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
1. Achab AA, Altman MD, Deng Y, Guzi T, Kattar S, Katz JD, Methot JL, Zhou H, McGowan M, Christopher MP et al.. (2015)
Purine inhibitors of human phosphatidylinositol 3-kinase delta.
Patent number: US20150353552A1. Assignee: SHANGHAI CHEMPARTNER CO Ltd., Merck Sharp and Dohme Corp. Priority date: 16/11/2012. Publication date: 10/12/2015.
2. Methot JL, Zhou H, Kattar SD, McGowan MA, Wilson K, Garcia Y, Deng Y, Altman M, Fradera X, Lesburg C et al.. (2019)
Structure Overhaul Affords a Potent Purine PI3Kδ Inhibitor with Improved Tolerability.
J Med Chem, 62 (9): 4370-4382. [PMID:30986068]
3. Michalovich D, Nejentsev S. (2018)
Activated PI3 Kinase Delta Syndrome: From Genetics to Therapy.
Front Immunol, 9: 369. [PMID:29535736]
4. Sriskantharajah S, Hamblin N, Worsley S, Calver AR, Hessel EM, Amour A. (2013)
Targeting phosphoinositide 3-kinase δ for the treatment of respiratory diseases.
Ann N Y Acad Sci, 1280: 35-9. [PMID:23551101]
5. Stark AK, Sriskantharajah S, Hessel EM, Okkenhaug K. (2015)
PI3K inhibitors in inflammation, autoimmunity and cancer.
Curr Opin Pharmacol, 23: 82-91. [PMID:26093105]
6. Suárez-Fueyo A, Barber DF, Martínez-Ara J, Zea-Mendoza AC, Carrera AC. (2011)
Enhanced phosphoinositide 3-kinase δ activity is a frequent event in systemic lupus erythematosus that confers resistance to activation-induced T cell death.
J Immunol, 187 (5): 2376-85. [PMID:21810603]
7. Suárez-Fueyo A, Rojas JM, Cariaga AE, García E, Steiner BH, Barber DF, Puri KD, Carrera AC. (2014)
Inhibition of PI3Kδ reduces kidney infiltration by macrophages and ameliorates systemic lupus in the mouse.
J Immunol, 193 (2): 544-54. [PMID:24935930]