345948-97-2Relevant articles and documents
Convenient Michael addition/β-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources
Padilha, Gustavo,Birmann, Paloma T.,Domingues, Micaela,Kaufman, Teodoro S.,Savegnago, Lucielli,Silveira, Claudio C.
, p. 985 - 990 (2017/02/15)
A concise and efficient, two-step approach toward 4-organoselenyl coumarin derivatives from the easily available 4-hydroxycoumarins, is reported. The synthesis was based on conventional tosylation followed by a tandem selena-Michael addition/β-elimination reaction of an aryl-/benzyl-selenolate anion on the corresponding 4-tosyloxycoumarins. The selenolate anions were conveniently generated in situ by exposure of the corresponding diselenides to NaBH4. Selected compounds demonstrated to exhibit antioxidant properties in mice cortex and hippocampus.
Design, synthesis and characterization of a novel class of coumarin-based inhibitors of inducible nitric oxide synthase
Jackson, Sharon A.,Sahni, Sukhveen,Lee, Lan,Luo, Yongyi,Nieduzak, Thaddeus R.,Liang, Guyan,Chiang, Yulin,Collar, Nicola,Fink, David,He, Wei,Laoui, Abdelazize,Merrill, Jean,Boffey, Ray,Crackett, Peter,Rees, Bryan,Wong, Melanie,Guilloteau, Jean-Pierre,Mathieu, Magali,Rebello, Sam S.
, p. 2723 - 2739 (2007/10/03)
Inducible nitric oxide synthase (iNOS) has been implicated in various central and peripheral pathophysiological diseases. Our high throughput screening initially identified a weak inhibitor of iNOS, thiocoumarin 13. From this lead, a number of potent derivatives were prepared that demonstrate favorable potency, selectivity and kinetics. Compound 30 has an IC50 of 60 nM for mouse iNOS and 185-fold and 9-fold selectivity for bovine eNOS and rat nNOS, respectively. In cellular assays for iNOS, this compound has micromolar potency. Furthermore, two compounds (16 and 30) demonstrate a reasonable pharmacokinetic profile in rodents. The synthesis, SAR, and biological activity of this novel class of compounds is described.