Abstract
The current study is focused on the synthesis of two novel arylidene-based benzoxazines namely: 3-(3-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-yl)-1-(thiophen-2-yl)-2-propenone (PTP), and 3-(3-phenyl-3,4-dihydro-2H-benzo[e][1,3]-oxazin-6-yl)-1-(pyridin-2-yl)-2-propenone (PPP). The benzoxazines were obtained as condensation products of the reaction of each of the phenol analogs: [3-(4-hydroxyphenyl)-1-(2-thiophenyl)-2-propenone] (HTP), and [3-(4-hydroxyphenyl)-1-(2-pyridinyl)-2-propenone] (HPP), with aniline, and paraformaldehyde, respectively. PTP and PPP were structurally confirmed using analysis such as ultraviolet (UV) spectroscopy, together with FTIR, and H-1-NMR and C-13-NMR spectral analyses, respectively. The benzoxazine derivatives revealed an excellent antimicrobial activity against the selected bacterial (including Gram-positive & Gram-negative) and fungi. The antimicrobial activity was also investigated using the agar diffusion approach. The qualitative assay of the biological study from the inhibition zones for the PTP, PPP, and PBO revealed interesting results. The examinations revealed some levels of antimicrobial efficacy against the selected bacterial strains used. However, the biological efficacy of PTP appeared to be better with larger zones of inhibition against the growth of the micro-organisms. Moreover, the molecular docking studies of PTP, PPP, and PBO derivatives were screened against the "5FSA" protein. PPP derivative displayed a good activity than the other derivatives PTP and PBO in docking with 5FSA protein. The obtained values were -7.34, -7.70, and -5.70 Kcal/Mol for PPP, PTP, and PBO respectively compared to Fluconazole reference value -7.86 Kcal/Mol.