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微波辅助的新型 N-芳基-二氢苯并[g]喹啉-5,10-二酮的三组分合成及其潜在的细胞毒性活性。

Microwave-Assisted Three-Component Synthesis of Novel N-Arylated-Dihydrobenzo[g]quinoline-5,10-Diones and Their Potential Cytotoxic Activity.

机构信息

Graduate University of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.

Institute of Chemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.

出版信息

Chem Biodivers. 2022 Aug;19(8):e202200359. doi: 10.1002/cbdv.202200359. Epub 2022 Aug 3.

Abstract

A convenient three-component synthetic approach was developed en route to new and significative N-arylated-dihydrobenzo[g]quinoline-5,10-diones using 2-hydroxy-1,4-naphthoquinone, a variety of aromatic aldehydes, and 4-(arylamino)furan-2(5H)-ones. A sequence of steps including Knoevenagel condensation, Michael addition, [1,3]-hydrogen shift, intramolecular cyclization and dehydration led to the formation of products. All the products were structurally characterized by spectroscopic techniques and assessed in terms of their cytotoxicity profile against four cancer cell lines (KB, HepG2, A549, and MCF7), and human embryonic kidney (Hek-293) cell lines.

摘要

一种方便的三组分合成方法被开发出来,用于通过 2-羟基-1,4-萘醌、各种芳香醛和 4-(芳氨基)呋喃-2(5H)-酮来合成新型且有意义的 N-芳基二氢苯并[g]喹啉-5,10-二酮。一系列步骤包括Knoevenagel 缩合、迈克尔加成、[1,3]-氢迁移、分子内环化和脱水,导致产物的形成。所有产物均通过光谱技术进行结构表征,并根据其对四种癌细胞系(KB、HepG2、A549 和 MCF7)和人胚肾(Hek-293)细胞系的细胞毒性特征进行评估。

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