VVD-118313

VVD-118313
	File:VVD-118313 structure.png
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;
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[edit]

^ Kavanagh ME, Horning BD, Khattri R, Roy N, Lu JP, Whitby LR, Ye E, Brannon JC, Parker A, Chick JM, Eissler CL, Wong AJ, Rodriguez JL, Rodiles S, Masuda K, Teijaro JR, Simon GM, Patricelli MP, Cravatt BF. Selective inhibitors of JAK1 targeting an isoform-restricted allosteric cysteine. Nat Chem Biol. 2022 Dec;18(12):1388-1398. doi:10.1038/s41589-022-01098-0 PMID 36097295
^ Silvennoinen O, Haikarainen T, Virtanen A. Aiming for the pocket. Nat Chem Biol 2022; 18: 1296–1297 doi:10.1038/s41589-022-01120-5
^ Caveney NA, Saxton RA, Waghray D, Glassman CR, Tsutsumi N, Hubbard SR, Garcia KC. Structural basis of Janus kinase trans-activation. Cell Rep. 2023 Mar 28;42(3):112201. doi:10.1016/j.celrep.2023.112201 PMID 36867534
^ Henry SP, Jorgensen WL. Progress on the Pharmacological Targeting of Janus Pseudokinases. J Med Chem. 2023 Aug 24;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, Ye E, Brannon JC, Parker A, Chick JM, Eissler CL, Wong AJ, Rodriguez JL, Rodiles S, Masuda K, Teijaro JR, Simon GM, Patricelli MP, Cravatt BF. Selective inhibitors of JAK1 targeting an isoform-restricted allosteric cysteine. Nat Chem Biol. 2022 Dec;18(12):1388-1398. doi:10.1038/s41589-022-01098-0 PMID 36097295

[2] Silvennoinen O, Haikarainen T, Virtanen A. Aiming for the pocket. Nat Chem Biol 2022; 18: 1296–1297 doi:10.1038/s41589-022-01120-5

[3] Caveney NA, Saxton RA, Waghray D, Glassman CR, Tsutsumi N, Hubbard SR, Garcia KC. Structural basis of Janus kinase trans-activation. Cell Rep. 2023 Mar 28;42(3):112201. doi:10.1016/j.celrep.2023.112201 PMID 36867534

[4] Henry SP, Jorgensen WL. Progress on the Pharmacological Targeting of Janus Pseudokinases. J Med Chem. 2023 Aug 24;66(16):10959-10990. doi:10.1021/acs.jmedchem.3c00926 PMID 37578217

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