40856-75-5Relevant academic research and scientific papers
3, 5-disubstituted hydantoin compound as well as preparation method and application thereof
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Paragraph 0041; 0053; 0054; 0065; 0066, (2018/10/19)
The invention provides a 3, 5-disubstituted hydantoin compound as well as a preparation method and an application thereof. The structure of the compound is shown in formula I in the description. The application of the 3, 5-disubstituted hydantoin compound shown in the formula I or solvates, hydrates or salts of the compound in preparation of medicines for treating Alzheimer's disease, vascular dementia and other dementia diseases with memory impairment also belongs to the protection scope. Animal experiments prove that the compound has the effect of saving memory of animal models, has high safety, does not have mutagenicity, can stay in blood for several hours after oral administration and intravenous injection, and can enter the brain.
Dibromohydantoins as halogen bond (XB) donors: a route toward the introduction of chirality in halogen bonded systems
Nicolas, Irène,Jeannin, Olivier,Pichon, Delphine,Fourmigué, Marc
, p. 9325 - 9333 (2016/12/16)
N,N′-Dibromohydantoins, known as electrophilic bromination reagents, are successfully used here as halogen bond (XB) donors, as demonstrated in their crystalline adducts with para-substituted pyridines acting as halogen bond acceptors. 1:1 adducts of the achiral 5,5-dimethyl-N,N′-dibromohydantoin (DBH) are crystallized with methylisonicotinate, 4-trifluoromethylpyridine and 4-cyanopyridine, while both nitrogen atoms of pyrazine are engaged in halogen bonding in the 2:1 adduct (DBH)2·(pyrazine). A strengthening of the XB interaction between the imidic N-Br group of DBH and the pyridinic nitrogen atom is observed with the more electron rich pyridines in the order Py-CO2Me > Py-CF3 > Py-CN > pyrazine. Chiral hydantoins and their N,N′-dibromo derivatives are obtained in good yields from different amino acids (phenylglycine, phenylalanine, valine and leucine). The ability of such enantiopure N-iodoimide derivatives to act as halogen-bond donors is demonstrated in the 1:1 methylisonicotinate adduct with (S)-5-isobutyl-N,N′-dibromohydantoin.
Mechanochemical preparation of hydantoins from amino esters: Application to the synthesis of the antiepileptic drug phenytoin
Konnert, Laure,Reneaud, Benjamin,De Figueiredo, Renata Marcia,Campagne, Jean-Marc,Lamaty, Frdric,Martinez, Jean,Colacino, Evelina
, p. 10132 - 10142 (2015/02/19)
The eco-friendly preparation of 5- and 5,5-disubstituted hydantoins from various amino ester hydrochlorides and potassium cyanate in a planetary ball-mill is described. The one-pot/two-step protocol consisted in the formation of ureido ester intermediates, followed by a base-catalyzed cyclization to hydantoins. This easy-handling mechanochemical methodology was applied to a large variety of α- and β-amino esters, in smooth conditions, leading to hydantoins in good yields and with no need of purification steps. As an example, the methodology was applied to the "green" synthesis of the antiepileptic drug Phenytoin, with no use of any harmful organic solvent.
Dibutylphosphate (DBP) mediated synthesis of cyclic N,N′- disubstituted urea derivatives from amino esters: A comparative study
Agrawal, Sumit K.,Sathe, Manisha,Kaushik, M. P.,Halve, A. K.
supporting information, p. 5996 - 5999,4 (2020/08/20)
The N,N′-disubstituted urea derivatives such as amino acid hydantoins and dihydrouracil derivatives were prepared starting from natural and unnatural amino acid esters using dibutylphosphate (DBP). During the attempted synthesis of N-heterocycles with larger than six-membered rings containing the N,N′-disubstituted urea functionalities, three unexpected products namely squamolone, N-methyl pyrrolidine-2-one, and diketopiperazine were isolated.
