Abstract An environmental friendly heterogeneous catalyst Cell-CuI-NPs was employed for the synthesis of biologically promising 1-((1-aryl)-1H-1,2,3-triazol-4-yl)methyl-5-fluoroindoline-2,3-diones via CuAAC click reaction of 5-fluoro-(1-prop-2-ynyl)indoline-2,3-dione, an alkyne with various organic azides in aqueous medium. Compounds 4b, and 4c, with MIC values 0.0075, 0.0075, 0.0082, 0.0164 μmol/mL for S. Epidermidis and B. Subtilis, respectively and compound 7b with MIC value 0.0156 for each S. Epidermidis, E. Coli, & P. Aeruginosa bacterial strains exhibited considerable antibacterial potency with the reference drug Ciprofloxacin (MIC: 0.0047 μmol/mL). On antifungal activity investigation, compound 4a, 4d, and 7c (MIC: 0.0075, 0.0082, and 0.0092 μmol/mL, respectively) for A. Niger exhibited better potency than reference drug Fluconazole (MIC: 0.0102 μmol/mL). Also, compound 4a, 4d, and 4e (MIC: 0.0075, 0.0082, and 0.0090 μmol/mL, respectively) for C. Albicans demonstrated considerable potency with respect to reference antifungal drug Fluconazole (MIC: 0.0051 μmol/mL). Antibacterial and antifungal activity results showed that incorporation of triazole unit in an alkyne 2 improved the potency. Molinspiration physicochemical parameters revealed that all the synthesized 5-fluoroisatin-triazole molecules 4a-e and 7a-e have possessed good drug like properties. Further, antimicrobial activity results were supported by the molecular docking on alkyne 2 and its active triazole 4a as well as DFT study by B3PW91 level with 6-311G(d,p) basis set. The FMOs also revealed that incorporation of triazole moiety on to alkyne 2 has improved the pharmacological activities of the resulted triazoles 4a-e and 7a-e.

中文翻译：

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5-Fluoro-1H-indole-2,3-dione-triazoles-合成、生物活性、分子对接和DFT研究

摘要 采用环境友好的多相催化剂 Cell-CuI-NPs 合成了具有生物学前景的 1-((1-aryl)-1H-1,2,3-triazol-4-yl)methyl-5-fluoroindoline-2， 3-二酮通过 5-氟-（1-丙-2-炔基）二氢吲哚-2,3-二酮（一种在水性介质中具有各种有机叠氮化物的炔烃）的 CuAAC 点击反应生成。化合物 4b 和 4c 对表皮葡萄球菌和枯草芽孢杆菌的 MIC 值分别为 0.0075、0.0075、0.0082、0.0164 μmol/mL，化合物 7b 对表皮葡萄球菌、大肠杆菌和 P. 大肠杆菌的 MIC 值分别为 0.0156细菌菌株与参考药物环丙沙星（MIC：0.0047 μmol/mL）表现出相当大的抗菌效力。在抗真菌活性研究中，化合物 4a、4d 和 7c（MIC 分别为 0.0075、0.0082 和 0.0092 μmol/mL）对 A. 尼日尔表现出比参考药物氟康唑更好的效力（MIC：0.0102 μmol/mL）。此外，化合物 4a、4d 和 4e（MIC：分别为 0.0075、0.0082 和 0.0090 μmol/mL）对白色念珠菌显示出相对于参考抗真菌药物氟康唑（MIC：0.0051 μmol/mL）相当大的效力。抗菌和抗真菌活性结果表明，在炔烃 2 中掺入三唑单元提高了效力。Molinspiration 理化参数表明，所有合成的 5-氟靛红-三唑分子 4a-e 和 7a-e 都具有良好的药物特性。此外，抗菌活性结果得到了炔烃 2 及其活性三唑 4a 的分子对接以及 B3PW91 水平的 DFT 研究和 6-311G(d,p) 基组的支持。