184589-06-8Relevant academic research and scientific papers
Conformational Analysis and Absolute Configuration of Axially Chiral 1-Aryl and 1,3-Bisaryl-xanthines
Mancinelli, Michele,Perticarari, Sofia,Prati, Luca,Mazzanti, Andrea
, p. 6874 - 6885 (2017/07/17)
The xanthine scaffold is known to be the forefather of a class of biological active molecules. Xanthine is a planar framework in which an aryl substituent linked in the 1 or 3 position is driven out of the xanthine plane because of the steric hindrance exerted by the two carbonyls. This work analyses the stereodynamics of some 1-aryl and 1,3-bisaryl-xanthines and describes the steric requirements needed to produce stable heteroaromatic atropisomers or diastereoisomers, with one or two N-Csp2 stereogenic axes. The N-C racemization barrier was found to be bigger than 25 kcal/mol. The absolute configurations of the novel atropisomers has been assigned using TD-DFT simulation of ECD spectra.
Synthesis of novel galactopyranosyl-derived spiro barbiturates
Ingle,Gaidhane,Dutta,Naha,Sengupta
, p. 661 - 671 (2007/10/03)
Malonic acid undergoes condensation readily with ureas to yield barbituric acids 2, which on bromination give 5,5-dibromobarbituric acids 3. Reaction of α-D-galactose with these 5,5-dibromo barbituric acids afforded 2,3-α-D-galactopyrano-1,4-dioxo-7,9-diaza-spiro[4,5]deca-6,8,10-triones 4. The structures of the products have been assigned on the basis of 1H NMR, 13C NMR, FAB-MS, optical activity, and elemental analysis. The title compounds are found to have antibacterial and antifungal activities.
