(3S,4R)-Tofacitinib - CAS 1092578-48-7
Catalog number: 1092578-48-7
Category: Inhibitor
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Molecular Formula:
C16H20N6O
Molecular Weight:
312.37
COA:
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Targets:
JAK
Description:
Tofacitinib is a novel inhibitor of JAK3 with IC50 of 1 nM, 20- to 100-fold less potent against JAK2 and JAK1.
Purity:
>98%
Synonyms:
CP-690550 citrate; CP690550 citrate; CP690550 citrate
MSDS:
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InChIKey:
UJLAWZDWDVHWOW-DGCLKSJQSA-N
InChI:
InChI=1S/C16H20N6O/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16-12-4-7-18-15(12)19-10-20-16/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20)/t11-,13-/m1/s1
Canonical SMILES:
CC1CCN(CC1N(C)C2=NC=NC3=C2C=CN3)C(=O)CC#N
1.Examining the chirality, conformation and selective kinase inhibition of 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile (CP-690,550).
Jiang JK1, Ghoreschi K, Deflorian F, Chen Z, Perreira M, Pesu M, Smith J, Nguyen DT, Liu EH, Leister W, Costanzi S, O'Shea JJ, Thomas CJ. J Med Chem. 2008 Dec 25;51(24):8012-8. doi: 10.1021/jm801142b.
Here, we examine the significance that stereochemistry plays within the clinically relevant Janus kinase 3 (Jak3) inhibitor 1 (CP-690,550). A synthesis of all four enantiopure stereoisomers of the drug was carried out and an examination of each compound revealed that only the enantiopure 3R,4R isomer was capable of blocking Stat5 phosphorylation (Jak3 dependent). Each compound was profiled across a panel of over 350 kinases, which revealed a high level of selectivity for the Jak family kinases for these related compounds. Each stereoisomer retained a degree of binding to Jak3 and Jak2 and the 3R,4S and 3S,4R stereoisomers were further revealed to have binding affinity for selected members of the STE7 and STE20 subfamily of kinases. Finally, an appraisal of the minimum energy conformation of each stereoisomer and molecular docking at Jak3 was performed in an effort to better understand each compounds selectivity and potency profiles.
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