Erdoğan Helin, Yılmaz Özgür, Çevik Pınar Küce, Doğan Merve, Özen Recep
Department of Chemistry, Faculty of Sciences, Mersin University, 33343, Mersin, Turkey.
Department of Molecular Biology and Genetic, Faculty of Science and Arts, Harran University, 63290, Sanliurfa, Turkey.
Chem Biodivers. 2023 Sep;20(9):e202300684. doi: 10.1002/cbdv.202300684. Epub 2023 Sep 5.
In this study, Schiff bases were synthesized by utilizing the reaction of 4- and 5-aminoindane with substituted benzaldehydes. After the reduction of isolated Schiff bases with NaBH , the corresponding secondary amine derivatives were obtained. The structures of all synthesized molecules were confirmed by H-NMR, C-NMR, FT-IR, and ESI-MS. Antioxidant activities of all synthesized molecules were investigated by DPPH method, and IC values were calculated. In addition, antibacterial activities of targets were investigated by the well diffusion method, and then MIC99 values were calculated. While only four of the sixteen synthesized molecules showed a high level of antioxidant activity, all of the molecules exhibited biological activity against Gram-positive and Gram-negative bacteria to varying degrees. In addition, all the synthesized molecules showed high antifungal activity. In antioxidant capacity studies, the IC values of 2-(((2,3-dihydro-1H-inden-5-yl)amino)methyl)-6-methoxyphenol (4 d) and 2-(((2,3-dihydro-1H-inden-4-yl)amino)methyl)-6-methoxyphenol (7 d) were determined to be 18.1 μg and 35.1 μg, respectively, and these values are much stronger than BHT (butylated hydroxytoluene) and BHA (butylated hydroxyanisole) used as positive controls. The fact that targets have the same core structure with different substituents has revealed a good structure-activity relationship.
在本研究中，通过利用4-氨基茚满和5-氨基茚满与取代苯甲醛的反应合成了席夫碱。用硼氢化钠还原分离得到的席夫碱后，得到了相应的仲胺衍生物。所有合成分子的结构均通过氢核磁共振、碳核磁共振、傅里叶变换红外光谱和电喷雾电离质谱得以确证。采用二苯基苦味酰基自由基（DPPH）法研究了所有合成分子的抗氧化活性，并计算了半数抑制浓度（IC）值。此外，采用滤纸片扩散法研究了目标物的抗菌活性，然后计算了最低抑菌浓度99（MIC99）值。虽然16个合成分子中只有4个表现出高水平的抗氧化活性，但所有分子均对革兰氏阳性菌和革兰氏阴性菌表现出不同程度的生物活性。此外，所有合成分子均表现出较高的抗真菌活性。在抗氧化能力研究中，2-(((2,3-二氢-1H-茚-5-基)氨基)甲基)-6-甲氧基苯酚（4d）和2-(((2,3-二氢-1H-茚-4-基)氨基)甲基)-6-甲氧基苯酚（7d）的IC值分别测定为18.1μg和35.1μg，这些值比用作阳性对照的丁基羟基甲苯（BHT）和丁基羟基茴香醚（BHA）要强得多。目标物具有相同的核心结构但带有不同取代基这一事实揭示了良好的构效关系。
