compound 2q [PMID: 30986068]   Click here for help

GtoPdb Ligand ID: 10365

Synonyms: example 2-8 [US20150353552]
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 2q is a PI3Kδ selective inhibitor [2]. It is one of the chemical structures that is claimed in Merck and Shanghai Chempartners' patent US20150353552A1 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 100.19
Molecular weight 439.23
XLogP 1.65
No. Lipinski's rules broken 0
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Canonical SMILES CCn1ncc(c1C)c1nc2c(n1C)ncnc2OC1CCN(C1)C(=O)C1CCOCC1
Isomeric SMILES CCn1ncc(c1C)c1nc2c(n1C)ncnc2O[C@H]1CCN(C1)C(=O)C1CCOCC1
InChI InChI=1S/C22H29N7O3/c1-4-29-14(2)17(11-25-29)19-26-18-20(27(19)3)23-13-24-21(18)32-16-5-8-28(12-16)22(30)15-6-9-31-10-7-15/h11,13,15-16H,4-10,12H2,1-3H3/t16-/m0/s1
Immunopharmacology Comments
Compound 2 is selective for PI3Kδ, which is a kinase whose expression is restricted to cells of the immune system and that is a molecular target for the treatment of inflammatory conditions (asthma [4], RA, COPD, SLE [6-7], activated PI3Kδ syndrome [3]) and haematologic malignancies (for example idelalisib is a selective inhibitor of PI3Kδ that is approved as a treatment for B cell cancers) [5]. Inhibition of PI3Kδ is a mechanism that can be used to selectively reduce phosphorylation and activation of AKT in immune cells, as an alternative to direct AKT inhibition that woiuld affect a much wider range of cells and tissues.