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2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities
Tetrahedron ( IF 2.1 ) Pub Date : 2020-08-01 , DOI: 10.1016/j.tet.2020.131435
Sarah Zeghada , Ghenia Bentabed-Ababsa , Olivier Mongin , William Erb , Laurent Picot , Valérie Thiéry , Thierry Roisnel , Vincent Dorcet , Florence Mongin

By starting from a common substrate, 2-aminobenzaldehyde, both acridines and acridones were prepared. The former were generated in high yields by copper-catalyzed N-arylation followed by acid-mediated cyclization while the latter were obtained by double copper-catalyzed N-arylation followed by cyclization under the same reaction conditions. Moreover, acridine was subjected to deprotometalation by recourse to a lithium-zinc base and converted to the corresponding 4-iodo derivative, which was involved in copper-catalyzed couplings with pyrrolidinone and pyrazole. Finally, addition of pyrazole, indole and carbazole onto the 9 position of bare acridine was improved. While moderate biological activity was noticed in melanoma cells growth inhibition, the newly prepared compounds feature interesting photophysical properties which were evaluated in a preliminary study.



中文翻译:

2-氨基苯甲醛,具有生物活性的a啶和a啶的常见前体

从共同的底物2-氨基苯甲醛开始,制备了cr啶和a啶酮。前者是通过铜催化的N-芳基化反应,然后进行酸介导的环化反应而以高收率产生的,而后者是通过双重铜催化的N-芳基化,然后在相同反应条件下环化。此外,a啶通过依赖于锂锌碱进行去金属化并转化为相应的4-碘衍生物,其与吡咯烷酮和吡唑参与铜催化的偶联。最后,将吡唑,吲哚和咔唑添加到裸a啶的9位上得到改善。虽然在黑素瘤细胞生长抑制中注意到了适度的生物学活性,但新制备的化合物具有有趣的光物理性质,这些性质在初步研究中已进行了评估。

更新日期:2020-08-28
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