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Synthesis and Anticancer Activity of 3,4-Diaryl-1,2-dihydro- and 1,2,3,4-Tetrahydroquinolines
Molecules ( IF 4.2 ) Pub Date : 2024-09-09 , DOI: 10.3390/molecules29174273
Santosh Rajput 1 , Valerio Falasca 1 , Mohan Bhadbhade 2 , David StC Black 1 , Naresh Kumar 1
Molecules ( IF 4.2 ) Pub Date : 2024-09-09 , DOI: 10.3390/molecules29174273
Santosh Rajput 1 , Valerio Falasca 1 , Mohan Bhadbhade 2 , David StC Black 1 , Naresh Kumar 1
Affiliation
Tetrahydroquinolines are key structures in a variety of natural products with diverse pharmacological utilities and other applications. A series of 3,4-diaryl-5,7-dimethoxy-1,2,3,4-tetrahydroquinolines were synthesized in good yield by reacting 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones with different Grignard reagents followed by the dehydration of the intermediate phenolic compounds. Subsequent reduction and deprotection were carried out to achieve the desired tetrahydroquinolone moiety. The lead compound 3c showed low micromolar inhibition of various cancer cell lines. Demethylation under different reaction conditions was also investigated to afford the corresponding monohydroxy analogues.
中文翻译:
3,4-二芳基-1,2-二氢和1,2,3,4-四氢喹啉的合成及抗癌活性
四氢喹啉是具有多种药理用途和其他应用的各种天然产物的关键结构。通过3-芳基-5,7-二甲氧基-2,3-二氢喹啉-4-酮反应,以良好的收率合成了一系列3,4-二芳基-5,7-二甲氧基-1,2,3,4-四氢喹啉与不同的格氏试剂反应,然后中间体酚类化合物脱水。随后进行还原和脱保护以获得所需的四氢喹诺酮部分。先导化合物 3c 对多种癌细胞系表现出低微摩尔抑制作用。还研究了不同反应条件下的去甲基化以提供相应的单羟基类似物。
更新日期:2024-09-09
中文翻译:
3,4-二芳基-1,2-二氢和1,2,3,4-四氢喹啉的合成及抗癌活性
四氢喹啉是具有多种药理用途和其他应用的各种天然产物的关键结构。通过3-芳基-5,7-二甲氧基-2,3-二氢喹啉-4-酮反应,以良好的收率合成了一系列3,4-二芳基-5,7-二甲氧基-1,2,3,4-四氢喹啉与不同的格氏试剂反应,然后中间体酚类化合物脱水。随后进行还原和脱保护以获得所需的四氢喹诺酮部分。先导化合物 3c 对多种癌细胞系表现出低微摩尔抑制作用。还研究了不同反应条件下的去甲基化以提供相应的单羟基类似物。