CEP-33779   

GtoPdb Ligand ID: 9387

Synonyms: CEP33779 | compound 29 [PMID: 22594690]
Compound class: Synthetic organic
Comment: CEP-33779 is a selective, orally bioavailable inhibitor of Janus kinase 2 (JAK2) with anti-tumour activity [1]. Selectivity for JAK2 over JAK3 is sought to minimise the risk of immune suppression associated with JAK3 inhibition.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 91.22
Molecular weight 462.18
XLogP 3.85
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CN1CCN(CC1)c1cccc(c1)Nc1nn2c(n1)c(ccc2)c1ccc(cc1)S(=O)(=O)C
Isomeric SMILES CN1CCN(CC1)c1cccc(c1)Nc1nn2c(n1)c(ccc2)c1ccc(cc1)S(=O)(=O)C
InChI InChI=1S/C24H26N6O2S/c1-28-13-15-29(16-14-28)20-6-3-5-19(17-20)25-24-26-23-22(7-4-12-30(23)27-24)18-8-10-21(11-9-18)33(2,31)32/h3-12,17H,13-16H2,1-2H3,(H,25,27)
InChI Key RFZKSQIFOZZIAQ-UHFFFAOYSA-N
References
1. Dugan BJ, Gingrich DE, Mesaros EF, Milkiewicz KL, Curry MA, Zulli AL, Dobrzanski P, Serdikoff C, Jan M, Angeles TS et al.. (2012)
A selective, orally bioavailable 1,2,4-triazolo[1,5-a]pyridine-based inhibitor of Janus kinase 2 for use in anticancer therapy: discovery of CEP-33779.
J. Med. Chem., 55 (11): 5243-54. [PMID:22594690]