Discovery of a potent CDK2 inhibitor with a novel binding mode, using virtual screening and initial, structure-guided lead scoping.

Article Details

Citation

Richardson CM, Nunns CL, Williamson DS, Parratt MJ, Dokurno P, Howes R, Borgognoni J, Drysdale MJ, Finch H, Hubbard RE, Jackson PS, Kierstan P, Lentzen G, Moore JD, Murray JB, Simmonite H, Surgenor AE, Torrance CJ

Discovery of a potent CDK2 inhibitor with a novel binding mode, using virtual screening and initial, structure-guided lead scoping.

Bioorg Med Chem Lett. 2007 Jul 15;17(14):3880-5. Epub 2007 May 6.

PubMed ID
17570665 [ View in PubMed
]
Abstract

Virtual screening against a pCDK2/cyclin A crystal structure led to the identification of a potent and novel CDK2 inhibitor, which exhibited an unusual mode of interaction with the kinase binding motif. With the aid of X-ray crystallography and modelling, a medicinal chemistry strategy was implemented to probe the interactions seen in the crystal structure and to establish SAR. A fragment-based approach was also considered but a different, more conventional, binding mode was observed. Compound selectivity against GSK-3beta was improved using a rational design strategy, with crystallographic verification of the CDK2 binding mode.

DrugBank Data that Cites this Article

Polypeptides
NameUniProt ID
Cyclin-dependent kinase 2P24941Details
Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
4-{5-[(1Z)-1-(2-IMINO-4-OXO-1,3-THIAZOLIDIN-5-YLIDENE)ETHYL]-2-FURYL}BENZENESULFONAMIDECyclin-dependent kinase 2IC 50 (nM)307.522Details
4-{5-[(Z)-(2-Imino-4-Oxo-1,3-Thiazolidin-5-Ylidene)methyl]-2-Furyl}-N-MethylbenzenesulfonamideCyclin-dependent kinase 2IC 50 (nM)1207.522Details
4-{5-[(Z)-(2-IMINO-4-OXO-1,3-THIAZOLIDIN-5-YLIDENE)METHYL]FURAN-2-YL}-2-(TRIFLUOROMETHYL)BENZENESULFONAMIDECyclin-dependent kinase 2IC 50 (nM)6107.522Details
4-{5-[(Z)-(2-Imino-4-Oxo-1,3-Thiazolidin-5-Ylidene)methyl]furan-2-Yl}benzenesulfonamideCyclin-dependent kinase 2IC 50 (nM)1807.522Details
4-{5-[(Z)-(2-IMINO-4-OXO-1,3-THIAZOLIDIN-5-YLIDENE)METHYL]FURAN-2-YL}BENZOIC ACIDCyclin-dependent kinase 2IC 50 (nM)470007.522Details
4-{5-[(Z)-(2,4-DIOXO-1,3-THIAZOLIDIN-5-YLIDENE)METHYL]FURAN-2-YL}BENZENESULFONAMIDECyclin-dependent kinase 2IC 50 (nM)270007.522Details