74115-13-2Relevant articles and documents
Synthesis of novel 7-substituted pyrido[2′,3′:4,5]furo[3,2-d] pyrimidin-4-amines and their N-aryl analogues and evaluation of their inhibitory activity against Ser/Thr kinases
Deau, Emmanuel,Loidreau, Yvonnick,Marchand, Pascal,Nourrisson, Marie-Renee,Loaec, Nadege,Meijer, Laurent,Levacher, Vincent,Besson, Thierry
, p. 6784 - 6788 (2014/01/06)
The efficient synthesis of 7-substituted pyrido[2′,3′:4,5] furo[3,2-d]pyrimidin-4-amines and their N-aryl analogues is described. 3,5-Dibromopyridine was converted into 3-amino-6-bromofuro[3,2-b]pyridine-2- carbonitrile intermediate which was formylated with DMFDMA. Functionalization at position 7 of the tricyclic scaffold was accomplished, before or after cyclisation step, by palladium-catalyzed Suzuki-Miyaura cross-coupling while the pyrimidin-4-amines and N-aryl counterparts were synthesized by microwave-assisted formamide degradation and Dimroth rearrangement, respectively. The final products were evaluated for their potent inhibition of a series of five Ser/Thr kinases (CDK5/p25, CK1δ/ε, CLK1, DYRK1A, GSK3α/β). Compound 35 showed the best inhibitory activity with an IC50 value of 49 nM and proved to be specific to CLK1 among the panel of tested kinases.
A convenient route to functionalized 3-amino-6-bromofuro[3,2-b]pyridine-2-carboxamides
Bretéché, Anne,Marchand, Pascal,Nourrisson, Marie-Renée,De Nanteuil, Guillaume,Duflos, Muriel
experimental part, p. 4490 - 4494 (2010/07/06)
An efficient synthesis of 3-amino-6-bromofuro[3,2-b]pyridine-2-carboxamides is described via the formation of 3-amino-6-bromofuro[3,2-b]pyridine-2-carbonitrile. Functionalization of the amino group at position 3 of the heterocycle will be discussed.
An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin- and pyrimidin-2-yl acetate
Morgentin, Rémy,Jung, Frédéric,Lamorlette, Maryannick,Maudet, Micka?l,Ménard, Morgan,Plé, Patrick,Pasquet, Georges,Renaud, Fabrice
experimental part, p. 757 - 764 (2009/04/07)
The synthesis of methyl 2-(5-hydroxy-3-methoxypyridin-2-yl)acetate and alkyl 2-(5-hydroxypyrimidin-2-yl)acetate is described. Methodology for an efficient access to 5-hydroxy-pyridin- and pyrimidin-2-yl acetate cores has been developed. Based on the difference in halogen reactivity, 5-bromo-2-chloropyridine and its pyrimidine analogue were functionalized judiciously by SNAr and palladium-catalyzed reactions. The outlined strategy provides a high-yielding route suitable for large-scale synthesis of these compounds as well as paves the way for a potential rapid access to other heterocyclic analogues.