title: The glycogen phosphorylase inhibitor 2-(3-benzylamino-2-oxo-1,2-dihydropyridin-1-yl)-N-(3,4-dichlorobenzyl)acetamide.
abstract: The molecular structure of the title compound, C21H19Cl2N3O2, a potent glycogen phosphorylase a (GPa) inhibitor (IC50 of 6.3 µM), consists of four distinct conjugated π systems separated by rotatable C-C bonds at the methylene groups. Molecules are linked into dimers disposed about a crystallographic centre of symmetry through a cyclic N-H...O hydrogen-bonding motif [graph set R2(2)(10)]. These dimers are further connected along the crystallographic c axis by N-H...O hydrogen bonding between the amide groups [graph set C(4)]. A comparison of this structure with that of the monohydrate of the significantly less active analogue (S)-2-(3-benzylamino-2-oxo-1,2-dihydropyridin-1-yl)-N-(2-hydroxy-1-phenylethyl)acetamide (IC50 of 120 µM) is presented.
authors.affiliation: School of Biomolecular and Physical Sciences, Griffith University, Nathan, Brisbane 4111, Australia.
authors.forename: Inessa
authors.initials: I
authors.lastname: Popova
authors.forename: Peter C
authors.initials: PC
authors.lastname: Healy
authors.forename: Wendy A
authors.initials: WA
authors.lastname: Loughlin
authors.forename: N David
authors.initials: ND
authors.lastname: Karis
authors.forename: Ian D
authors.initials: ID
authors.lastname: Jenkins
mesh_terms: D000081:Acetamides / Q000737:chemistry* / Q000494:pharmacology; D001596:Benzylamines / Q000737:chemistry* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000378:metabolism; D024981:Glycogen Phosphorylase / Q000037:antagonists & inhibitors* / Q000737:chemistry* / Q000378:metabolism; D006860:Hydrogen Bonding; D015394:Molecular Structure
chemical_list: C586922:2-(3-benzylamino-2-oxo-1,2-dihydropyridin-1-yl)-N-(3,4-dichlorobenzyl)acetamide; D000081:Acetamides; D001596:Benzylamines; D004791:Enzyme Inhibitors; D024981:Glycogen Phosphorylase
keywords: crystal structure; glycogen phosphorylase inhibitors; pyridone derivatives; structure comparison