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2-氟-N-((2-羟基苯基)亚甲基)苯甲酰肼衍生的一些过渡金属配合物的合成、表征及催化/抗菌活性

Synthesis, Characterization and Catalytic/Antimicrobial Activities of Some Transition Metal Complexes Derived from 2-Floro-N-((2-Hydroxyphenyl)Methylene)Benzohydrazide.

作者信息

Hijazi Ahmed K, Taha Ziyad A, Issa Dua'a K, Alshare Heba M, Al-Momani Waleed M, Elrashidi Ali, Barham Ahmad S

机构信息

Department of Chemistry, College of Arts and Sciences, University of Petra, P.O. Box 961343, Amman 11196, Jordan.

Department of Chemical Sciences, Faculty of Science and Arts, Jordan University of Science and Technology, P.O. Box 3030, Irbid 22110, Jordan.

出版信息

Molecules. 2024 Dec 5;29(23):5758. doi: 10.3390/molecules29235758.

Abstract

BACKGROUND

In the last few decades, the field of coordination chemistry has grown very fast, especially in the fields of pharmaceutical, biological and catalytic studies. In ancient times, metals were thought to be beneficial to health issues but nowadays the link between organic-metal substances and different industrial and medicinal properties is well established.

METHODS

A Schiff base ligand (2-fluoro-N'-[(E)-2-hydroxyphenyl) methylene] benzohydrazide) was reacted with a series of transition metals to produce complexes with a general formula [ML(NO)]NO.nHO, where [M = Zn, Cu, Co, Ni, Mn], and [n = 0, 1], corresponding to complexes -. The nature of the bond was determined in the solid state and solution using spectral studies (H-NMR, C-NMR, UV-Vis and FT-IR), TGA, EPR, elemental analysis and molar conductivity measurement.

RESULTS

All M(II) complexes are 1:1 electrolytes, as illustrated by their molar conductivities. The results demonstrate that all synthesized complexes present a coordination number of six by the bonding of the bidentate ligand via its azomethine nitrogen atoms and carbonyl oxygen atoms, as well as with one nitrate group as a bidentate ligand via two oxygen atoms. The DPPH radical scavenging technique was used to investigate the antioxidant activities of the ligand [L] and the metal complexes. It is clear that the activity increased in M (II) complexes compared to the Schiff base ligand. Complex showed the highest activity, with an excellent activity of 90.4%, while complex 4 showed the lowest. The antibacterial activities of the Schiff base and its complexes have been examined against various pathogenic bacteria to measure their inhibition potential. Complex showed remarkable activity against Gram (+) bacteria and fungi with an MIC value of 8 μg/mL, which is greater than that of the positive controls, oxytetracycline and fluconazole. The catalytic activities of all complexes were examined in the oxidation of aniline, and the results illustrated that all complexes had a 100% selectivity in producing only azobenzene, and complex had the highest activity (91%).

CONCLUSION

The obtained results from this study show that the antioxidant and antibacterial properties of both the Schiff base ligand and its derived complexes are promising, with some demonstrating remarkable activities. Moreover, the catalytic activities and selectivities of the prepared complexes in aniline oxidation are interesting.

摘要

背景

在过去几十年中,配位化学领域发展迅速,尤其是在制药、生物和催化研究领域。在古代,人们认为金属对健康有益,但如今有机金属物质与不同工业和药用特性之间的联系已得到充分确立。

方法

一种席夫碱配体(2-氟-N'-[(E)-2-羟基苯基)亚甲基]苯甲酰肼)与一系列过渡金属反应,生成通式为[ML(NO)]NO·nH₂O的配合物,其中[M = Zn、Cu、Co、Ni、Mn],[n = 0, 1],对应配合物 - 。通过光谱研究(¹H-NMR、¹³C-NMR、UV-Vis和FT-IR)、TGA、EPR、元素分析和摩尔电导率测量确定固态和溶液中的键性质。

结果

所有M(II)配合物均为1:1电解质,其摩尔电导率表明了这一点。结果表明,所有合成的配合物通过双齿配体的偶氮甲碱氮原子和羰基氧原子以及一个硝酸根作为双齿配体通过两个氧原子键合,呈现出配位数为六。采用DPPH自由基清除技术研究配体[L]和金属配合物的抗氧化活性。显然,与席夫碱配体相比,M (II)配合物的活性有所提高。配合物 表现出最高活性,优异活性为90.4%,而配合物4表现出最低活性。已检测席夫碱及其配合物对各种病原菌的抗菌活性,以测量它们的抑制潜力。配合物 对革兰氏(+)细菌和真菌表现出显著活性,MIC值为8 μg/mL,高于阳性对照土霉素和氟康唑。检测了所有配合物在苯胺氧化反应中的催化活性,结果表明所有配合物在仅生成偶氮苯方面具有100%的选择性,配合物 具有最高活性(91%)。

结论

本研究获得的结果表明,席夫碱配体及其衍生配合物的抗氧化和抗菌性能很有前景,一些表现出显著活性。此外,所制备配合物在苯胺氧化反应中的催化活性和选择性也很有趣。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/95e0/11643795/f065d702a241/molecules-29-05758-sch001.jpg

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