3363-68-6

Basic information

• Product Name: 2-Imidazolidinone, 1-methyl-3-phenyl-
• CAS NO: 3363-68-6
• Molecular Formula: C10H12N2O
• Molecular Weight: 176.218
• Mol File: 3363-68-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-Imidazolidinone, 1-methyl-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Imidazolidinone, 1-methyl-3-phenyl-(3363-68-6)
• EPA Substance Registry System: 2-Imidazolidinone, 1-methyl-3-phenyl-(3363-68-6)

Safety Data

• Hazardous Substances Data: 3363-68-6(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 7144-13-0 1-(2-chloroethyl)-3-phenylurea 
• 103-71-9 phenyl isocyanate 
• 36097-31-1 N-Methyl-N-<2-hydroxy-ethyl>-N'-phenyl-harnstoff 
• 1848-69-7 1-phenylimidazolidin-2-one 
• 74-88-4 methyl iodide 
• 1664-40-0 N-(2-aminoethyl)benzeneamine 

Downstream Products

• 1328951-98-9 2-tolyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328952-01-7 2-ethylphenyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328952-20-0 2,4-dimethylphenyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328952-17-5 2,4,5-trichlorophenyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328952-16-4 2,4,6-trichlorophenyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328951-99-0 3-tolyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328952-07-3 3-methoxyphenyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328952-08-4 3-fluorophenyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328952-18-6 3-nitrophenyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328952-13-1 3,4,5-trimethoxyphenyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328952-00-6 4-tolyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328953-30-5 4-methoxyphenyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328952-10-8 4-fluorophenyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1328952-09-5 4-chlorophenyl 4-(3-methyl-2-oxoimidazolidin-1-yl)benzenesulfonate 

Relevant articles and documents

Activation of Phenyl 4-(2-Oxo-3-Alkylimidazolidin-1-yl)benzenesulfonates Prodrugs by CYP1A1 as New Antimitotics Targeting Breast Cancer Cells

Prodrug-mediated utilization of the cytochrome P450 (CYP) 1A1 to obtain the selective release of potent anticancer products within cancer tissues is a promising approach in chemotherapy. We herein report the rationale, preparation, biological evaluation, and mechanism of action of phenyl 4-(2-oxo-3-Alkylimidazolidin-1-yl)benzenesulfonates (PAIB-SOs) that are antimicrotubule prodrugs activated by CYP1A1. Although PAIB-SOs are inert in most cells tested, they are highly cytocidal toward several human breast cancer cells, including hormone-independent and chemoresistant types. PAIB-SOs are N-dealkylated into cytotoxic phenyl 4-(2-oxo-3-imidazolidin-1-yl)benzenesulfonates (PIB-SOs) in CYP1A1-positive cancer cells, both in vitro and in vivo. In conclusion, PAIB-SOs are novel chemotherapeutic prodrugs with no equivalent among current antineoplastics and whose selective action toward breast cancer is tailored to the characteristic pattern of CYP1A1 expression observed in a large percentage of human breast tumors.

Lithiation of 1-arylimidazol-2(1H)-ones and 1-aryl-4,5-dihydroimidazol- 2(1H)-ones

1-Arylimidazol-2(1H)-ones are shown to be readily lithiated, using 2 mol equiv. of n-butyllithium, on the benzene ring, ortho to the heterocycle. 1-Aryl-4,5-dihydroimidazol-2(1H)-ones also undergo metalation on the aromatic substitutuent ortho to the heterocycle, but less efficiently. 1-Aryl-3-methylimidazol-2(1H)-ones are lithiated on the heterocyclic ring and then on the benzene ring ortho to the heterocycle. No ortho-directing effect was found for 1-aryl-4,5-dihydro-3-methylimidazol-2(1H)-ones.

Investigation of the Mitsunobu reaction of N-(2-hydroxyethyl)-N'- phenyl-ureas

The Mitsunobu reaction of N-(2-hydroxyethyl)-ureas 1 using PPh3 and EtO2CN=NCO2Et led to the mixture of N- and O-alkylation products or a single isomer depending on the substrates.