在微波辐照下或不在微波辐照下通过点击化学合成新型氟苯基三唑及其作为 SiHa 细胞抗增殖剂的评估。

IF 1.7 4区 化学 Q3 CHEMISTRY, ORGANIC
Johana Aguilar, Elisa Leyva, Silvia Elena Loredo-Carrillo, Agobardo Cárdenas-Chaparro, Antonio Martínez-Richa, Hiram Hernández-López, Jorge Gustavo Araujo-Huitrado, Angélica Judith Granados-López, Yamilé López-Hernández, Jesús Adrián López
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引用次数: 0

摘要

目的:在微波辐照或无微波辐照的情况下,通过点击化学合成新型氟苯基三唑,并评估其在 SiHa 细胞中的抗增殖作用:背景:三唑是一种杂环化合物,含有一个由两个碳原子和三个氮原子组成的五元环。背景:三唑类化合物是含有两个碳原子和三个氮原子的五元环的杂环化合物,其中许多已被证明具有抗真菌、抗病毒、抗细菌、抗艾滋病毒、抗结核、血管扩张剂和抗癌剂等生物活性,因此非常重要:通过点击化学合成新型氟苯基三唑,并评估其抗增殖活性:方法:首先制备了几种氟苯基叠氮化物。方法:首先制备了几种氟苯基叠氮化物,在 Cu(I)催化剂存在下将这些芳基叠氮化物与苯乙炔反应,通过室温搅拌和 40ºC 微波辐照两种方法得到了相应的氟苯基三唑。此外,还评估了它们在宫颈癌 SiHa 细胞中的抗增殖活性:结果:通过微波辐照,在几分钟内就得到了氟苯基三唑。化合物 3f 在连接三唑环的碳旁边含有两个氟原子,是本研究中测试的氟苯基三唑类化合物中药效最强的。有趣的是,与不含氟原子的母体苯基三唑 3a 相比,在苯基三唑结构的特定部位添加一个氟原子会增加其抗增殖作用:在硫酸铜、抗坏血酸钠和菲罗啉存在下,通过氟苯基叠氮化物与苯乙炔反应得到了几种氟苯基三唑。用 MW 照射制备这些三唑代表了一种更好的方法,因为它们可以在几分钟内得到,而且可以得到更高产率的清洁化合物。在生物研究方面,氟原子与三唑环之间的接近性增加了其生物活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Synthesis of Novel Fluoro Phenyl Triazoles Via Click Chemistry with or without Microwave Irradiation and their Evaluation as Anti-proliferative Agents in SiHa Cells.

Aims: Perform the synthesis of novel fluoro phenyl triazoles via click chemistry with or without microwave irradiation and their evaluation as anti-proliferative agents in SiHa cells.

Background: Triazoles are heterocyclic compounds containing a five-member ring with two carbon and three nitrogen atoms. They are of great importance since many of them have shown to have biological activity as antifungal, antiviral, antibacterial, anti-HIV, anti-tuberculosis, vasodilator, and anticancer agents.

Objectives: Synthesize novel fluoro phenyl triazoles via click chemistry and evaluate their antiproliferative activity.

Methods: First, several fluorophenyl azides were prepared. Reacting these aryl azides with phenylacetylene in the presence of Cu(I) catalyst, the corresponding fluoro phenyl triazoles were obtained by two methodologies, stirring at room temperature and under microwave irradiation at 40ºC. In addition, their antiproliferative activity was evaluated in cervical cancer SiHa cells.

Results: Fluoro phenyl triazoles were obtained within minutes by means of microwave irradiation. The compound 3f, containing two fluorine atoms next to the carbon connected to the triazole ring, was the most potent among the fluoro phenyl triazoles tested in this study. Interestingly, the addition of a fluorine atom to the phenyl triazole structure in a specific site increases its antiproliferative effect as compared to parent phenyl triazole 3a without a fluorine atom.

Conclusion: Several fluoro phenyl triazoles were obtained by reacting fluoro phenyl azides with phenylacetylene in the presence of copper sulphate, sodium ascorbate and phenanthroline. Preparation of these triazoles with MW irradiation represents a better methodology since they are obtained within minutes and higher yields of cleaner compounds are obtained. In terms of biological studies, the proximity between fluorine atom and triazole ring increases its biological activity.

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来源期刊
Current organic synthesis
Current organic synthesis 化学-有机化学
CiteScore
3.40
自引率
5.60%
发文量
86
审稿时长
6-12 weeks
期刊介绍: Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.
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