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MedKoo CAT#: 407403
CAS#: 1906920-28-2 (BAY598 R-isomer)
Description: BAY-598 R-isomer is the R-isomer of BAY589. BAY-598 R-isomer may be used as a reference compound. BAY-598 is a potent, peptide-competitive chemical probe for SMYD2. BAY-598 has a unique chemotype relative to the current SMYD2 chemical probe LLY-507. BAY-598 inhibits in vitro methylation of p53K370 with IC50 = 27 nM and has more than 100-fold selectivity over other histone methyltransferases and other non-epigenetic targets. BAY-598 inhibits the methylation of p53K370 in cells with IC50 < 1 µM. (Further to this, BAY-598 has properties that are compatible with in vivo experiments.) A control compound, BAY-369, has also been developed. BAY-369 inhibits the in vitro methylation of p53K370 with IC50 > 70 micromolar.
MedKoo Cat#: 407403
Name: BAY-598 R-isomer
CAS#: 1906920-28-2 (BAY598 R-isomer)
Chemical Formula: C22H20Cl2F2N6O3
Exact Mass: 524.0942
Molecular Weight: 525.3378
Elemental Analysis: C, 50.30; H, 3.84; Cl, 13.50; F, 7.23; N, 16.00; O, 9.14
Related CAS #: 1906920-28-2 (BAY598 R-isomer) 1906919-67-2 (BAY598) 1906920-07-7 (BAY598 recamic mixture)
Synonym: BAY-598 R-isomer; BAY 598 R-isomer; BAY598 R-isomer
IUPAC/Chemical Name: (R,E)-N-(1-(N'-cyano-N-(3-(difluoromethoxy)phenyl)carbamimidoyl)-3-(3,4-dichlorophenyl)-4,5-dihydro-1H-pyrazol-4-yl)-N-ethyl-2-hydroxyacetamide
InChi Key: OTTJIRVZJJGFTK-GOSISDBHSA-N
InChi Code: InChI=1S/C22H20Cl2F2N6O3/c1-2-31(19(34)11-33)18-10-32(30-20(18)13-6-7-16(23)17(24)8-13)22(28-12-27)29-14-4-3-5-15(9-14)35-21(25)26/h3-9,18,21,33H,2,10-11H2,1H3,(H,28,29)/t18-/m1/s1
SMILES Code: CCN([C@@H]1CN(N=C1C2=CC(Cl)=C(C=C2)Cl)/C(NC3=CC=CC(OC(F)F)=C3)=N/C#N)C(CO)=O
1: Eggert E, Hillig RC, Koehr S, Stöckigt D, Weiske J, Barak N, Mowat J, Brumby T, Christ CD, Ter Laak A, Lang T, Fernandez-Montalvan AE, Badock V, Weinmann H, Hartung IV, Barsyte-Lovejoy D, Szewczyk M, Kennedy S, Li F, Vedadi M, Brown PJ, Santhakumar V, Arrowsmith CH, Stellfeld T, Stresemann C. Discovery and Characterization of a Highly Potent and Selective Aminopyrazoline-Based in Vivo Probe (BAY-598) for the Protein Lysine Methyltransferase SMYD2. J Med Chem. 2016 May 26;59(10):4578-600. doi: 10.1021/acs.jmedchem.5b01890. PubMed PMID: 27075367; PubMed Central PMCID: PMC4917279.
2: Ahmed H, Duan S, Arrowsmith CH, Barsyte-Lovejoy D, Schapira M. An Integrative Proteomic Approach Identifies Novel Cellular SMYD2 Substrates. J Proteome Res. 2016 Jun 3;15(6):2052-9. doi: 10.1021/acs.jproteome.6b00220. PubMed PMID: 27163177.
