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Structural Consequences of the 1,2,3‐Triazole as an Amide Bioisostere in Analogues of the Cystic Fibrosis Drugs VX‐809 and VX‐770
Author(s) -
Doiron Jake E.,
Le Christina A.,
Bacsa John,
Breton Gary W.,
Martin Kenneth L.,
Aller Stephen G.,
Turlington Mark
Publication year - 2020
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.202000650
Subject(s) - amide , triazole , cystic fibrosis , bioisostere , chemistry , cystic fibrosis transmembrane conductance regulator , stereochemistry , medicine , biochemistry , chemical synthesis , organic chemistry , in vitro
The Cover Feature shows a representation of the subtle structural differences between the trans ‐amide and 1,2,3‐triazole bioisosteres. As amide looks into the mirror and sees triazole, the question arises: do they look alike? Below the cartoon is an X‐ray structure of an amide‐containing cystic fibrosis drug. The atoms in yellow highlight the drug's planar structure. Above the cartoon is an X‐ray structure of the notably less planar triazole analog. The image background is the region of the cystic fibrosis transmembrane conductance regulator (CFTR) in which these drugs bind. A description of the subtle structural differences between the amide and triazole can be found in the Full Paper by Jake E. Doiron, Christina A. Le, Stephen G. Aller, Mark Turlington et al.