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含偶氮键的新型吡唑啉的合成、抗菌和抗氧化活性。

Synthesis, Antimicrobial and Antioxidant Activity of Some New Pyrazolines Containing Azo Linkages.

机构信息

Department of Chemistry, College of Education, Salahaddin University-Erbil, Kurdistan Region, Iraq.

出版信息

Curr Org Synth. 2024;21(7):903-916. doi: 10.2174/1570179420666230815124516.

DOI:10.2174/1570179420666230815124516
PMID:37581516
Abstract

BACKGROUND

Pyrazolines and azo-pyrazolines are influential groups of heterocyclic compounds with two nitrogen atoms inside the five-membered ring. They play an important role in a wide range of biological processes, such as antifungal, antioxidant, antimalarial and other antimicrobial activities.

OBJECTIVE

The main objective of this study is to synthesize some new heterocyclic compounds with antioxidant and antimicrobial activity Methods: One-pot three components and traditional synthesis of new azo-pyrazoline compounds were achieved in this work. The preparation process has been started by diazotizing 4-(6-methylbenzothiazol-2-yl) benzamine and its coupling reaction with 4-hydroxy acetophenone producing azo-acetophenone, followed by benzylation with benzyl chloride to form the starting material, azo-benzyloxy acetophenone. A series of substituted benzaldehydes were reacted with the latter compound via one pot and classical methods, forming new chalcones containing azo linkages and benzyloxy moieties, which were then converted into new target azo-pyrazoline derivatives.

RESULTS

The structures of the synthesized compounds were confirmed by spectroscopic techniques using FT-IR, H-NMR, C-NMR, and C- DEPT- 135 spectra. Finally, the synthesized compounds were screened for their antioxidant and antimicrobial activities against and .

CONCLUSION

Overall, the one-pot three-component synthesis of pyrazoline compounds generally provides advantages in terms of efficiency, simplicity, and time-consumption compared to classical synthesis methods. Hence, the study advocates the one-pot method because it eliminates the tedious process of making chalcones, which takes time, materials, and unnecessary effort. Therefore, this is the most convenient and effective approach to green chemistry.

摘要

背景

吡唑啉和偶氮吡唑啉是具有五元环内两个氮原子的重要杂环化合物。它们在多种生物过程中发挥着重要作用,如抗真菌、抗氧化、抗疟疾和其他抗菌活性。

目的

本研究的主要目的是合成具有抗氧化和抗菌活性的新型杂环化合物。

方法

一锅法和传统方法合成了新的偶氮吡唑啉化合物。该制备过程首先通过重氮化 4-(6-甲基苯并噻唑-2-基)苯甲胺及其与 4-羟基苯乙酮的偶联反应生成偶氮苯乙酮,然后用氯化苄进行苄基化形成起始原料偶氮苄氧基苯乙酮。一系列取代苯甲醛与后者通过一锅法和经典方法反应,形成含有偶氮键和苄氧基部分的新型查尔酮,然后将其转化为新的目标偶氮吡唑啉衍生物。

结果

通过使用 FT-IR、H-NMR、C-NMR 和 C-DEPT-135 光谱等光谱技术确认了合成化合物的结构。最后,对合成化合物进行了抗氧化和抗菌活性筛选,对抗 和 。

结论

总的来说,与经典合成方法相比,吡唑啉化合物的一锅法三组分合成在效率、简单性和时间消耗方面具有优势。因此,该研究提倡使用一锅法,因为它消除了制备查尔酮的繁琐过程,该过程耗时、耗材料且不必要。因此,这是最方便和有效的绿色化学方法。

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本文引用的文献

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Bioorg Chem. 2019 Apr;85:431-444. doi: 10.1016/j.bioorg.2019.01.014. Epub 2019 Jan 9.