一种合成 2,3,4-三取代苯并喹啉的新方法：合成、连续反应和细胞活性†。
A New Way to 2,3,4-Trisubstituted Benzo[]quinolines: Synthesis, Consecutive Reactions and Cellular Activities †.
机构信息
Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstraße 6, 38678 Clausthal-Zellerfeld, Germany.
Department of Chemical Biology, Helmholtz Centre for Infection Research, Inhoffenstrasse 7, 38124 Braunschweig, Germany.
出版信息
Molecules. 2023 Mar 8;28(6):2479. doi: 10.3390/molecules28062479.
The reaction of mercaptoacetic acid esters with pentachloro-2-nitro-1,3-butadiene provides the appropriate precursors for the synthesis of 2,3,4-trisubstituted benzo[]quinolines. These heterocycles are easily accessible via a single-step reaction with naphthalen-1-amine or anthracen-1-amine as the precursor. Due to the steric bulk and high electron density ring, the ring closure of benzo[]quinolines takes place exclusively. Such highly substituted annelated pyridine systems can be modified in subsequent, selective reactions to build up new -heterocycles with promising microbiological properties. The antibacterial and antiproliferative assays against four mammalian cell lines demonstrate that some of the sulfur-substituted benzo[]quinoline analogs display potent phenotypic bioactivities in the single-digit micromolar range.
巯基乙酸酯与五氯-2-硝基-1,3-丁二烯的反应为合成 2,3,4-三取代苯并[]喹啉提供了合适的前体。这些杂环可以通过与萘-1-胺或蒽-1-胺作为前体的单步反应轻松获得。由于空间位阻大和电子密度高的环，苯并[]喹啉的环合仅发生。这样的高度取代的稠合吡啶系统可以在后续的选择性反应中进行修饰，以构建具有有前途的微生物学性质的新杂环。针对四种哺乳动物细胞系的抗菌和抗增殖测定表明，一些硫取代的苯并[]喹啉类似物在个位数微摩尔范围内表现出很强的表型生物活性。
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