6777-05-5Relevant academic research and scientific papers
Synthesis and evaluation of anti-inflammatory and antitussive activity of hydantion derivatives
Lu, Haibin,Kong, Dejuan,Wu, Bin,Wang, Shihan,Wang, Yongsheng
, p. 638 - 642 (2012/08/28)
1-Methylhydantion is a compound, which was isolated from Oviductus Ranae for the first time. In our study, we found that it showed good antitussive and anti-inflammatory activity. It is also the first report which illustrates the antitussive activity of hydantion derivative. A series of hydantion derivatives were synthesized and evaluated for their anti-inflammatory and antitussive activity in vivo. The pharmacological tests showed that compounds 7a, 7c and 7d have good anti-inflammatory and antitussive activity compared to Ibuprofen and codeine. Compound 7a in particular showed two-fold stronger anti-inflammatory activity than Ibuprofen.
Highly efficient dialkylphosphate-mediated syntheses of hydantoins and a bicyclohydantoin under solvent-free conditions
Kumar, Vinod,Rana, Hemlata,Sankolli, Ravish,Kaushik
experimental part, p. 6148 - 6151 (2011/11/30)
Diversely substituted hydantoins have been synthesized by new strategy from cyanamide based precursor, that is, methyl N-cyano-N-alkyl/arylaminoacetate. Dialkylphosphates were employed as the mild reagent to hydrolyze and cyclize the substrate in one step to give quantitative yields of the desired products. Syntheses of multivalent hydantoins viz bis-hydantoin, bicyclohydantoin have potentially widened the scope and applicability of the present method. Solvent-free conditions and very easy work-up procedure make the reaction convenient and eco-friendly. Single crystal structures of some of the representative compounds are also reported.
5-Benzylidene-hydantoins: Synthesis and antiproliferative activity on A549 lung cancer cell line
Zuliani, Valentina,Carmi, Caterina,Rivara, Mirko,Fantini, Marco,Lodola, Alessio,Vacondio, Federica,Bordi, Fabrizio,Plazzi, Pier Vincenzo,Cavazzoni, Andrea,Galetti, Maricla,Alfieri, Roberta R.,Petronini, Pier Giorgio,Mor, Marco
experimental part, p. 3471 - 3479 (2009/12/24)
Benzylidene hydantoins have been recently reported as a new class of EGFR inhibitors. We describe here a simple and efficient methodology for the parallel solution-phase synthesis of a library of 5-benzylidene hydantoins, which were evaluated for antiproliferative activity on the human lung adenocarcinoma A549 cell line. Various substituents at positions 1, 3 and 5 on the hydantoin nucleus were examined. In the presence of a 5-benzylidene group and of a lipophilic substituent at position 1, most of the tested compounds inhibited cell proliferation at a concentration of 20 μM. Compound 7 (UPR1024), bearing 1-phenethyl and (E)-5-p-OH-benzylidene substituents, was found to be the most active derivative of the series. It inhibited EGFR autophosphorylation and induced DNA damage in A549 cells. Compound 7 and other synthesized 5-benzylidene hydantoin derivatives increased p53 levels, suggesting that the dual mechanism of action was a common feature shared by compound 7 and other member of the series.
An efficient approach for the synthesis of N-1 substituted hydantoins
Kumar, Vinod,Kaushik,Mazumdar, Avik
scheme or table, p. 1910 - 1916 (2009/04/04)
An efficient three-step route for the synthesis of N-1 alkyl/aryl- substituted hydantoins was developed from inexpensive commercially available substrates. The reaction of amines with cyanogen bromide takes place to give monoalkyl/aryl cyanamides. This on treatment with methyl bromoacetate in the presence of sodium hydride in tetrahydrofuran affords methyl N-cyano-N-alkyl/arylaminoacetate, which undergoes hydrolysis and cyclization in the presence of 50% H2SO4 to afford N-1 substituted hydantoins in very good-to-excellent yields. Wide varieties of final products having primary, secondary, tertiary, and aryl substituents at the N-1 position were successfully synthesized by this method. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Process for producing 1-substituted-hydantoins
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, (2008/06/13)
The subject is to provides a process for producing 1-substituted-hydantoins of Formula I: STR1 wherein R1 represents d hydrocarbon group which may be substituted and others, cheracterized by reacting N-sustituted-N-alkcycarbonylamnilo-acetonitrile of Formula II: STR2 wherein R2 represents an alkyl group and others, with an alkali metal hydroxides or the like and then treating with an acid.
Process for producing 1-substituted-hydantoins
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, (2008/06/13)
The subject is to provides a process for producing 1-substituted-hydantoins of Formula I: wherein R1represents a hydrocarbon group which may be substituted and others,characterized by reacting N-substituted-N-alkoxycarbonylamino-acetonitrile of Formula II: wherein R2represents an alkyl group and others,with an alkali metal hydroxides or the like and then treating with an acid.
Derivatives of 5-[[1-(4'-carboxybenzyl)imidazolyl]methylidene]hydantoins as orally active angiotensin II receptor antagonists
Edmunds,Klutchko,Hamby,Bunker,Connolly,Winters,Quin III,Sircar,Hodges,Panek,Keiser,Doherty
, p. 3759 - 3771 (2007/10/03)
A series of 5-[[1-(4'-carboxybenzyl)imidazolyl]methylidene]hydantoins have been prepared and evaluated as in vitro and in vivo angiotensin II (Aug II) antagonists. Variation of substituents on the hydantoin ring leads to potent and selective Aug II antagonists with nanomolar IC50 values at the AT1 receptor and negligible affinity for the AT2 receptor. Preferred substituents include an n-butyl at R1 and an alkyl or heteroarylmethyl substituent at R2. The selection of the R2 substituent was guided in part by the calculation of its log P since a significant correlation was observed between CLOGP and AT2 binding affinity. The biphenyl tetrazole pharmacophore, common to a number of AT1 antagonists, could be replaced by, for example, a 4-carbomethoxyphenyl substituent resulting in potent Aug II antagonists both in vitro and in vivo. A representative compound of this series is 57, which reduced the mean arterial blood pressure of renal hypertensive rats by 40% at 30 mg/kg po and by 25% at 10 mg/kg po. In addition this compound was efficacious in the salt-deplete normotensive monkey model maximally decreasing blood pressure 27% at 10 mg/kg po. In summary, these compounds belong to a novel class of Aug II antagonists that lack the biphenyl tetrazole moiety yet display appreciable and long lasting oral activity.
SUBSTITUTED-5-METHYLIDENE HYDANTOINS WITH AT1 RECEPTOR ANTAGONIST PROPERTIES
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, (2008/06/13)
Substituted 1-benzylimidazole-5-methylidene hydantoins are disclosed as well as methods of preparing them, pharmaceutical compositions containing them, and method of using them. Intermediates useful in the preparation of the compounds of the invention are also disclosed and synthetic methods for preparing the novel intermediates. The compounds are useful as antagonists of angiotensin II and thus are useful in the control of hypertension, hyperaldosteronism, congestive heart failure, surgically induced vascular smooth muscle proliferation, and glaucoma.
