21038-70-0Relevant academic research and scientific papers
Synthesis of hydantoins and dihydrouracils via thermally-promoted cyclization of ureidoacetamides
Hillier, Michael C.,Gong, Hai-Hua,Clyne, Dean S.,Babcock, Martin J.
, p. 9413 - 9420 (2015/03/05)
The synthesis of hydantoins and dihydrouracils from ureidoacetamides has been carried out at high temperature in glycol solvents. A series of substrates were prepared and examined to determine the effect of substrate structure, N-acyl substitution (X), and solvent on the course of the reaction. A dramatic effect was observed when using ureidoacetamides (e.g., X=N-methyl-N-phenyl), which led to higher yields, faster reaction times, and lower racemization of chiral substrates. The rate of racemization of a chiral hydantoin in the presence of dibenzylamine and N-methyl aniline has also been determined. The thermal cyclization methodology has been applied to the preparation of a complex hydantoin.
Synthesis and DNA-cleaving activity of lactenediynes conjugated with DNA-complexing moieties
Banfi, Luca,Basso, Andrea,Bevilacqua, Elisabetta,Gandolfo, Valentina,Giannini, Giuseppe,Guanti, Giuseppe,Musso, Loana,Paravidino, Monica,Riva, Renata
, p. 3501 - 3518 (2008/09/21)
Lactenediynes are compounds characterized by the fusion of a β-lactam with a cyclodeca-3-ene-1,5-diyne. In this work the most promising members of this family have been activated by attaching a carbalkoxy or a carbamoyl group to the azetidinone nitrogen, and conjugated to various DNA-complexing moieties, either acting by intercalation or through groove binding. These conjugated artificial enediynes have been demonstrated to possess in vitro ability to produce single and double strand cleavage of plasmid DNA. As potency and capacity to induce double cut, they rank among the best simple enediyne analogues ever prepared. A thorough investigation was carried out in order to develop the best suited linkers for assembling these conjugates.
