7269-04-7Relevant academic research and scientific papers
Flavin-cyclodextrin conjugates: Effect of the structure on the catalytic activity in enantioselective sulfoxidations
Hartman, Tomas,Herzig, Vladimir,Budesinsky, Milos,Jindrich, Jindrich,Cibulka, Radek,Kraus, Tomas
, p. 1571 - 1583 (2012)
A series of flavin-cyclodextrin conjugates has been prepared and tested in the enantioselective oxidations of prochiral aromatic and aliphatic sulfides with hydrogen peroxide. The newly prepared conjugates contain isoalloxazinium or alloxazinium moieties attached to the primary rim of α- and β-cyclodextrins at the C-6 positions. In addition, flavinium units were attached to the secondary rim of the β-cyclodextrin macrocycle. The relationship between the structural features and the catalytic performance of the conjugates, including those recently reported by us, was analyzed. The rate and enantioselectivity of the sulfoxidations catalyzed by flavin-cyclodextrin conjugates are influenced mainly by the size of the cyclodextrin cavity, the type of flavin unit (alloxazine or isoalloxazine), and by the relative orientation of the flavin and cyclodextrin moieties.
Fervenulin, 4-Deazafervenulin and 5-Deazaalloxazine Analogues. Synthesis and Antimicrobial Activity
Youssif, Shaker,Assy, Mohamed
, p. 2546 - 2559 (2007/10/03)
6-Chloro-1-methyluracil 1 was converted to 6-hydrazino- 2, and/or 6-arylamino-1-methyluracils 3a-d.Condensation of 2 with aldehydes led to the corresponding 6-hydrazones 4a-c.Cyclization of 2 with benzil provided 4-deaza-6-demethyl fervenulin 6.Refluxing 4a-c with NaNO2/AcOH afforded 4-deazafervenulins analogues 7a-c, the nitrosation of compound 2 provided 6-azido-1-methyluracil 8.The formylation of 3a-d by Vilsmeier reagent afforded 5-deazaalloxazines 10a-d.Reaction of 1 with cyanoacetic acid hydrazide led to the formation of 11. - Keywords: 6-chloro-1-methyluracil; 6-demethyl fervenulin; 5-deazaalloxazin
