252665-94-4Relevant academic research and scientific papers
Glycosylated eumelanin building blocks by thioglycosylation of 5,6-diacetoxyindole with an expedient selenium-based dynamic-mixture methodology
Adinolfi, Matteo,D'Ischia, Marco,Iadonisi, Alfonso,Leone, Loredana,Pezzella, Alessandro,Valerio, Silvia
experimental part, p. 4333 - 4338 (2012/09/22)
A series of 3-thioglycosylated 5,6-diacetoxyindole derivatives, which are important tools for eumelanin research and application, were prepared through a practical and efficient approach exploiting a dynamic mixture of thioglycoside agents. The strategy is feasible for installing both mono- and disaccharide units and relies on the facile in situ conversion of glycosyl disulfides into the corresponding, more reactive, phenylselenenyl sulfides in the presence of diphenyl diselenide, N-bromosuccinimide (NBS) and tetrabutylammonium bromide (TBAB). An expedient thioglycosidation of 5,6-diacetoxyindole with a dynamic mixture of thioglycosides is described. Copyright
A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof
Adinolfi, Matteo,Capasso, Domenica,Di Gaetano, Sonia,Iadonisi, Alfonso,Leone, Loredana,Pastore, Antonello
, p. 6278 - 6283 (2011/10/10)
Symmetrical glycosyl disulfides can be prepared within a few hours from per-O-acetylated precursors via a sequential approach entailing short reactions and no purification of any intermediate. The final thiolate-to-disulfide oxidation step is noticeably accelerated by low amounts of phenyl diselenide under air. Applicability of the strategy to non-saccharidic symmetrical alkyl disulfides has also been examined. A preliminary assay of the cytotoxic activity of symmetrical 1,1′- disulfides was performed on two human tumor cell lines, and a noteworthy activity was recorded for a range of these synthetic compounds.
