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路易斯酸促进的多组分反应可生成具有抗癌活性的 2-烷基色酮。

Lewis Acid-Driven Multicomponent Reactions Enable 2-Alkyl Chromanones with Anticancer Activities.

机构信息

Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, 401331 Chongqing, China.

College of Pharmacy, National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, IATTI, Chongqing University of Arts and Sciences, Chongqing 402160, China.

出版信息

J Org Chem. 2024 Aug 16;89(16):11671-11681. doi: 10.1021/acs.joc.4c01410. Epub 2024 Aug 3.

Abstract

2-Alkyl chromanone scaffold has become prominent in pharmaceuticals and natural compounds. Consequently, devising robust strategies for synthesizing 2-alkyl chromanones remains crucial. Here, multicomponent reactions were employed to synthesize 2-alkyl chromanones containing an oxazole moiety using 3-formylchromones, amines, and -propargylamides as reactants. This method utilizes readily available feedstocks with a catalytic amount of Zn(OTf) and exhibits an impressive substrate scope compared to existing methods. Importantly, the synthesized compounds demonstrated highly selective anticancer activity against the DU145 cell line.

摘要

2-烷基色酮骨架在药物和天然化合物中已经变得突出。因此,设计合成 2-烷基色酮的稳健策略仍然至关重要。在这里,使用 3-甲酰基色酮、胺和炔丙酰胺作为反应物,通过多组分反应合成了含有噁唑基的 2-烷基色酮。该方法利用了具有催化量的 Zn(OTf)的易得原料,与现有方法相比,具有令人印象深刻的底物范围。重要的是,合成的化合物对 DU145 细胞系表现出高度选择性的抗癌活性。

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