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 (October 2020). "Recent developments in anticancer kinase inhibitors based on the pyrazolo[3,4-d]pyrimidine scaffold". RSC Medicinal Chemistry. 11 (10): 1112–1135. doi:10.1039/d0md00227e. PMC 7652001. PMID 33479617.
^ Chen C, Yin Y, Shi G, Zhou Y, Shao S, Wei Y, et al. (August 2022). "A highly selective JAK3 inhibitor is developed for treating rheumatoid arthritis by suppressing γc cytokine-related JAK-STAT signal". Science Advances. 8 (33): eabo4363. Bibcode:2022SciA....8O4363C. doi:10.1126/sciadv.abo4363. PMC 9390995. PMID 35984890.
^ Phillips R (October 2022). "Novel JAK3-specific inhibitor safe and effective in mouse RA model". Nature Reviews. Rheumatology. 18 (10): 551. doi:10.1038/s41584-022-00839-8. PMID 36071217.
^ Xue C, Yao Q, Gu X, Shi Q, Yuan X, Chu Q, et al. (May 2023). "Evolving cognition of the JAK-STAT signaling pathway: autoimmune disorders and cancer". Signal Transduction and Targeted Therapy. 8 (1): 204. doi:10.1038/s41392-023-01468-7. PMC 10196327. PMID 37208335.
^ Jensen LT, Attfield KE, Feldmann M, Fugger L (November 2023). "Allosteric TYK2 inhibition: redefining autoimmune disease therapy beyond JAK1-3 inhibitors". eBioMedicine. 97: 104840. doi:10.1016/j.ebiom.2023.104840. PMC 10589750. PMID 37863021.

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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