20210-01-9Relevant academic research and scientific papers
Synthesis and reactivity of 5-methylenehydantoins
Fraile, José M.,Lafuente, Gustavo,Mayoral, José A.,Pallarés, Antonio
experimental part, p. 8639 - 8647 (2011/11/30)
5-Methylenehydantoin, as well as the N-mono- and N,N-di-protected derivatives, can be obtained by different synthetic routes. These compounds can undergo a large variety of reactions, such as Diels-Alder, epoxidation, methanol addition and conjugate addition reactions of different types of nucleophiles, including carbon (cyanide), nitrogen (piperidine) and sulfur (thiols, thioacetate) nucleophiles. The reactivity with electrophilic reagents, such as m-CPBA or methanol in acidic medium, and the need for Lewis acids to promote the conjugate addition reactions indicate that hydantoin is a poor electron-withdrawing group.
5,5-Disubstituted Hydantoins: Syntheses and Anti-HIV Activity
Comber, Robert N.,Reynolds, Robert C.,Friedrich, Joyce D.,Manguikian, Roupen A.,Buckheit, Robert W.,et al.
, p. 3567 - 3572 (2007/10/02)
A series of 5,5-disubstituted hydantoin derivatives was synthesized by alkylating 5,5-bis(mercaptomethyl)-2,4-imidazolidinedione (3) with various halomethylaromatic or halomethylheteroaromatic precursors, or by using the Buchener-Berg procedure on the required ketone.When evaluated for their ability to inhibit HIV-induced cell killing and virus production in CEM or MT-2 cells only compounds 2, 4n, 4o, and 4i demonstrated modest activity, the latter with an IC50 = 53 μM
