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Synthesis of Novel Fluoro Phenyl Triazoles Via Click Chemistry with or without Microwave Irradiation and their Evaluation as Anti-proliferative Agents in SiHa Cells
Current Organic Synthesis ( IF 1.8 ) Pub Date : 2023-06-23 , DOI: 10.2174/1570179420666230420084000
Johana Aguilar 1 , Elisa Leyva 1 , Silvia Elena Loredo-Carrillo 1 , Agobardo Cárdenas-Chaparro 2 , Antonio Martínez-Richa 3 , Hiram Hernández-López 4 , Jorge Gustavo Araujo-Huitrado 5 , Angélica Judith Granados-López 5 , Yamilé López-Hernández 5 , Jesús Adrián López 5
Affiliation  

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, vas-odilator, and anticancer agents. Objectives: Synthesize novel fluoro phenyl triazoles via click chemistry and evaluate their anti-proliferative activity Methods: First, several fluorophenyl azides were prepared. Reacting these aryl azides with phe-nylacetylene in the presence of Cu(I) catalyst, the corresponding fluoro phenyl triazoles were ob-tained by two methodologies, stirring at room temperature and under microwave irradiation at 40 ºC. In addition, their antiproliferative activity was evaluated in cervical cancer SiHa cells Results: Fluoro phenyl triazoles were obtained within minutes by means of microwave irradia-tion. The compound 3f, containing two fluorine atoms next to the carbon connected to the tria-zole ring, was the most potent among the fluoro phenyl triazoles tested in this study. Interesting-ly, 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. Prepa-ration of these triazoles with MW irradiation represents a better methodology since they are ob-tained 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.

中文翻译:

通过点击化学在有或没有微波辐射的情况下合成新型氟苯基三唑及其作为 SiHa 细胞抗增殖剂的评价

目的:在有或没有微波辐射的情况下,通过点击化学合成新型氟苯基三唑,并对其作为 SiHa 细胞中的抗增殖剂进行评估。 背景:三唑是含有两个碳和三个氮原子的五元环的杂环化合物。它们非常重要,因为其中许多已显示出具有抗真菌、抗病毒、抗菌、抗艾滋病毒、抗结核、血管扩张剂和抗癌剂等生物活性。目的: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,制备几种氟苯基叠氮化物。在 Cu(I) 催化剂存在下,这些芳基叠氮化物与苯乙炔反应,通过室温搅拌和 40 ℃ 微波照射两种方法得到相应的氟苯基三唑。此外,还在宫颈癌 SiHa 细胞中评估了它们的抗增殖活性。 结果:通过微波辐射在几分钟内获得氟苯基三唑。化合物 3f 在与三唑环连接的碳旁边含有两个氟原子,是本研究测试的氟苯基三唑中最有效的。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位点添加氟原子增强了其抗增殖作用。结论:在硫酸铜、抗坏血酸钠和菲咯啉存在下,氟代苯基叠氮化物与苯乙炔反应得到了多种氟代苯基三唑。用微波辐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获得,并且可以获得更高产率的清洁化合物。在生物学研究方面,氟原子与三唑环接近,增加了其生物活性。
更新日期:2023-06-23
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