3720-03-4Relevant academic research and scientific papers
Regioselective synthesis of 7,8-dihydroimidazo [5,1-c][1,2,4]triazine-3, 6(2H,4H)-dione derivatives: A new drug-like heterocyclic scaffold
Tzvetkov, Nikolay T.,Euler, Harald,Mueller, Christa E.
, p. 1584 - 1593 (2012/11/07)
Dihydroimidazo[5,1-c][1,2,4]triazine-3,6(2H,4H)-dione derivatives were prepared by successive N3- and N1-alkylation of hydantoins, followed by regioselective thionation and subsequent cyclization under mild conditions. In a final alkylation step a further substituent may be introduced. The synthetic strategy allows broad structural variation of this new drug-like heterobicyclic scaffold. In addition to extensive NMR and MS analyses, the structure of one derivative was confirmed by X-ray crystallography.
N-HYDROXYFORMAMIDE DERIVATIVES AS INHIBITORS OF MATRIX METALLOPROTEINASES
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, (2008/06/13)
Compounds having formula (I) are matrix metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.
REVERSE HYDROXAMATE INHIBITORS OF MATRIX METALLOPROTEINASES
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, (2008/06/13)
Compounds having the formula are matrix metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.
Reverse hydroxamate inhibitors of matrix metalloproteinases
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, (2008/06/13)
Compounds having the formula are matrix metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.
Ring-Transformation of Imidazolidine-2,4-diones ( = Hydantoins ) to 4H-Imidazoles in the Reaction with 3-(Dimethylamino)-2,2-dimethyl-2H-azirines
Schlaepfer-Daehler, Marlise,Mukherjee-Mueller, Gabriele,Heimgartner, Heinz
, p. 1251 - 1261 (2007/10/02)
At ca. 70 deg C, 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1) and 5,5-disubstituted hydantoins 4 in MeCN or i-PrOH give 2-(1-aminoalkyl)-5-(dimethylamino)-4,4-dimethyl-4H-imidazoles 5 in good yield (Scheme 2).These products are decarboxylated 1:1 adducts of 1 and 4.A reaction mechanism is suggested in analogy to the previously reported reactions of 1 and NH-acidic heterocycles containing the CO-NH-CO-NH moiety (Scheme 5).The formation of ureas 6 and 7 can be rationalized by trapping the intermediate isocyanate F by an amine.No reaction is observed between 1 and 1,5,5- or 3,5,5-trisubstituted hydantoins in refluxing MeCN or i-PrOH, but an N-isopropylation of 1,5,5-trimethylhydantoin (8b) occurs in the presence of morpholine (Scheme 3).The reaction of the bis(azirine)dibromozink complex 11 and hydantoines 4 in refluxing MeCN yields zink complexes 12 of the corresponding 2-(1-aminoalkyl)-4H-imidazoles 5 (Scheme 4).
