VVD-118313

VVD-118313
Identifiers
	IUPAC name 1-[(3S)-3-(3,4-dichlorophenyl)piperidin-1-yl]-3-[(3R)-1-methylsulfonylpyrrolidin-3-yl]prop-2-yn-1-one;
CAS Number	2875046-27-6;
PubChem CID	168008613;
ChemSpider	123963146;
Chemical and physical data
Formula	C19H22Cl2N2O3S
Molar mass	429.36 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CS(=O)(=O)N1CC[C@@H](C1)C#CC(=O)N2CCC[C@H](C2)C3=CC(=C(C=C3)Cl)Cl;
	InChI InChI=1S/C19H22Cl2N2O3S/c1-27(25,26)23-10-8-14(12-23)4-7-19(24)22-9-2-3-16(13-22)15-5-6-17(20)18(21)11-15/h5-6,11,14,16H,2-3,8-10,12-13H2,1H3/t14-,16+/m0/s1; Key:OUPVMVHXMWBFDP-GOEBONIOSA-N;

VVD-118313 is a chemical compound which acts as a potent and selective negative allosteric modulator of JAK1, and was developed for research into the treatment of inflammatory diseases, especially chronic inflammation involved in the development of cancer.^[1]^[2]^[3]^[4]

References

^ Kavanagh ME, Horning BD, Khattri R, Roy N, Lu JP, Whitby LR, et al. (December 2022). "Selective inhibitors of JAK1 targeting an isoform-restricted allosteric cysteine". Nature Chemical Biology. 18 (12): 1388–1398. doi:10.1038/s41589-022-01098-0. PMC 7614775. PMID 36097295.
^ Silvennoinen O, Haikarainen T, Virtanen A (December 2022). "Aiming for the pocket". Nature Chemical Biology. 18 (12): 1296–1297. doi:10.1038/s41589-022-01120-5. PMID 36097296.
^ Caveney NA, Saxton RA, Waghray D, Glassman CR, Tsutsumi N, Hubbard SR, et al. (March 2023). "Structural basis of Janus kinase trans-activation". Cell Reports. 42 (3): 112201. doi:10.1016/j.celrep.2023.112201. PMC 10180219. PMID 36867534.
^ Henry SP, Jorgensen WL (August 2023). "Progress on the Pharmacological Targeting of Janus Pseudokinases". Journal of Medicinal Chemistry. 66 (16): 10959–10990. doi:10.1021/acs.jmedchem.3c00926. PMID 37578217.

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[1] Kavanagh ME, Horning BD, Khattri R, Roy N, Lu JP, Whitby LR, et al. (December 2022). "Selective inhibitors of JAK1 targeting an isoform-restricted allosteric cysteine". Nature Chemical Biology. 18 (12): 1388–1398. doi:10.1038/s41589-022-01098-0. PMC 7614775. PMID 36097295.

[pmid36097296-2] Silvennoinen O, Haikarainen T, Virtanen A (December 2022). "Aiming for the pocket". Nature Chemical Biology. 18 (12): 1296–1297. doi:10.1038/s41589-022-01120-5. PMID 36097296.

[3] Caveney NA, Saxton RA, Waghray D, Glassman CR, Tsutsumi N, Hubbard SR, et al. (March 2023). "Structural basis of Janus kinase trans-activation". Cell Reports. 42 (3): 112201. doi:10.1016/j.celrep.2023.112201. PMC 10180219. PMID 36867534.

[4] Henry SP, Jorgensen WL (August 2023). "Progress on the Pharmacological Targeting of Janus Pseudokinases". Journal of Medicinal Chemistry. 66 (16): 10959–10990. doi:10.1021/acs.jmedchem.3c00926. PMID 37578217.

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Identifiers

IUPAC name 1-[(3S)-3-(3,4-dichlorophenyl)piperidin-1-yl]-3-[(3R)-1-methylsulfonylpyrrolidin-3-yl]prop-2-yn-1-one
CAS Number	2875046-27-6
PubChem CID	168008613
ChemSpider	123963146
Chemical and physical data
Formula	C₁₉H₂₂Cl₂N₂O₃S
Molar mass	429.36 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CS(=O)(=O)N1CC[C@@H](C1)C#CC(=O)N2CCC[C@H](C2)C3=CC(=C(C=C3)Cl)Cl
InChI InChI=1S/C19H22Cl2N2O3S/c1-27(25,26)23-10-8-14(12-23)4-7-19(24)22-9-2-3-16(13-22)15-5-6-17(20)18(21)11-15/h5-6,11,14,16H,2-3,8-10,12-13H2,1H3/t14-,16+/m0/s1 Key:OUPVMVHXMWBFDP-GOEBONIOSA-N

VVD-118313

See also

References