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<p>Novel trifluoromethyl benzamides (2a-2f) were designed, synthesized, and their in vitro antibacterial and in silico anticancer abilities were tested in this investigation. This study includes many new drugs containing CF<sub>3</sub>, which is a trend because the FDA approves some new drugs with CF<sub>3</sub> and releases them into the market every year. The process began with the reaction of anthranilic acid and 2-(trifluoromethyl) benzoyl chloride, followed by reaction with acetic anhydride as a catalyst to close the ring and form benzoxazin-4-one. Ring openings were synthesized by reacting benzoxazine-4-one with aromatic amines such as aniline, <i>p</i>-toluidine, <i>m</i>-toluidine, <i>o</i>-anisidine, <i>p</i>-phenetidine, and <i>o</i>-phenetidine. Spectroscopic techniques, including <sup>13</sup>C-NMR, <sup>1</sup>H-NMR, <sup>19</sup>F-NMR, FT-IR, and UV–Vis absorption, were employed. <i>In vitro</i> antibacterial activity was screened using the well diffusion method against microorganisms (<i>E. coli</i>) as Gram-negative and (<i>S. aureus</i>) as Gram-positive. The results show that the compounds are more effective against <i>E. coli</i>. Compound (2.2.1) exhibited the highest inhibition zone (34 mm at 800 ppm), compound (2c) showed moderate activity (24 mm at 600 ppm), and compound (2b) demonstrated the lowest activity (11 mm at 800 ppm). Compounds exhibited no activity against S. aureus, with only one compound (2.2.1) showing slight activity (18 mm at 1000 ppm). <i>In silico</i> anticancer activity was tested through molecular docking at the active site of the protein, comparing the synthesized compounds with the reference (CF<sub>3</sub>). The results indicate that the ring openings of benzoxazinone have stronger activity than the reference (CF<sub>3</sub>), which shows lower S (score) (-5.64225) from Drug Bank. Compound (2d) demonstrates the highest S (score) (-6.58417) with the active site of the protein (2GH6). <i>In silico</i> antibacterial activity has been tested via MOE. The trade drug (Linezolid) was used as a ligand to compare with Novel compounds. The result shows that the compound 2d has a higher S score ( -8.12188) than the ligand and other compounds.</p> Graphical Abstract <p></p>

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Design, Synthesis, Biological Evaluation, Spectroscopic Techniques, and Computational Study of Some New Trifluoromethyl (benzamido) Benzamides

  • 期刊论文

  • 发表日期：

    2026年6月30日

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  • Zhila Abdulkareem Farhan,
  • Mzgin Mohammed Ayoob

摘要

Novel trifluoromethyl benzamides (2a-2f) were designed, synthesized, and their in vitro antibacterial and in silico anticancer abilities were tested in this investigation. This study includes many new drugs containing CF3, which is a trend because the FDA approves some new drugs with CF3 and releases them into the market every year. The process began with the reaction of anthranilic acid and 2-(trifluoromethyl) benzoyl chloride, followed by reaction with acetic anhydride as a catalyst to close the ring and form benzoxazin-4-one. Ring openings were synthesized by reacting benzoxazine-4-one with aromatic amines such as aniline, p-toluidine, m-toluidine, o-anisidine, p-phenetidine, and o-phenetidine. Spectroscopic techniques, including 13C-NMR, 1H-NMR, 19F-NMR, FT-IR, and UV–Vis absorption, were employed. In vitro antibacterial activity was screened using the well diffusion method against microorganisms (E. coli) as Gram-negative and (S. aureus) as Gram-positive. The results show that the compounds are more effective against E. coli. Compound (2.2.1) exhibited the highest inhibition zone (34 mm at 800 ppm), compound (2c) showed moderate activity (24 mm at 600 ppm), and compound (2b) demonstrated the lowest activity (11 mm at 800 ppm). Compounds exhibited no activity against S. aureus, with only one compound (2.2.1) showing slight activity (18 mm at 1000 ppm). In silico anticancer activity was tested through molecular docking at the active site of the protein, comparing the synthesized compounds with the reference (CF3). The results indicate that the ring openings of benzoxazinone have stronger activity than the reference (CF3), which shows lower S (score) (-5.64225) from Drug Bank. Compound (2d) demonstrates the highest S (score) (-6.58417) with the active site of the protein (2GH6). In silico antibacterial activity has been tested via MOE. The trade drug (Linezolid) was used as a ligand to compare with Novel compounds. The result shows that the compound 2d has a higher S score ( -8.12188) than the ligand and other compounds.

Graphical Abstract