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  • Title: The glycogen phosphorylase inhibitor 2-(3-benzylamino-2-oxo-1,2-dihydropyridin-1-yl)-N-(3,4-dichlorobenzyl)acetamide.
    Author: Popova I, Healy PC, Loughlin WA, Karis ND, Jenkins ID.
    Journal: Acta Crystallogr C; 2013 Nov; 69(Pt 11):1408-10. PubMed ID: 24192198.
    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.
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