利用芳基重氮四氟硼酸盐的多用途反应性合成具有抗癌潜力的新型等铬烯-融合cf3取代吡唑

IF 2.7 4区 化学 Q1 CHEMISTRY, ORGANIC
Dr. Ana Andrijević, Milica Marković, Dr. Milica Selaković, Dr. Nađa Grozdanić, Dr. Tatjana Stanojković, Prof.Dr. Andrea M. Nikolić, Prof.Dr. Igor M. Opsenica
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引用次数: 0

摘要

吡唑,特别是其氟化衍生物,是药物化学中有价值的杂环基团。我们的研究小组最近开发了一锅两步合成吡唑啉[3,4-c]等色胺的方法,将两个特权结构结合成一个单一的杂交分子。基于这些衍生物的初步抗癌筛选结果,本文设计了下一代化合物文库,重点关注1-(三氟甲基)-3,5-二氢等色[3,4-c]吡唑支架的特定部分通过后期功能化衍生化。芳基重氮四氟硼酸盐的不同反应性被利用来实现这一目标,并产生了一个小而多样的化合物库。新系列的抗癌特性和选择的衍生物在人宫颈癌细胞株HeLa中显示出促凋亡活性。所获得的结果突出了这些结构作为进一步生物学研究的有效候选者,而流线型合成路线提供了进一步结构类似物的简便方法。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Exploiting the Versatile Reactivity of Aryldiazonium Tetrafluoroborate Salts in the Synthesis of New Isochromene-Fused CF3-Substituted Pyrazoles with Anticancer Potential

Exploiting the Versatile Reactivity of Aryldiazonium Tetrafluoroborate Salts in the Synthesis of New Isochromene-Fused CF3-Substituted Pyrazoles with Anticancer Potential

Exploiting the Versatile Reactivity of Aryldiazonium Tetrafluoroborate Salts in the Synthesis of New Isochromene-Fused CF3-Substituted Pyrazoles with Anticancer Potential

Exploiting the Versatile Reactivity of Aryldiazonium Tetrafluoroborate Salts in the Synthesis of New Isochromene-Fused CF3-Substituted Pyrazoles with Anticancer Potential

Pyrazoles, and in particular their fluorinated derivatives, are valuable heterocyclic moieties in medicinal chemistry. Our research group recently developed a one-pot, two-step synthesis of pyrazolo[3,4-c]isochromenes, combining two privileged structures into a single hybrid molecule. Based on the preliminary anticancer screening results of these derivatives, herein, we designed a next-generation compound library focused on the derivatization of a specific portion of the 1-(trifluoromethyl)-3,5-dihydroisochromeno[3,4-c]pyrazole scaffold via late-stage functionalization. The diverse reactivity of aryldiazonium tetrafluoroborate salts was leveraged to achieve this and generate a small but varied compound library. The new series was tested for their anticancer properties and selected derivatives demonstrated pro-apoptotic activity in the human cervical carcinoma cell lines HeLa. The obtained results highlight these structures as valid candidates for further biological studies, while the streamlined synthetic route offers a facile approach to further structural analogs.

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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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