Lassagne, Frederic; Dugueperoux, Camille; Roca, Carlos; Perez, Concepcion; Martinez, Ana; Baratte, Blandine; Robert, Thomas; Ruchaud, Sandrine; Bach, Stephane; Erb, William; Roisnel, Thierry; Mongin, Florence published the artcile< From simple quinoxalines to potent oxazolo[5,4-f]quinoxaline inhibitors of glycogen-synthase kinase 3 (GSK3)>, Quality Control of 6272-25-9, the main research area is oxazoloquinoxaline preparation glycogen synthase kinase inhibition kinetic SAR docking.
2,7-Disubstituted oxazolo[5,4-f]quinoxalines were synthesized from 6-amino-2-chloroquinoxaline in four steps (iodination at C5, substitution of the chloro group, amidation and copper-catalyzed cyclization) affording 28 to 44% overall yields. 2,8-Disubstituted oxazolo[5,4-f]quinoxaline was similarly obtained from 6-amino-3-chloroquinoxaline (39% overall yield). For the synthesis of other oxazolo[5,4-f]quinoxalines, amidation was rather performed before substitution; moreover, time-consuming purification steps were avoided between the amines and the final products (38 to 54% overall yields). Finally, a more efficient method involving merging of the last two steps in a sequential process was developed to access more derivatives (37 to 65% overall yields). Most of the oxazolo[5,4-f]quinoxalines were evaluated for their activity on a panel of protein kinases, and a few 2,8-disubstituted derivatives proved to inhibit GSK3 kinase. While experiments showed an ATP-competitive inhibition on GSK3β, structure-activity relationships allowed us to identify 2-(3-pyridyl)-8-(thiomorpholino)oxazolo[5,4-f]quinoxaline as the most potent inhibitor with an IC50 value of about 5 nM on GSK3α.
Organic & Biomolecular Chemistry published new progress about Amidation. 6272-25-9 belongs to class quinoxaline, and the molecular formula is C8H4ClN3O2, Quality Control of 6272-25-9.
Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider