J* = 8.0 Hz, 2H), 7.46–7.19 (m, 10H). 13C NMR (100 MHz, CDCl3) δ: 157.27, 146.25, 127.64, 126.56, 121.36, 114.98. GC-MS ( *m*/*z*) = 312 [M]+ (93), 281 (14), 207 (55), 165 (100), 73 (39).

2-(4-methoxyphenyl)-4,5-diphenyl-1 *H*-imidazole **(4)**: White powder (yield 91%). C22 H18 N2O. Mp = 230–232 ◦C. IR (KBr, cm<sup>−</sup>1) = 2958 (C–H aromatic), 1492 (C–C aromatic), 1251 (C–O), 1027 (C–N) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 7.86 (d, *J*= 8.8 Hz, 2H), 7.50 (d, *J* = 7.2 Hz, 4H), 7.32–7.23 (m, 6H), 6.94 (d, *J* = 8.8 Hz, 2H), 3.80 (s, 3H). 13C NMR (100 MHz, CDCl3) δ: 159.83, 146.56, 128.23, 127.89, 127.00, 122.70, 113.97, 55.11. GC-MS ( *m*/*z*) = 326.2 [M]+ (100), 311.2 (32), 283.1 (12), 165.2 (24), 77.1 (9).

2-(3-methoxyphenyl)-4,5-diphenyl-1 *H*-imidazole **(5)**: White powder (yield 90%). C22 H18 N2O. Mp = >250 ◦C. IR (KBr, cm<sup>−</sup>1) = 2998 (C–H aromatic), 2961 (C–H, aliphatic), 1485 (C–C aromatic), 1243 (C–O), 1201 (C-N) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 12.68 (s, 1H), 7.69 (m, 2H), 7.56 (d, *J* = 7.6 Hz, 2H), 7.51 (d, *J* = 7.2 Hz, 2H), 7.46 (t, *J* = 7.2 Hz, 2H), 7.39 (t, *J* = 7.6 Hz, 2H), 7.31 (t, *J* = 7.2 Hz, 2H), 7.23 (t, *J* = 6.8 Hz, 1H), 6.95 (d, *J* = 7.2 Hz, 1H), 3.83 (s, 3H). 13C NMR (100 MHz, CDCl3) δ: 160.02, 145.81, 137.52, 135.60, 132.10, 131.53, 130.25, 129.11, 128.95, 128.63, 128.26, 127.52, 126.96, 118.08, 114.67, 110.64, 55.67. GC-MS ( *m*/*z*) = 326 [M]+ (100), 282 (10), 207 (10), 165 (74), 89 (28), 77 (21), 44 (61).

2-(2-methoxyphenyl)-4,5-diphenyl-1 *H*-imidazole **(6)**: Pale yellow powder (yield 93%). C22 H18 N2O. Mp = 200–202 ◦C. IR (KBr, cm<sup>−</sup>1) = 1601 (C–C aromatic), 1480 (C–C aromatic), 1240 (C–O), 766 (C–H) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 10.48 (s, 1H), 8.48 (dd, 1H, *J*1 = 8 Hz, *J*2 = 1.2 Hz), 7.66–7.49 (m, 4H), 7.33–7.23 (m, 7H), 7.11 (t, *J* = 7.6 Hz, 1H), 7.00 (d, *J* = 8.4 Hz, 1H), 3.99 (s, 3H). 13C NMR (100 MHz, CDCl3) δ: 155.65, 143.98, 129.46, 128.54, 127.72, 121.58, 118.05, 111.12, 55.80. GC-MS ( *m*/*z*) = 326.3 [M]+ (100), 308.2 (80), 295.1 (39), 221.2 (39), 165.2 (57), 77.2 (16).

4-(4,5-diphenyl-1*H*-imidazol-2-yl)-2-methoxyphenol **(7)**: White powder (yield 92%). C22H18N2O2. Mp = 246–248 ◦C. IR (KBr, cm<sup>−</sup>1) = 3510 (O–H), 2996 (C–H), 1601 (C–C aromatic), 1496 (C–C aromatic), 1274 (C–O), 695 (C–H) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 7.57 (d, *J* = 1.6 Hz, 1H), 7.49 (d, *J* = 6.8 Hz, 4H), 7.36–7.23 (m, 7H), 6.88 (d, *J* = 8.4 Hz, 1H), 3.88 (s, 3H). 13C NMR (100 MHz, CDCl3) δ: 147.23, 146.75, 146.63, 132.47, 128.26, 127.91, 127.11, 121.78, 118.60, 114.76, 109.08, 55.71. GC-MS (*m*/*z*) = 342 [M]+ (4), 341 (15), 311 (14), 295 (5), 165 (30), 105 (100), 77 (56), 44 (29).

2-(3,4-dimethoxyphenyl)-4,5-diphenyl-1*H*-imidazole **(8)**: White powder (yield 84%). C23H20N2O2. Mp = 220–222 ◦C. IR (KBr, cm<sup>−</sup>1) = 2959 (C–H), 1591 (C–C aromatic), 1495 (C–C aromatic), 1253 (C–O), 762 (C–H) cm<sup>−</sup>1.1H NMR (400 MHz, CDCl3) δ: 7.60 (s, 1H), 7.49 (m, 5H), 7.32 (m, 6H), 6.88 (d, *J* = 8.4 Hz, 1H), 3.89 (s, 3H), 3.86 (s, 3H). 13C NMR (100 MHz, CDCl3) δ: 149.28, 148.90, 146.51, 132.66, 128.23, 127.90, 127.05, 122.95, 118.12, 111.00, 109.04, 55.68. GC-MS (*m*/*z*) = 356 [M]+ (1), 342 (1), 281 (3), 207 (16), 193 (12), 176 (100), 165 (14), 69 (65).

2-(2-chlorophenyl)-4,5-diphenyl-1*H*-imidazole **(9)**: Pale yellow powder (yield 93%). C21H15ClN2. Mp = 190–192 ◦C. IR (KBr, cm<sup>−</sup>1) = 2924 (C–H), 1602 (C–C aromatic), 1479 (C–C aromatic), 763 (C–H), 696 (C–Cl) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 10.25 (s, 1H), 8.44 (dd, 1H, *J*1 = 7.6 Hz, *J*2 = 1.2 Hz), 7.66 (m, 2H), 7.47–7.25 (m, 11H). 13C NMR (100 MHz, CDCl3) δ: 143.20, 137.91, 134.57, 130.88, 130.48, 129.59, 129.57, 129.04, 129.02, 128.36, 128.06, 127.96, 127.79, 127.67, 127.52, 127.09. GC-MS (*m*/*z*) = 330 [M]+ (18), 281 (18), 207 (65), 176 (71), 165 (61), 89 (35), 44 (100).

4-(4,5-diphenyl-1*H*-imidazol-2-yl)-N,N-dimethylaniline **(10)**: Brown yellow powder (yield 83%). C23H21N3. Mp=234–236 ◦C. IR (KBr, cm<sup>−</sup>1)=<sup>3000</sup> (C–H), 1618 (C–C aromatic), 1497 (C–C aromatic), 1200 (C–N), 765 (C–H), 696 (C–Cl) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 9.70 (s, 1H), 7.77 (d, *J* = 8.8 Hz, 2H), 7.51 (d, *J* = 7.2 Hz, 4H), 7.30–7.21 (m, 6H), 6.70 (d, *J* = 8.8 Hz, 2H), 2.96 (s, 6H). 13C NMR (100 MHz, CDCl3) δ: 150.74, 147.01, 132.98, 129.94, 129.06, 128.48, 127.85, 127.15, 126.56, 112.14, 40.32. GC-MS (*m*/*z*) = 339 [M]+ (6), 325 (4), 313 (17), 269 (23), 178 (53), 165 (100), 89 (42), 77 (38).

2-(4-nitrophenyl)-4,5-diphenyl-1*H*-imidazole **(11)**: Yellow powder (yield 90%). C21H15N3O2. Mp = 230–232 ◦C. IR (KBr, cm<sup>−</sup>1) = 2923 (C–H), 1600 (C–C aromatic), 1519 (N–O), 1486 (C–C aromatic), 1339 (N–O), 765 (C–H) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 8.19 (d, *J* = 8.8 Hz, 2H), 8.06 (d, *J* = 8.8 Hz, 2H), 7.53–7.45 (m, 4H), 7.33 (m, 6H). 13C NMR (100 MHz, CDCl3) δ: 147.03, 143.89, 135.83, 128.53, 128.04, 125.70, 124.14. GC-MS (*m*/*z*) = 341 [M]+ (1), 330 (10), 281 (4), 220 (10), 176 (100), 165 (24), 89 (21), 69 (60), 45 (40).

2-(2-nitrophenyl)-4,5-diphenyl-1*H*-imidazole **(12)**: Red powder (yield 77%). C21H15N3O2. Mp = 210–212 ◦C. IR (ATR diamond, cm<sup>−</sup>1) = 2926 (C–H), 1598 (C–C aromatic), 1517 (N–O), 1485 (C–C aromatic), 1331 (N–O), 759 (C–H) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 8.34 (d, *J* = 8.0 Hz, 2H), 8.11 (d, *J* = 8.0 Hz, 2H), 7.69–7.30 (m, 10 H). 13C NMR (100 MHz, CDCl3) δ: 147.44, 143.40, 139.83, 135.48, 133.99, 130.27, 129.39, 129.10, 128.57, 128.47, 127.97, 127.71, 127.47, 125.46, 124.43. GC-MS (*m*/*z*) = 341 [M]+ (48), 311 (10), 237 (5), 165 (28), 135 (31), 104 (100), 89 (60), 79 (29).

2-(anthracen-9-yl)-4,5-diphenyl-1*H*-imidazole **(13)**: Pale yellow powder (yield 64%). C29H20N2. Mp = 204–206 ◦C. IR (ATR diamond, cm<sup>−</sup>1) = 3074–3020 (C–H), 1609 (C–C aromatic), 1447 (C–C aromatic) cm<sup>−</sup>1. 1H NMR (400 MHz, CDCl3) δ: 8.47 (s, 1H), 8.00 (d, *J* = 8.0 Hz, 2H), 7.92 (d, *J* = 8.0 Hz, 2H), 7.64–7.27 (m, 14H). 13C NMR (100 MHz, CDCl3) δ: 143.60, 131.49, 131.10, 128.91, 128.61, 128.42, 127.83, 127.40, 126.55, 125.83, 125.31, 124.58. GC-MS (*m*/*z*) = 396.2 [M]+ (100), 323.1 (3), 291.1 (4), 203 (10), 165 (16), 105 (8), 77 (4).

### *2.3. In Vitro Antioxidant Activity Assay*

### 2.3.1. 1,1-Diphenyl-2-Picrylhydrazyl (DPPH) Radical-Scavenging Assay

For the determination of the radical-scavenging activity, we used our implementation of the Salazar-Aranda et al. [16] method. A set of serial dilutions in methanol were prepared for each sample. Then, 0.5 mL aliquots of each dilution were mixed with a solution of 1,1-diphenyl-2-picrylhydrazyl (DPPH) in methanol (0.5 mL, 76 μM). The resulting mixtures were kept in the dark at room temperature

for 30 min. The absorbance of each sample was measured at 517 nm ( *A*517) and methanol was used as the blank. To calculate the radical-scavenging activity as DPPH decoloration percentage, the formula below was used:

$$\text{DPPH} \text{ (\%)} = [1 - \text{(B/A)}] \times 100$$

where A represents the absorbance value of the DPPH solution (used as control) and B is the absorbance of the DPPH solution with the sample. Results were expressed as EC50, which represents the required concentration to diminish the absorbance of DPPH by 50%. Quercetin was employed as the reference compound.
