title: Alpha-cyano-N-(2,5-dibromophenyl)-beta-hydroxybut-2-enamide.
abstract: The title compound, C11H8Br2N2O2 (LFM-A13), is the first reported BTK-specific tyrosine kinase inhibitor and the first antileukemic agent targeting BTK (Bruton's tyrosine kinase). The crystal structure showed that the molecule adopts an approximately planar conformation aided by an intramolecular hydrogen bond formed between the hydroxyl group and the amide carbonyl group. The dihedral angle between the phenyl ring and the plane defined by the N-C-C=C-CH3 group is 8.2 (6) degrees. The crystal packing shows an additional weak intermolecular hydrogen bond between the hydroxyl group and the amide carbonyl-O atom of the centrosymmetrically related molecule.
authors.affiliation: Parker Hughes Cancer Center, Drug Discovery Program, Hughes Institute, St Paul, MN 55113, USA.
authors.forename: S
authors.initials: S
authors.lastname: Ghosh
authors.forename: F M
authors.initials: FM
authors.lastname: Uckun
mesh_terms: D000077329:Agammaglobulinaemia Tyrosine Kinase; D000577:Amides / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors
chemical_list: D000577:Amides; D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; C118451:LFM A13; D009570:Nitriles; D011505:Protein-Tyrosine Kinases; D000077329:Agammaglobulinaemia Tyrosine Kinase