Abdelwahab Reham E, Elwahy Ahmed H M, Ibrahim Nada S, Abdelmoniem Amr M, Abdelhamid Ismail A
Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt.
Department of Chemistry (Biochemistry Division), Faculty of Science, Cairo University, Giza, 12613, Egypt.
BMC Chem. 2025 Mar 8;19(1):61. doi: 10.1186/s13065-025-01421-5.
A ring annelation reaction was used to successfully prepare benzo[4,5]imidazo[1,2-a][1,3,5]triazines (Systematic Name: 1,3,4a,9-tetraza-4H-fluoren-2-amines) tethered to phenoxy-N-arylacetamide, pyrazole, and 2-(4-(1-phenyl-1H-pyrazol-3-yl)phenoxy)-N-arylacetamide moieties utilizing 1-(1H-benzo[d]imidazol-2-yl)guanidine and the proper aldehydes as precursors. 2-(Phenylamino)ethyl fragment of compound 7 was cleaved off and compound 8 was formed. The constitutions of the novel compounds were confirmed based on spectral data. The antibacterial activity was evaluated for the prepared compounds against two gram-negative and two gram-positive bacteria. Among them, compound 12b (inhibition zone 16 ± 0.7 mm) was the most promising against S. aureus compared to Gentamycin (15 ± 0 mm). Also, compounds 5a and 5d exerted comparable antibacterial activity (inhibition zones 13 ± 1.4 and 13 ± 2.1 mm), respectively to Gentamycin against S. aureus. Minimum inhibitory concentration (MIC) evaluation against S. aureus showed that compound 12b had the lowest MIC value (78.1 µg/mL).
利用环化反应，以1-(1H-苯并[d]咪唑-2-基)胍和适当的醛为前体，成功制备了与苯氧基-N-芳基乙酰胺、吡唑和2-(4-(1-苯基-1H-吡唑-3-基)苯氧基)-N-芳基乙酰胺部分相连的苯并[4,5]咪唑并[1,2-a][1,3,5]三嗪（系统名称：1,3,4a,9-四氮杂-4H-芴-2-胺）。化合物7的2-(苯氨基)乙基片段被切断，形成了化合物8。基于光谱数据确认了新化合物的结构。对所制备的化合物针对两种革兰氏阴性菌和两种革兰氏阳性菌的抗菌活性进行了评估。其中，与庆大霉素（15±0mm）相比，化合物12b（抑菌圈16±0.7mm）对金黄色葡萄球菌最有前景。此外，化合物5a和5d对金黄色葡萄球菌的抗菌活性（抑菌圈分别为13±1.4和13±2.1mm）与庆大霉素相当。对金黄色葡萄球菌的最低抑菌浓度（MIC）评估表明，化合物12b的MIC值最低（78.1μg/mL）。
