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Chemoselective Synthesis and Human Ecto‐5′‐nucleotidase Inhibitory Activity of 2‐Trifluoromethyl‐4,6‐diarylquinolines
Author(s) -
Rivera Rodisnel P.,
Hassan Sidra,
Ehlers Peter,
Lecka Joanna,
Sévigny Jean,
Rodríguez Eugenio T.,
Iqbal Jamshed,
Langer Peter
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800917
Subject(s) - trifluoromethyl , quinoline , chemistry , regioselectivity , aryl , ic50 , coupling reaction , stereochemistry , 5' nucleotidase , combinatorial chemistry , enzyme , in vitro , organic chemistry , biochemistry , catalysis , alkyl
Diarylated 2‐(trifluoromethyl)quinolines, containing two identical aryl groups, were prepared by Suzuki–Miyaura cross‐coupling reaction of 4,6‐dibromo‐2‐(trifluoromethyl)quinoline. In order to obtain quinolines, containing two different aryl groups, the starting material had to be modified in order to obtain a high degree of regioselectivity of the reaction. The 6‐bromo‐4‐chloro‐2‐(trifluoromethyl)quinoline with arylboronic acids allowed for a one‐pot, two‐step synthesis of various products in very good yields. The synthesized derivatives were evaluated for their potential to inhibit ecto‐ 5 ′‐nucleotidase, both human and rat source. Most derivatives exhibited selective inhibition on human ecto‐ 5 ′‐nucleotidases ( h ‐e 5 ′NT) with significant inhibitory concentration (IC 50 ) values. The results were evaluated by docking studies.