Z583

Z583
Identifiers
	IUPAC name N-[3-[[6-[[1-(2-methoxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]prop-2-enamide;
CAS Number	2412569-41-4;
PubChem CID	146478990;
Chemical and physical data
Formula	C21H22N8O2
Molar mass	418.461 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COCCN1C=C(C=N1)NC2=NC=C3C=NN(C3=N2)CC4=CC(=CC=C4)NC(=O)C=C;
	InChI InChI=1S/C21H22N8O2/c1-3-19(30)25-17-6-4-5-15(9-17)13-29-20-16(11-24-29)10-22-21(27-20)26-18-12-23-28(14-18)7-8-31-2/h3-6,9-12,14H,1,7-8,13H2,2H3,(H,25,30)(H,22,26,27); Key:BOBFKXIKGHTPJB-UHFFFAOYSA-N;

Z583 (GLXC-26150) is a chemical compound which acts as a potent and highly selective inhibitor of JAK3, and was developed for the treatment of rheumatoid arthritis.^[1]^[2]^[3]^[4]^[5]

References

^ Baillache DJ, Unciti-Broceta A. Recent developments in anticancer kinase inhibitors based on the pyrazolo[3,4-d]pyrimidine scaffold. RSC Med Chem. 2020 Sep 8;11(10):1112-1135. doi:10.1039/d0md00227e PMID 33479617
^ Chen C, Yin Y, Shi G, Zhou Y, Shao S, Wei Y, Wu L, Zhang D, Sun L, Zhang T. A highly selective JAK3 inhibitor is developed for treating rheumatoid arthritis by suppressing γc cytokine-related JAK-STAT signal. Sci Adv. 2022 Aug 19;8(33):eabo4363. doi:10.1126/sciadv.abo4363 PMID 35984890
^ Phillips, R. Novel JAK3-specific inhibitor safe and effective in mouse RA model. Nat Rev Rheumatol 2022; 18: 551. doi:10.1038/s41584-022-00839-8
^ Xue C, Yao Q, Gu X, Shi Q, Yuan X, Chu Q, Bao Z, Lu J, Li L. Evolving cognition of the JAK-STAT signaling pathway: autoimmune disorders and cancer. Signal Transduct Target Ther. 2023 May 19;8(1):204. doi:10.1038/s41392-023-01468-7 PMID 37208335
^ Jensen LT, et al. Allosteric TYK2 inhibition: redefining autoimmune disease therapy beyond JAK1-3 inhibitors. eBioMedicine 2023; 97: 104840. doi:10.1016/j.ebiom.2023.104840

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Identifiers

IUPAC name N-[3-[[6-[[1-(2-methoxyethyl)pyrazol-4-yl]amino]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]phenyl]prop-2-enamide
CAS Number	2412569-41-4
PubChem CID	146478990
Chemical and physical data
Formula	C₂₁H₂₂N₈O₂
Molar mass	418.461 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COCCN1C=C(C=N1)NC2=NC=C3C=NN(C3=N2)CC4=CC(=CC=C4)NC(=O)C=C
InChI InChI=1S/C21H22N8O2/c1-3-19(30)25-17-6-4-5-15(9-17)13-29-20-16(11-24-29)10-22-21(27-20)26-18-12-23-28(14-18)7-8-31-2/h3-6,9-12,14H,1,7-8,13H2,2H3,(H,25,30)(H,22,26,27) Key:BOBFKXIKGHTPJB-UHFFFAOYSA-N