JAK inhibitor 20a   Click here for help

GtoPdb Ligand ID: 10147

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Inhibitor 20a represents a novel chemotype for Janus kinase inhibitors; benzo[ c]pyrrolo[2,3- h][1,6]naphthyridin-5-one (BPN) [1]. It was identified using sequential palladium catalysis.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 113.24
Molecular weight 445.18
XLogP 2.34
No. Lipinski's rules broken 0
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Canonical SMILES N#CC1CN(C1)C(=O)C(n1c(=O)c2cc(OC)c(cc2c2c1c1cc[nH]c1nc2)OC)CC
Isomeric SMILES N#CC1CN(C1)C(=O)[C@H](n1c(=O)c2cc(OC)c(cc2c2c1c1cc[nH]c1nc2)OC)CC
InChI InChI=1S/C24H23N5O4/c1-4-18(24(31)28-11-13(9-25)12-28)29-21-14-5-6-26-22(14)27-10-17(21)15-7-19(32-2)20(33-3)8-16(15)23(29)30/h5-8,10,13,18H,4,11-12H2,1-3H3,(H,26,27)/t18-/m1/s1
1. Elsayed MSA, Nielsen JJ, Park S, Park J, Liu Q, Kim CH, Pommier Y, Agama K, Low PS, Cushman M. (2018)
Application of Sequential Palladium Catalysis for the Discovery of Janus Kinase Inhibitors in the Benzo[ c]pyrrolo[2,3- h][1,6]naphthyridin-5-one (BPN) Series.
J Med Chem, 61 (23): 10440-10462. [PMID:30460842]