## 3 Results and Discussion
### Antiproliferative Assay
\begin{table}
\begin{tabular}{c c c c c c c c} \hline \hline \multirow{2}{*}{**Compound**} & \multirow{2}{*}{**Substitute**} & \multicolumn{6}{c}{**Cell Lines (GI\({}_{50}\), \(\upmu\)M)**} \\ \cline{3-8}  & & **A549** & **HBL-100** & **HeLa** & **SW1573** & **T-47D** & **WiDr** \\ \hline
**1b ** & -H & \(>\)100 & \(>\)100 & \(>\)100 & 89 & \(>\)100 & \(>\)100 \\
**2** & _o_-OH & \(11\pm 5.5\) & **7.0 \(\pm\) 2.0** & **4.3 \(\pm\) 0.6** & **3.6 \(\pm\) 0.2** & \(18\pm 0.3\) & \(19\pm 0.5\) \\
**3** & _p_-OH & \(19\pm 4.0\) & \(16\pm 0.4\) & \(13\pm 2.5\) & \(15\pm 2.3\) & \(20\pm 1.5\) & \(22\pm 0.7\) \\
**4** & _p_-OMe & \(>\)100 & \(>\)100 & \(>\)100 & \(>\)100 & \(>\)100 & \(>\)100 \\
**5b ** & _m_-OMe, & \(100\pm 100\) & \(>\)100 & \(76\) & \(>\)100 & \(>\)100 \\
**6** & _o_-OHe & \(>\)100 & \(>\)100 & \(>\)100 & \(>\)100 & \(>\)100 \\
**7** & _m_-OHe, & \(17\pm 1.3\) & \(17\pm 0.7\) & \(  
The best set of synthesized molecules were **2** (_o_-OH), **10** (_p_-N(CH\({}_{3}\))\({}_{2}\)) and **11** (_p_-NO\({}_{2}\)) as they showed the overall lowest GI\({}_{50}\) values. In particular, **2** presented significant activity against lines SW1573 and HeLa with values of 3.6 and 4.3 uM; **10** showed significant activity against the majority of cell lines, where the outstanding results were against A549 with GI\({}_{50}\) of 3.8 uM, and against SW1573 with 4.4 uM. The most active compound against all of the analyzed cell lines was **11**, as its GI\({}_{50}\) was between 2.9 to 6.3 uM, with SW1573 being the most sensitive line. These two most active compounds had a substitution in their A ring in the _para_ position, where the second most active was a tertiary amine nitrogen, and the most active had a nitro group. One of the most sensitive cell lines to the synthesized compounds and the evaluated drugs was SW1573, which is from alveolar carcinoma. This is despite the line belonging to a lung cancer lineage which, as mentioned before with A549, are pharmacotherapy resistant carcinomas. However, these two lung related cell lines showed that they were sensitive to compound **11**, with GI\({}_{50}\) values of 6.3 for A549 and 2.9 uM for SW1573, which were the second lowest and the lowest values, respectively, for these lines. In 2017, Dake's research team [45] reported the synthesis and evaluation of triphenyl imidazole derivatives with substitutions in their A ring against the A549 line, where their compound 6f showed an IC\({}_{50}\) of 15 uM. This molecule has _m_-I, _m_-OMe, and _p_-OH substitutions, where the iodine is structurally similar to 7. The presence of this heteroatom improved activity by a 2 uM difference compared to not having it (17 uM for molecule **7**). The _p_-NO\({}_{2}\) substitution in compound **11** bears an important role in antiproliferative activity, which could be due to the nitroaromatic structure. Nitroaromatic compounds have gained interest as chemotherapeutic agents against cancer because molecules with nitro groups in their metabolism can go through bio-reduction, which generates reactive species that cause damage to cell components by oxidative stress; additional reductions are favored in hypoxic conditions, which generates highly cytotoxic species [46]. Even though molecule **12** is an isomer of **11**, in comparison, it showed much lower activity. This could be due to **12** having the nitro group in the _ortho_ position, where it could interact with the hydrogen in the imidazole ring, diminishing the generation of the reactive species needed for the antiproliferative activity.