Yngve U., Söderman P., Svensson M., Rosqvist S., Arvidsson P.I.
Medicinal Chemistry IScience, CNSP IMed, AstraZeneca RandD Södertälje, SE-151 85 Södertälje, Sweden; Neuroscience IScience, CNSP IMed, AstraZeneca RandD Södertälje, SE-151 85 Södertälje, Sweden; Project Management, CNSP IMed, AstraZeneca RandD Södertälje, SE-151 85 Södertälje, Sweden; Department of Medicinal Chemistry, Uppsala Biomedical Centre, Uppsala University, SE-751 23 Uppsala, Sweden; School of Pharmacy and Pharmacology, Westville Campus, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South Africa
Yngve, U., Medicinal Chemistry IScience, CNSP IMed, AstraZeneca RandD Södertälje, SE-151 85 Södertälje, Sweden; Söderman, P., Medicinal Chemistry IScience, CNSP IMed, AstraZeneca RandD Södertälje, SE-151 85 Södertälje, Sweden; Svensson, M., Medicinal Chemistry IScience, CNSP IMed, AstraZeneca RandD Södertälje, SE-151 85 Södertälje, Sweden; Rosqvist, S., Neuroscience IScience, CNSP IMed, AstraZeneca RandD Södertälje, SE-151 85 Södertälje, Sweden; Arvidsson, P.I., Project Management, CNSP IMed, AstraZeneca RandD Södertälje, SE-151 85 Södertälje, Sweden, Department of Medicinal Chemistry, Uppsala Biomedical Centre, Uppsala University, SE-751 23 Uppsala, Sweden, School of Pharmacy and Pharmacology, Westville Campus, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South Africa
In this study, we explored the effect of bioisostere replacement in a series of glycogen synthase kinase 3 (GSK3) inhibitors based on the imidazopyridine core. The synthesis and biological evaluation of a number of novel sulfonamide, 1,2,4-oxadiazole, and thiazole derivates as amide bioisosteres, as well as a computational rationalization of the obtained results are reported. © 2012 Verlag Helvetica Chimica Acta AG, Zürich.
1,2,4 oxadiazole derivative; 2 [4 (morpholin 4 ylmethyl)phenyl] 7 [2 (piperidin 1 yl) 1,3 thiazol 4 yl] 3h imidazo[4,5 b]pyridine hydrochloride; 2 [4 (morpholin 4 ylmethyl)phenyl] 7 [3 (propan 2 yl) 1,2,4 oxadiazol 5 yl] 3h imidazo[4,5 b]pyridine hydrochloride; 2 [4 (morpholin 4 ylmethyl)phenyl] 7 [3 (pyridin 3 yl) 1,2,4 oxadiazol 5 yl] 3h imidazo[4,5 b]pyridine hydrochloride; 3 [4[[2 [4 (trifluoromethyl)phenyl] 3h imidazo[4,5 b]pyridin 7 yl]sulfonyl]piperazin 1 yl]propanenitrile; 7 [2 (morpholin 4 yl) 1,3 thiazol 4 yl] 2 [4 (trifluoromethyl)phenyl] 3h imidazo[4,5 b]pyridine hydrochloride; 7 [2 (piperidin 1 yl) 1,3 thiazol 4 yl] 2 [4 (trifluoromethyl)phenyl] 3h imidazo[4,5 b]pyridine hydrochloride; 7 [3 (2 methoxyethyl) 1,2,4 oxadiazol 5 yl] 2 [4 (morpholin 4 ylmethyl)phenyl] 3h imidazo[4,5 b]pyridine hydrochloride; amide; glycogen synthase kinase 3 inhibitor; imidazopyridine derivative; n (2 hydroxy 1 phenylethyl) 2 [4 (trifluoromethyl)phenyl] 3h imidazo[4,5 b]pyridine 7 sulfonamide hydrochloride; n (2 methoxyethyl) n methyl 2 [4 (trifluoromethyl)phenyl] 3h imidazo[4,5 b]pyridine 7 sulfonamide hydrochloride; n (3 methoxypropyl) 2 [4 (trifluoromethyl)phenyl] 3h imidazo[4,5 b]pyridine 7 sulfonamide hydrochloride; n [3 (1h imidazol 1 yl)propyl] 2 [4 (trifluoromethyl)phenyl] 3h imidazo[4,5 b]pyridine 7 sulfonamide hydrochloride; n cyclopentyl 2 [4 (trifluoromethyl)phenyl] 3h imidazo[4,5 b]pyridine 7 sulfonamide hydrochloride; thiazole derivative; unclassified drug; article; drug design; drug potency; drug screening; drug stability; drug structure; drug synthesis; drug transformation; human; human cell; Drug Design; Glycogen Synthase Kinase 3; Humans; Molecular Dynamics Simulation; Oxadiazoles; Pyridines; Sulfonamides; Thiazoles