compound 25 [PMID: 31260299]   Click here for help

GtoPdb Ligand ID: 10428

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 25 is a potent, selective and reversible inhibitor of Bruton's tyrosine kinase (BTK) [2]. It is built on a 4-aminoquinoline scaffold, and has improved drug-like properties (aqueous solubility, potency and stability) compared to previously reported cinnoline scaffold compounds [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 119.91
Molecular weight 351.11
XLogP 2.77
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc2cn[nH]c2cc1c1ccc(c2c1ncc(c2N)C(=O)N)F
Isomeric SMILES COc1cc2cn[nH]c2cc1c1ccc(c2c1ncc(c2N)C(=O)N)F
InChI InChI=1S/C18H14FN5O2/c1-26-14-4-8-6-23-24-13(8)5-10(14)9-2-3-12(19)15-16(20)11(18(21)25)7-22-17(9)15/h2-7H,1H3,(H2,20,22)(H2,21,25)(H,23,24)
Immunopharmacology Comments
Novel BTK inhibitors, like compound 25 are being investigated for their potential to treat autoimmune inflammation [2]. Compound 25 has demonstrated the ability to reduce paw swelling in a rodent collagen-induced arthritis model, which is indicative of potential efficacy in human rheumatoid arthritis. Such compounds are being developed as less toxic alternatives to existing clinically used BTK inhibitors like ibrutinib and acalabrutinib, which would make use in diseases other than cancer more feasible.