53330-48-6Relevant articles and documents
Synthesis and structure–activity relationship of N-(piperidin-4-yl)benzamide derivatives as activators of hypoxia-inducible factor 1 pathways
Huang, Zhi-Ning,Liang, Han,Qiao, Hong,Wang, Bao-Rui,Qu, Ning,Li, Hua,Zhou, Run-Run,Wang, Li-Juan,Li, Shan-Hua,Li, Fu-Nan
, p. 1149 - 1161 (2018/07/21)
Guided by bioisosterism and pharmacokinetic parameters, we designed and synthesized a series of novel benzamide derivatives. Preliminary in vitro studies indicated that compounds 10b and 10j show significant inhibitory bioactivity in HepG2 cells (IC50 values of 0.12 and 0.13?μM, respectively). Compounds 10b and 10j induced the expression of HIF-1α protein and downstream target gene p21, and upregulated the expression of cleaved caspase-3 to promote tumor cells apoptosis.
Etherification of functionalized phenols with chloroheteroarenes at low palladium loading: Theoretical assessment of the role of triphosphane ligands in C-O reductive elimination
Platon, Melanie,Cui, Luchao,Mom, Sophal,Richard, Philippe,Saeys, Mark,Hierso, Jean-Cyrille
supporting information; experimental part, p. 3403 - 3414 (2012/02/02)
The present study highlights the potential of robust tridentate ferrocenylphosphanes with controlled conformation as catalytic auxiliaries in C-O bond formation reactions. Air-stable palladium triphosphane systems are efficient for selective heteroaryl ether synthesis by using as little as 0.2 mol% of catalyst. These findings represent an economically attractive and clean etherification of functionalized phenols, electron-rich, electron-poor and para-, meta- or ortho-substituted substrates, with heteroaryl chlorides, including pyridines, hydroxylated pyridine, pyrimidines and thiazole. The etherification tolerates very important functions in various positions, such as cyano, methoxy, amino, and fluoro groups, which is useful to synthesize bioactive molecules. DFT studies furthermore demonstrate that triphosphane ligands open up various new pathways for the C-O reductive elimination involving the third phosphane group. In particular, the rate for one of these new pathways is calculated to be about 1000 times faster than for reductive elimination from a complex with a similar ferrocenyl ligand, but without a phosphane group on the bottom Cp-ring. Coordination of the third phosphane group to the palladium(II) center is calculated to stabilize the transition state in this new pathway, thereby enhancing the reductive elimination rate. Copyright
