CH...O and CH...N hydrogen bonds in ligand design: a novel quinazolin-4-ylthiazol-2-ylamine protein kinase inhibitor.
Aryl CH hydrogen bonds play an important role in the binding of several analogues of a pyrazol-3-ylquinazolin-4-ylamine inhibitor of glycogen synthase kinase 3 (GSK3). Understanding the importance of these CH...O and CH...N hydrogen bonds allowed the design of a novel quinazolin-4-ylthiazol-2-ylamine inhibitor of GSK3 with a structurally confirmed CH...O hydrogen bond to the protein.
Pierce
Albert C
AC
Vertex Pharmaceuticals, Inc., 130 Waverly Street, Cambridge, Massachusetts 02139, USA. al_pierce@vrtx.com
ter Haar
Ernst
E
Binch
Hayley M
HM
Kay
David P
DP
Patel
Sanjay R
SR
Li
Pan
P
D015195:Drug Design; D038362:Glycogen Synthase Kinase 3 / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D006860:Hydrogen Bonding; D007536:Isomerism; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D008024:Ligands; D011799:Quinazolines; D013844:Thiazoles; D038362:Glycogen Synthase Kinase 3