2006
DOI: 10.1021/jm0509400
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Synthesis, Pharmacology, and Structure−Activity Relationships of Novel Imidazolones and Pyrrolones as Modulators of GABAAReceptors

Abstract: New series of imidazolones and pyrrolones were synthesized. The compounds were tested regarding their anxiolytic properties due to modulation of the GABAA receptor response. Several derivatives exhibit considerable pharmacological activity while lacking the typical side effects of benzodiazepine receptor agonists. 1-(4-chlorophenyl)-4-morpholin-1-yl-1,5-dihydro-imidazol-2-one (2) and 1-(4-chlorophenyl)-4-piperidin-1-yl-1,5-dihydro-imidazol-2-one (3) were protective in the pentylenetetrazole test in rats with o… Show more

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Cited by 41 publications
(18 citation statements)
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“…[10][11][12] The 3-isoxazolidone nucleus constitutes the basic skeleton of natural compounds such as the antibiotic, D-cycloserine, 13 the L-canavanine catabolite, 14 and a series of compounds that have been designed in medicinal chemistry as ligands for different receptors of the central nervous system. 15 The construction of isoxazoline and isoxazole rings by the 1,3-dipolar cycloaddition (13DC) of a nitrile oxide to an alkene or alkyne has proven to be extremely useful. [5][6][7][8][9]16 In continuation of our interest in the synthesis of heterocyclic compounds based on multicomponent reactions (MCRs), 17 we describe the synthesis of spiro 3-bromo-4,5-dihydroisoxazoles 7 in high yields via the two-component condensation reaction of 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones 3 and dibromoformaldoxime (6) in THF using KHCO 3 at room temperature (Scheme 1).…”
Section: Dibromoformaldoximementioning
confidence: 99%
“…[10][11][12] The 3-isoxazolidone nucleus constitutes the basic skeleton of natural compounds such as the antibiotic, D-cycloserine, 13 the L-canavanine catabolite, 14 and a series of compounds that have been designed in medicinal chemistry as ligands for different receptors of the central nervous system. 15 The construction of isoxazoline and isoxazole rings by the 1,3-dipolar cycloaddition (13DC) of a nitrile oxide to an alkene or alkyne has proven to be extremely useful. [5][6][7][8][9]16 In continuation of our interest in the synthesis of heterocyclic compounds based on multicomponent reactions (MCRs), 17 we describe the synthesis of spiro 3-bromo-4,5-dihydroisoxazoles 7 in high yields via the two-component condensation reaction of 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones 3 and dibromoformaldoxime (6) in THF using KHCO 3 at room temperature (Scheme 1).…”
Section: Dibromoformaldoximementioning
confidence: 99%
“…In addition to, single-use citric acid sachets have been used as an inducement to get heroin users to exchange their dirty needles for clean needles in an attempt to decrease the spread of HIV and hepatitis [3].Synthesis of the pyrrole rings has attracted great interests due to biological and pharmaceutical properties. They have been used as human cytomegalovirus( HCMV) protease [4], CD45 protein tyrosinphosphatase [5], anti-cancer [6], also, Thiomarinol A4 as antibiotic has pyrrole rings [7], many of number alkaloids with biological activities have pyrrole rings [8], and these rings have been used as UCS1025A [9], Oteromycin [10]. In addition, these rings have been used HIV integrase [11], and they have also herbicidal [12] activities.…”
Section: Introductionmentioning
confidence: 99%
“…The binding site of BZDs is located between α and γ subunits (Rudolph and Knoflach, 2011[16]; Alerno et. al., 2012[2]; Grunwald et al, 2006[8]).…”
Section: Introductionmentioning
confidence: 99%