Synthesis of (benzimidazol-2-yl)aniline derivatives as glycogen phosphorylase inhibitors. Issue 21 (1st November 2016)

• Record Type: Journal Article
• Authors: Galal, Shadia A.; Khattab, Muhammad; Andreadaki, Fotini; Chrysina, Evangelia D.; Praly, Jean-Pierre; Ragab, Fatma A.F.; El Diwani, Hoda I.
• Is Part Of: Bioorganic & medicinal chemistry. Volume 24:Issue 21(2016)
• Page Start: 5423
• Page End: 5430
• Publication Date: 2016-11-01
• Subjects: Benzimidazole -- Heterocycles -- Glycogen phosphorylase -- Enzyme inhibition; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2016.08.069
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: A series of (benzimidazol-2-yl)-aniline (1 ) derivatives has been synthesized and evaluated as glycogen phosphorylase (GP) inhibitors. Kinetics studies revealed that compounds displaying a lateral heterocyclic residue with several heteroatoms (series 3 and 5) exhibited modest inhibitory properties with IC50 values in the 400–600 μM range. Arylsulfonyl derivatives7 (Ar: phenyl) and9 (Ar: o -nitrophenyl) of1 exhibited the highest activity (series 2) among the studied compounds (IC50 324 μM and 357 μM, respectively) with stronger effect than the p -tolyl analogue8 .