compound 5d [PMID: 31335136]   

GtoPdb Ligand ID: 10441

Synonyms: Example 59 [WO2018121550]
Compound class: Synthetic organic
Comment: Compound 5d is a potent, 4-methylquinazoline-based pan-PI3K inhibitor [1]. It is one of the examples claimed in patent WO2018121550A1 from the Institute of Pharmaceutical Research, Chinese Academy of Medical Sciences [2].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 120.91
Molecular weight 542.14
XLogP 3.89
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COc1ncc(cc1NS(=O)(=O)c1ccc(cc1F)F)c1cc(OCC2(C)COC2)c2c(c1)c(C)ncn2
Isomeric SMILES COc1ncc(cc1NS(=O)(=O)c1ccc(cc1F)F)c1cc(OCC2(C)COC2)c2c(c1)c(C)ncn2
InChI InChI=1S/C26H24F2N4O5S/c1-15-19-6-16(8-22(24(19)31-14-30-15)37-13-26(2)11-36-12-26)17-7-21(25(35-3)29-10-17)32-38(33,34)23-5-4-18(27)9-20(23)28/h4-10,14,32H,11-13H2,1-3H3
InChI Key CPUXOJVJEJZOSP-UHFFFAOYSA-N
Bioactivity Comments
Compound 5d blocks phosphorylation of the main effectors downstream of PI3K [1]. It potently inhibits proliferation of mouse MLg2908 lung fibroblasts (IC50 5 nM). Compound 5d was found to inhibit only PI3Ks in panel of 97 kinases.
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta Hs Inhibitor Inhibition 9.1 pIC50 - 1
pIC50 9.1 (IC50 7x10-10 M) [1]
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha Hs Inhibitor Inhibition 9.1 pIC50 - 1
pIC50 9.1 (IC50 8.7x10-10 M) [1]
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta Hs Inhibitor Inhibition 9.0 pIC50 - 1
pIC50 9.0 (IC50 1.1x10-9 M) [1]
phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma Hs Inhibitor Inhibition 8.8 pIC50 - 1
pIC50 8.8 (IC50 1.6x10-9 M) [1]