209971-49-3Relevant academic research and scientific papers
Structure guided optimization of a fragment hit to imidazopyridine inhibitors of PI3K
Pecchi, Sabina,Ni, Zhi-Jie,Han, Wooseok,Smith, Aaron,Lan, Jiong,Burger, Matthew,Merritt, Hanne,Wiesmann, Marion,Chan, John,Kaufman, Susan,Knapp, Mark S.,Janssen, Johanna,Huh, Kay,Voliva, Charles F.
supporting information, p. 4652 - 4656 (2013/08/23)
PI3 kinases are a family of lipid kinases mediating numerous cell processes such as proliferation, migration and differentiation. The PI3 Kinase pathway is often de-regulated in cancer through PI3Kα overexpression, gene amplification, mutations and PTEN p
Fragment based discovery of a novel and selective PI3 kinase inhibitor
Hughes, Samantha J.,Millan, David S.,Kilty, Iain C.,Lewthwaite, Russell A.,Mathias, John P.,Reilly, Mark A.O.,Pannifer, Andrew,Phelan, Anne,Stühmeier, Frank,Baldock, Darren A.,Brown, David G.
scheme or table, p. 6586 - 6590 (2011/12/04)
We report the use of fragment screening and fragment based drug design to develop a PI3c kinase fragment hit into a lead. Initial fragment hits were discovered by high concentration biochemical screening, followed by a round of virtual screening to identify additional ligand efficient fragments. These were developed into potent and ligand efficient lead compounds using structure guided fragment growing and merging strategies. This led to a potent, selective, and cell permeable PI3c kinase inhibitor with good metabolic stability that was useful as a preclinical tool compound.
6-Substituted 2-(N-trifluoroacetylamino)imidazopyridines induce cell cycle arrest and apoptosis in SK-LU-1 human cancer cell line
Martínez-Urbina, Miguel Angel,Zentella, Alejandro,Vilchis-Reyes, Miguel Angel,Guzmán, ángel,Vargas, Omar,Ramírez Apan, María Teresa,Ventura Gallegos, José Luis,Díaz, Eduardo
experimental part, p. 1211 - 1219 (2010/05/02)
A series of 6-substituted 2-(N-trifluoroacetylamino)imidazopyridines have been synthesized and their bioactivities were evaluated. Compounds 6a, 6c, and 11a were the most active compounds with modest cytotoxic activity against six human cancer cell lines U251 (glioma), PC-3 (prostate), K-562 (leukemia), HCT-15 (colon), MCF7 (breast) and SK-LU-1 (lung). The cell cycle analysis showed that compounds 6a, 6c, and 11a induce a G2/M phase cell cycle arrest on SK-LU-1 cell line where inhibition of CDK-1 and CDK-2 may be implicated.
Structure-based design of a new class of highly selective aminoimidazo[1,2-a]pyridine-based inhibitors of cyclin dependent kinases
Hamdouchi, Chafiq,Zhong, Boyu,Mendoza, Jose,Collins, Elizabeth,Jaramillo, Carlos,De Diego, Jose Eugenio,Robertson, Daniel,Spencer, Charles D.,Anderson, Bryan D.,Watkins, Scott A.,Zhang, Faming,Brooks, Harold B.
, p. 1943 - 1947 (2007/10/03)
Structure-based design approach was successfully used to guide the evolution of imidazopyridine scaffold yielding new structural class of highly selective inhibitors of cyclin dependent kinases that were able to form a new interaction with an identified residue of the protein, Lys89. Compounds from this series have shown no detectable effect when tested against a representative set of other serine/threonine kinases such as GSK3β, CAMKII, PKA, PKC-α,β,ε,γ. Compound 2i inhibits proliferation in HCT 116 cells in tissue culture. Synthesis, co-crystal structure of CDK2 in complex with compound 2i, and preliminary SAR study are disclosed.
Chemoselective arylsulfenylation of 2-aminoimidazo[1,2-α]pyridines by phenyliodine(III) bis(trifiuoroacetate) (PIFA)
Hamdouchi, Chafiq,Sanchez, Concha,Ezquerra, Jesus
, p. 867 - 872 (2007/10/03)
A series of 2-(trifluoroacetamido)imidazo[1,2-a]pyridines was prepared and treated with phenyliodine(III) bis(trifluoroacetate) (PIFA) in the presence of a variety of thiols leading chemoselectively to the corresponding 3-sulfides. Exposure of these adducts to silica gel in MeOH/CH2Cl2 provides a convenient method for the cleavage of the trifluoroacetamide group.
