Pictet-spengler/transamination cascade reaction of indoles for modular synthesis of marinoquinoline analogues  

作　　者：Jinjin Chen Pingyu Jiang Xinping Liu Huawen Huang Guojiang Mao Guo-Jun Deng 

机构地区：[1]Key Laboratory for Green Organic Synthesis and Application of Hunan Province,Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education,College of Chemistry,Xiangtan University,Xiangtan,411105,China [2]School of Pharmaceutical Science,Hengyang Medical School,University of South China,Hengyang,421001,China [3]School of Chemistry and Chemical Engineering,Henan Normal University,Xinxiang,453007,China

出　　处：《Green Synthesis and Catalysis》2024年第4期310-314,共5页绿色合成与催化（英文）

基　　金：Support by the National Natural Science Foundation of China(Nos.22271244 and 22071211);the Hunan Provincial Natural Science Foundation of China(Nos.2023JJ40561 and 2022JJ40359);the Hunan Provincial Health Commission Foundation(B202313020111);Open Research Fund of School of Chemistry and Chemical Engineering,Henan Normal University(No.2022C02)is gratefully acknowledged.

摘　　要：The Pictet-Spengler/transamination cascade reaction enables modular synthesis of marinoquinoline analoguesthrough three-component indole ring-expansion/cyclization in the manner of novel N1–C2 cleavage of indoles.This metal-free protocol exhibits very broad functional group tolerance with up to quantitative yields. Preliminarystudies on the antitumor activity of the resultant marinoquinoline analogues reveal that the indolyl-attachedpyrrolo[2,3-c]quinoline product (5d) shows great potential (IC50 of 0.32 μg/mL to HeLa cells) as a promisinganticancer agent in clinic.

关 键 词：Pictet-spengler reaction Indole ring-expansion N1-C2 cleavage INDOLE Marinoquinoline analogues 

分 类 号：O62[理学—有机化学]