Faculty of Science, Chemistry Department, Assiut University, Assiut, Egypt.
Arch Pharm (Weinheim). 2014 Feb;347(2):142-52. doi: 10.1002/ardp.201300167. Epub 2013 Dec 30.
2-Bromo-4-fluoroaniline (1) was condensed with ethyl 2-cyano-3-ethoxyacrylate (2) in ethanol to afford 3, which upon refluxing in paraffin oil at 250°C gave 8-bromo-3-cyano-6-fluoroquinoline-4(1H)-one (4). Then, compound 4 was taken as a versatile building block that allows the synthesis of thieno[3,2-c]quinoline, pyrrolo[3,2-c]quinoline, and N-methylpyrrolo[3,2-c]quinoline systems. The newly synthesized compounds and their derivatives were characterized by elemental analysis and spectroscopy (IR, (1)H NMR, (13)C NMR, and mass). Furthermore, some of these synthesized compounds were screened for their biological activities against various pathogenic bacterial and fungal strains. Our results demonstrate that most of the synthesized compounds possess a significant broad antibacterial activity against all strains of both gram-positive and gram-negative bacteria. In addition, compound 5 showed remarkable antifungal activity.
2-溴-4-氟苯胺（1）与乙基 2-氰基-3-乙氧基丙烯酸酯（2）在乙醇中缩合得到 3，将 3 在 250°C 的石蜡油中回流得到 8-溴-3-氰基-6-氟喹啉-4（1H）-酮（4）。然后，将化合物 4 用作多功能构建块，允许合成噻吩[3,2-c]喹啉、吡咯并[3,2-c]喹啉和 N-甲基吡咯并[3,2-c]喹啉系统。新合成的化合物及其衍生物通过元素分析和光谱（IR、（1）H NMR、（13）C NMR 和质谱）进行了表征。此外，对这些合成的化合物进行了筛选，以评估它们对各种致病细菌和真菌菌株的生物活性。我们的结果表明，大多数合成的化合物对革兰氏阳性和革兰氏阴性菌的所有菌株都具有显著的广谱抗菌活性。此外，化合物 5 表现出显著的抗真菌活性。
