kinase inhibitor 2 [PMID: 30199702]   

GtoPdb Ligand ID: 10081

Compound class: Synthetic organic
Comment: This compound is reported by Compain et al. (2018) as the protein kinase inhibitor component of a β-glucuronidase-responsive albumin-binding prodrug that was designed as a novel cancer therapeutic [1]. The biological activity of inhibitor 2 is blocked when it is incoprorated in the enzyme-responsive prodrug. The active inhibitor is released only in the presence of β-glucuronidase (e.g. as exists in the tumour microenvironment), so should faciliate selective delivery of the drug to the tumour whilst minimising systemic off-target and adverse effects. Compound 2 is a multi-kinase inhibitor with a similar selectivity profile as seliciclib, but with additional potent inhibitory activity at DYRK3 and GSK3.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 106.05
Molecular weight 456.27
XLogP 4.61
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES NC1CCC(CC1)Nc1nc(NCc2ccc(cc2)c2ccccn2)n2c(n1)c(cn2)C(C)C
Isomeric SMILES N[C@@H]1CC[C@H](CC1)Nc1nc(NCc2ccc(cc2)c2ccccn2)n2c(n1)c(cn2)C(C)C
InChI InChI=1S/C26H32N8/c1-17(2)22-16-30-34-24(22)32-25(31-21-12-10-20(27)11-13-21)33-26(34)29-15-18-6-8-19(9-7-18)23-5-3-4-14-28-23/h3-9,14,16-17,20-21H,10-13,15,27H2,1-2H3,(H2,29,31,32,33)/t20-,21-
InChI Key PRJNNPMIUGYOST-MEMLXQNLSA-N
Classification
Compound class Synthetic organic
IUPAC Name
8-(propan-2-yl)-N4-{[4-(pyridin-2-yl)phenyl]methyl}-N2-[(1r,4r)-4-aminocyclohexyl]pyrazolo[1,5-a][1,3,5]triazine-2,4-diamine
Database Links
GtoPdb PubChem SID 375973268
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