75237-40-0Relevant academic research and scientific papers
A simple synthesis of 4-aroyl-5-methyl-1H-imidazol-2(3H)-one derivatives (Enoxymone analogues) from aryl methyl ketones via enaminones
Bezensek, Jure,Groselj, Uros,Stare, Katarina,Svete, Jurij,Stanovnik, Branko
, p. 294 - 307 (2014/03/21)
Aryl methyl ketones 1a-e gave with N,N-dimethylacetamide dimethylacetal (DMADMA) (E)-1- aryl-3-(dimethylamino)-but-2-en-1-ones 2a-e. Substitution of the N,N-(dimethylamino) group in the reaction with ammonium acetate afforded the corresponding (Z)-3-amino-1-aryl-but-2-en-1- ones 3a-e. In the reaction of 3a-e with diethyl azodicarboxylate intermediates 4a-e were formed, which were, in most cases without isolation, cyclized into ethyl (5-aroyl-4-methyl-2-oxo-2,3- dihydro-1H-imidazol-1-yl)carbamates 5a-e. Hydrolysis of the ester group, followed by the decarboxylation and deamination of intermediates 6a-c,e produced 4-aroyl-5-methyl-1Himidazol- 2(3H)-ones 7a-c,e.
4-(4-Guanidinobenzoyl)-2-imidazolones and related compounds: Phosphodiesterase inhibitors and novel cardiotonics with combined histamine H2 receptor agonist and PDE III inhibitor activity
Glass,Buschauer,Tenor,Bartel,Will-Shahab,Krause
, p. 709 - 719 (2007/10/03)
A series of new positive inotropic agents was synthesized with the aim of combining the pharmacophores of the imidazole-type phosphodiesterase (PDE) inhibitor enoximone and guanidine-type histamine H2 receptor agonists such as arpromidine. All compounds are para-substituted 4-benzoyl-5-alkyl-2-imidazolones. H2 agonism was incorporated by p-(hetero)alkyl substituents, in particular by an imidazolylpropyl guanidine group. In addition analogous ureas, cyanoguanidines carboxylate, and amines were prepared. These functional groups were either directly attached to the phenyl ring or linked by an appropriate spacer. The compounds were screened for positive inotropic activity in the isolated electrically stimulated guinea pig papillary muscle and for inhibition of PDE III (cGMP-inhibited cAMP PDE, isolated from guinea pig heart). The cardiotonics obtained proved to be either PDE III inhibitors, some of them surmounting up to 3-fold the potency of enoximone, or pharmacological hybrids combining both PDE III inhibitor and histamine H2 receptor agonist activities. These hybrids were the most potent positive inotropic substances at the papillary muscle, probably due to their synergistic mechanism of action. The participation of histamine H2 receptors could be demonstrated in the papillary muscle preparation by pretreatment with the H2 antagonist famotidine (10 μM) as well as by further pharmacological experiments using isolated perfused hearts of guinea pigs and rats, isolated guinea pig right atria, adenylyl cyclase and H2 receptor binding assay. At equieffective concentrations the moderate PDE III inhibitor and histamine H2 agonist N1-{4-[(1,3-dihydro-5-methyl-2-oxo-3H-imidazol-4-yl)-carbonyl]phenyl }-N2-[3-(1H-imidazol-4-yl)propyl]guanidine 65 and the 5-ethyl homologue 66 were about 2 and 10 times more potent than enoximone at the papillary muscle. Moreover, both compounds produced a 2.5-fold higher maximal response than the reference compound.
4-Aroylimidazol-2-ones and their use as pharmaceuticals
-
, (2008/06/13)
Novel 4-aroylimidazol-2-ones of the following general structure which are useful as antihypertensives, cardiotonics, antithrombotics, bronchodilators and uterospasmolytics STR1 wherein Ar is 2-furyl, 2-thienyl or phenyl, the latter of which may optionally
4-Aroyl-1,3-dihydro-2H-imidazol-2-ones, a new class of cardiotonic agents
Schnettler,Dage,Grisar
, p. 1477 - 1481 (2007/10/02)
A series of 4-aroyl-1,3-dihydro-2H-imidazol-2-ones was synthesized and evaluated for pharmacological activity in the anesthetized dog. Most members of this series produced dose-related increases in cardiac contractile force as well as relatively minor inc
