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Usage

InChI:InChI=1/C12H12N2O2/c15-10-12(9-6-7-9,14-11(16)13-10)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,13,14,15,16)

Upstream product

• 3481-02-5 cyclopropyl phenyl ketone 
• 151-50-8 potassium cyanide 
• 506-87-6 ammonium carbonate 

Downstream Products

• 1224939-48-3 3-(3-chloropropyl)-5-cyclopropyl-5-phenylimidazolidine-2,4-dione 
• 1338672-34-6 3-[(morpholin-4-yl)-methyl]-5-cyclopropyl-5-phenyl-imidazolidine-2,4-dione 
• 1338672-29-9 3-[(4-(2-methoxyethyl)piperazin-1-yl)methyl]-5-cyclopropyl-5-phenyl-imidazolidine-2,4-dione 
• 1338672-33-5 3-[(3,4-dihydro-1H-isoquinolin-2-yl)-methyl]-5-cyclopropyl-5-phenyl-imidazolidine-2,4-dione 
• 1338672-28-8 3-[(4-ethoxycarbonyl-piperazin-1-yl)-methyl]-5-cyclopropyl-5-phenyl-imidazolidine-2,4-dione 
• 1338672-23-3 3-[(4-phenethyl-piperazin-1-yl)-methyl]-5-cyclopropyl-5-phenyl-imidazolidine-2,4-dione 
• 1338672-27-7 3-[(4-benzyloxycarbonyl-piperazin-1-yl)-methyl]-5-cyclopropyl-5-phenyl-imidazolidine-2,4-dione 
• 1338672-25-5 3-[4-(1-phenylethyl)piperazin-1-ylmethyl]-5-cyclopropyl-5-phenyl-imidazolidine-2,4-dione 
• 1338672-26-6 3-[(4-benzoyl-piperazin-1-yl)-methyl]-5-cyclopropyl-5-phenyl-imidazolidine-2,4-dione 
• 1291067-01-0 (RS)-3-[(4-methyl-piperazin-1-yl)methyl]-5-cyclopropyl-5-phenylimidazolidine-2,4-dione 
• 1291067-03-2 (RS)-3-[(4-ethyl-piperazin-1-yl)methyl]-5-cyclopropyl-5-phenylimidazolidine-2,4-dione 
• 1291067-05-4 (RS)-3-[(4-(2-hydroxyethyl)piperazin-1-yl)methyl]-5-cyclopropyl-5-phenylimidazolidine-2,4-dione 
• 1291066-79-9 (RS)-3-[(4-benzylpiperazin-1-yl)methyl]-5-cyclopropyl-5-phenylimidazolidine-2,4-dione 
• 1291066-80-2 (RS)-3-[{4-(2,6-dichlorobenzyl)piperazin-1-yl}methyl]-5-cyclopropyl-5-phenylimidazolidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis and anticonvulsant activity of new N-Mannich bases derived from 5-cyclopropyl-5-phenyl-hydantoins

Synthesis, physicochemical and anticonvulsant properties of new N-Mannich bases 3-24 derived from 5-cyclopropyl-5-phenyl- and 5-cyclopropyl-5-(4- chlorophenyl)-hydantoins were described here. Initial anticonvulsant screening was performed using intraperitoneal (i.p.) maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) seizures tests. Selected derivatives were also screened in the 6-Hz test. The neurotoxicity was determined applying the rotorod test. The pharmacological results revealed that the majority of compounds were effective in MES and/or scPTZ tests. The quantitative studies after oral administration into rats showed that several molecules were more potent than phenytoin and ethosuximide which were used as reference antiepileptic drugs. From the whole series the most active was 3-[(4-phenylpiperazin-1-yl)-methyl]-5-cyclopropyl-5-phenyl-imidazolidine-2, 4-dione (3) with the ED50 value of 5.29 mg/kg in the MES test.

Synthesis and anticonvulsant activity of new N-Mannich bases derived from 5-cyclopropyl-5-phenyl- and 5-cyclopropyl-5-(4-chlorophenyl)-imidazolidine-2,4- diones

Synthesis, physicochemical and anticonvulsant properties of new N-Mannich bases derived from 5-cyclopropyl-5-phenyl- and 5-cyclopropyl-5-(4-chlorophenyl)- imidazolidine-2,4-diones have been described. Initial anticonvulsant screening was performed using intraperitoneal (ip.) maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) seizure tests. The neurotoxicity was determined applying the rotarod test. The in vivo results in mice showed that all compounds were effective especially in the MES screen. The quantitative evaluation after oral administration in rats showed that the most active was 5-cyclopropyl-5-phenyl-imidazolidine-2,4-dione (1) with ED50 values of 5.76 mg/kg (MES) and 57.31 mg/kg (scPTZ). This molecule was more potent than phenytoin and ethosuximide which were used as reference antiepileptic drugs. Additionally compound 1 with ED50 of 26.06 mg/kg in psychomotor seizure test (6-Hz) in mice showed comparable activity to new generation anticonvulsant - levetiracetam.

Synthesis and pharmacological evaluation of new 5-(cyclo)alkyl-5-phenyl- and 5-spiroimidazolidine-2,4-dione derivatives. Novel 5-HT1A receptor agonist with potential antidepressant and anxiolytic activity

The synthesis of 5-(cyclo)alkyl-5-phenyl- and 5-spiroimidazolidine-2,4-dione derivatives with an arylpiperazinylpropyl moiety (12-23) and their in vitro and in vivo pharmacological properties and molecular characteristics were described. The investigated compounds exhibited high affinity for 5-HT1A (13-22) and 5-HT2A (18, 20, 21, 23) receptors and diversified pharmacological profile. Compounds 17, 20 and 22 showed antagonistic, partial agonistic and agonistic activity, respectively, toward 5-HT1A receptor and they were investigated as potential antidepressants and/or anxiolytics. The most interesting compound 22 (1-[3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl]-3′,4′-dihydro-2′H-spiro[imidazolidine-4,1′-naphthalene]-2,5-dione), a pre- and postsynaptic 5-HT1A receptor agonist produced an antidepressant-like effect, which was more pronounced than that of imipramine in the forced swim test in mice, without affecting locomotor activity. Moreover, compound 22 produced a weak anxiolytic-like effect in the four-plate test in mice. Molecular docking studies of compound 22 to the homology model of the 5-HT1A receptor showed that a 3′,4′-dihydro-2′H-spiro[imidazolidine-4,1′-naphthalene]-2,5-dione moiety played an important role in stabilizing the ligand-receptor complex.