Premium
Site‐Selective Rhodium(III)‐Catalyzed C−H Amination of 7‐Azaindoles with Anthranils: Synthesis and Anticancer Evaluation
Author(s) -
Jeon Mijin,
Park Jihye,
Dey Prasanta,
Oh Yongguk,
Oh Hyunjung,
Han Sangil,
Um Sung Hee,
Kim Hyung Sik,
Mishra Neeraj Kumar,
Kim In Su
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700800
Subject(s) - chemistry , amination , rhodium , du145 , combinatorial chemistry , indole test , in vitro , aryl , stereochemistry , catalysis , biochemistry , organic chemistry , cancer cell , lncap , cancer , medicine , alkyl
The site‐selective C−H amination reaction of 7‐azaindoles with various benzisoxazoles as amination surrogates under cationic rhodium(III) catalysis is described. This transformation efficiently provides a range of ortho ‐aminated N ‐aryl‐7‐azaindoles with excellent site‐selectivity and functional group compatibility. The formed ortho ‐aminated 7‐azaindoles were readily transformed into biologically relevant heterocycles such as azaindoloacridine, azaindoloacridone, and bis‐indole compounds. Moreover, the synthetic derivatives were tested for in vitro anticancer activity against human breast adenocarcinoma cells (MCF‐7), human renal carcinoma cells (786‐O), and human prostate adenocarcinoma cells (DU145). Notably, some synthetic compounds were found to display most potent anticancer activity, compared to that of anticancer doxorubicin as a positive control.