260783-12-8Relevant articles and documents
Enhanced selectivities for the hydroxyl-directed methanolysis of esters using the 2-acyl-4-aminopyridine class of acyl transfer catalysts: Ketones as binding sites
Sammakia, Tarek,Hurley, T. Brian
, p. 974 - 978 (2000)
In this paper we describe the preparation of a series of 2-acyl-4- aminopyridines, and their use as catalysts for the hydroxyl-directed methanolysis of α-hydroxy esters in preference to α-methoxy esters. Hydroxyl-direction with these catalysts, which contain ketones at the 2- position of the pyridine, is achieved by reversible addition of the alcohol of the hydroxy ester to the ketone to provide the corresponding hemiketal. Their activity is compared to that of the previously described catalyst 2- formyl-4-pyrrolidinopyridine (FPP), which contains an aldehyde at the 2- position of the pyridine. The catalysts which contain ketones at the 2- position range in reactivity from 10 times slower to slightly faster than FPP, and certain of these are much more selective for the methanolysis of hydroxy esters than FPP. This increase in selectivity is ascribed to a decrease in the rate of the nondirected methanolysis reaction with the ketone-derived catalysts. The evidence suggests that the nondirected reaction does not proceed by an intermolecular general base mechanism, but rather via a nucleophilic catalysis mechanism in which the hydroxyl group of the hemiacetal formed upon addition of methanol to the aldehyde of FPP acts as the nucleophile. Since the hydroxyl group derived from a hemiketal is more hindered and less nucleophilic than that derived from a hemiacetal, the nondirected reaction is much slower for the catalysts containing ketones as binding sites.
Discovery of novel picolinamide-based derivatives as novel VEGFR-2 kinase inhibitors: Synthesis,: in vitro biological evaluation and molecular docking
Sun, Wuji,Fang, Shubiao,Yan, Hong
, p. 1054 - 1058 (2018/06/27)
Vascular endothelial growth factor receptor-2 (VEGFR-2) plays a crucial role in tumor angiogenesis, and inhibition of the VEGFR-2 signaling pathway has emerged as an attractive target for cancer therapy. In our effort, a novel series of picolinamide-based derivatives were designed and synthesized as potent and effective VEGFR-2 inhibitors. All the newly prepared compounds were evaluated in vitro for their antiproliferative activity against A549 and HepG2 cell lines. Among the new compounds, 8j and 8l exhibited better activity against both A549 and HepG2 cell lines. Molecular docking was performed to investigate the binding capacity and binding mode with VEGFR-2 (PDB code: 4ASD).
Design, synthesis and antiproliferative activities of diaryl thiourea derivatives as anticancer agents
Yao, Jianwen,He, Zuopeng,Chen, Jing,Chen, Daquan,Sun, Wei,Xu, Wenfang
, p. 2423 - 2430,8 (2020/09/16)
Two new series of diaryl thiourea containing sorafenib derivatives 9a-9t were designed and synthesized, and their antiproliferative activities against PC-3, HCT116 and MDA-MB-231 cell lines were evaluated. All compounds generally showed antiproliferative activity to PC-3 cells, most of the analogs exhibited potent antiproliferative activity to HCT116 cells, and compounds 9e, 9f, 9o and 9p demonstrated inhibitory activities against all three cell lines. The structures of all the newly synthesized compounds were determined by 1H NMR, 13C NMR and HRMS. Two series of diaryl thiourea derivatives have been designed, prepared, and tested for cytotoxicity against human tumor cells PC-3, HCT116 and MDA-MB-231. The results showed that all compounds generally had antiproliferative activity against PC-3 cells, and some compounds demonstrated competitive antiproliferative activities to sorafenib. Copyright
