Premium
N ‐[2‐Methyl‐5‐(triazol‐1‐yl)phenyl]pyrimidin‐2‐amine as a Scaffold for the Synthesis of Inhibitors of Bcr‐Abl
Author(s) -
Arioli Federica,
Borrelli Stella,
Colombo Francesco,
Falchi Federico,
Filippi Irene,
Crespan Emmanuele,
Naldini Antonella,
Scalia Giusy,
Silvani Alessandra,
Maga Giovanni,
Carraro Fabio,
Botta Maurizio,
Passarella Daniele
Publication year - 2011
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201100304
Subject(s) - chemistry , triazole , cycloaddition , amine gas treating , alkyne , combinatorial chemistry , amide , ring (chemistry) , scaffold , click chemistry , 1,2,3 triazole , stereochemistry , azide , catalysis , organic chemistry , medicine , biomedical engineering
N ‐[2‐Methyl‐5‐(triazol‐1‐yl)phenyl]pyrimidin‐2‐amine derivatives were synthesized and evaluated in vitro for their potential use as inhibitors of Bcr‐Abl. The design is based on the bioisosterism between the 1,2,3‐triazole ring and the amide group. The synthesis involves a copper(I)‐catalyzed azide–alkyne cycloaddition (CuAAC) as the key step, with the exclusive production of anti ‐(1,4)‐triazole derivatives. One of the compounds obtained shows general activity similar to that of imatinib; in particular, it was observed to be more effective in decreasing the fundamental function of cdc25A phosphatases in the K‐562 cell line.