The glycogen phosphorylase inhibitor 2‐(3‐benzylamino‐2‐oxo‐1, 2‐dihydropyridin‐1‐yl)‐N‐(3, 4‐dichlorobenzyl)acetamide. (15th November 2013)

• Record Type: Journal Article
• Authors: Popova, Inessa; Healy, Peter C.; Loughlin, Wendy A.; Karis, N. David; Jenkins, Ian D.
• Is Part Of: Acta crystallographica. Volume 69:Part 11(2013:Nov.)
• Page Start: 1408
• Page End: 1410
• Publication Date: 2013-11-15
• Subjects: crystal structure -- pyridone derivatives -- glycogen phosphorylase inhibitors -- structure comparison; Crystallography -- Periodicals; Crystals -- Periodicals; 548.05
• DOI: 10.1107/S0108270113028631
• Languages: English
• ISSNs: 0108-2701

Abstract

Abstract : The molecular structure of the title compound, C21 H19 Cl2 N3 O2, a potent glycogen phosphorylase a (GPa) inhibitor (IC50 of 6.3 µ M ), 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 R 2 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 µ M ) is presented.