MS-275, SNDX-275, MS-27-275, Entinostat

MS-275 (SNDX-275; MS-27-275; Entinostat) preferentially inhibits HDAC 1 compared with HDAC 3 and has little or no effect against HDACs 6 and 8. The amine group of the benzanilide moiety might act as a hydrogen bond donor or could be involved in other electrostatic interactions, which are necessary for inhibitory activity.

IUPAC Name: pyridin-3-ylmethyl 4-(2-aminophenylcarbamoyl)benzylcarbamate
Molecular Weight: 376.42 g/mol
Molecular Formula: C21H20N4O3
SMILES: Nc1ccccc1NC(=O)c2ccc(cc2)CNC(=O)OCc3cccnc3
Canonical SMILES: C1=CC=C(C(=C1)N)NC(=O)C2=CC=C(C=C2)CNC(=O)OCC3=CN=CC=C3
InChIKey Identifier: INVTYAOGFAGBOE-UHFFFAOYSA-N
CAS Number: 209783-80-2
Melting point: 159–160 °C
Solubility: 2 mg/ml in ethanol; 30 mg/ml in DMSO and DMF
2D Molfile: Get the molfile
Synonyms: SNDX-275; MS-27-275; Entinostat

Currently, Entinostat (in combination with azacitidine) is in a clinical phase I/II trials for myelodysplastic syndromes, chronic myelomonocytic leukemia, and acute myeloid leukemia with multilineage dysplasia. This compound (in combination with azacitidine) is also in clinical phase I/II trials for patients with recurrent advanced nonsmall-cell lung cancer.

References:
1) Hu E, Dul E, Sung CM et al (2003) Identification of novel isoform-selective inhibitors within class I histone deacetylases. J Pharmacol Exp Ther 307 (2):720–728
2) Daniel Riester, Christian Hildmann, Andreas Schwienhorst. Histone deacetylase inhibitors—turning epigenic mechanisms of gene regulation into tools of therapeutic intervention in malignant and other diseases. Appl Microbiol Biotechnol (2007) 75:499–514
3) Bouchain G et al. Development of Potential Antitumor Agents. Synthesis and Biological Evaluation of a New Set of Sulfonamide Derivatives as Histone Deacetylase Inhibitors. J. Med. Chem. 2003, 46, 820-830