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Synthesis, Saccharide‐Binding and Anti‐cancer Cell Proliferation Properties of Arylboronic Acid Derivatives of Indoquinolines
Author(s) -
Meng Junxiu,
Yu Shaoqing,
Wan Shengbiao,
Ren Sumei,
Jiang Tao
Publication year - 2011
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2011.01196.x
Subject(s) - chemistry , sialic acid , galactose , fucose , cell growth , aromatization , cancer cell , biochemistry , combinatorial chemistry , stereochemistry , cancer , biology , genetics , catalysis
A facile synthesis of a series of saccharide‐binding arylboronic acid derivatives of indoloquinoline was described. The key synthetic steps were polyphosphoric acid‐mediated cyclization, chlorinative aromatization, and amidation. Mass spectrometry experiments revealed these synthetic arylboronic acid derivatives of indoquinolines could bind to biologically important carbohydrates (sialic acid, fucose, glucose, and galactose) by forming boronate di‐esters in alkaline aqueous solution. Most of the arylboronic acid derivatives of indoquinolines inhibited human breast cancer cell (MDA–231) proliferation at a concentration of 5 μ m , whereas the compound 17 exhibited highest percentages (76.74%) of the cancer cell proliferation inhibition.