Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors

Metal‐Free C3 Hydroxylation of Quinoxalin‐2(1H)‐ones in Water

“…Quinoxaline‐2,3‐dione and their derivatives play an important role in organic synthesis, pharmaceutical chemistry and materials science . Traditionally, N‐functionalized quinoxaline‐2,3‐diones are prepared through base‐promoted condensation reaction between mono N‐substituted 1,2‐diaminobenzenes and oxalyl chloride (or ethyl chloroglyoxalate) (Scheme a) . However, from a practical and eco‐friendly point of view, those procedures still suffer from some drawbacks, such as the difficulties of preparation and isolation of mono N‐substituted substrates, the usage of toxic oxalyl chloride and volatile organic solvent, and harsh reaction conditions.…”

Electrochemical Dehydrogenative Cross‐Coupling of Quinoxalin‐2(1H)‐ones with Amines for the Synthesis of 3‐Aminoquinoxalinones

“…In particular, the 3‐aminoquinoxalinone motif is found widely in bioactive compounds, such as antibacterial, antiviral, anticancer, anti‐diabetic, and anti‐inflammatory agents . Consequently, many synthetic strategies have been developed for the synthesis of 3‐aminoquinoxalinones, the most conventional approaches involving either the construction of the quinoxalin‐2(1 H )‐one heterocycle or the nucleophilic substitution of quinoxalin‐2(1 H )‐one derivatives bearing a halo or other leaving group . The oxidative functionalization of C−H bonds has emerged as an appealing method in organic chemistry, since the prefunctionalization of C−H bonds is avoided.…”

Chapter 12. Inhibition of Glycogen Phosphorylase as a Strategy for the Treatment of Type 2 Diabetes

“…Scientists from Johnson & Johnson 76 have described a series of anilinoquinoxalinone GP inhibitors exemplified by compound 27 (Figure 12.7). Structural changes in the aniline moiety had the most impact on enzyme potency in this series, while changes to the quinoxalinone portion of the template had little effect.…”