1027167-32-3

Basic information

• Product Name: 1,1-dimethylethyl (2S)-trans-5-(<1,1'-biphenyl>-3-ylmethyl)-2-(1,1-dimethylethyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate
• CAS NO: 1027167-32-3
• Molecular Weight: 422.568
• Mol File: 1027167-32-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,1-dimethylethyl (2S)-trans-5-(<1,1'-biphenyl>-3-ylmethyl)-2-(1,1-dimethylethyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-dimethylethyl (2S)-trans-5-(<1,1'-biphenyl>-3-ylmethyl)-2-(1,1-dimethylethyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate(1027167-32-3)
• EPA Substance Registry System: 1,1-dimethylethyl (2S)-trans-5-(<1,1'-biphenyl>-3-ylmethyl)-2-(1,1-dimethylethyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate(1027167-32-3)

Safety Data

• Hazardous Substances Data: 1027167-32-3(Hazardous Substances Data)

Upstream product

• 14704-31-5 3-(bromomethyl)-1,1'-biphenyl 
• 119838-38-9 (2S)-1-(tert-butyloxycarbonyl)-2-tert-butyl-3-methylimidazolidin-4-one 
• 643-93-6 3-methylbiphenyl 

Downstream Products

• 164172-95-6 (S)-3-([1,1'-biphenyl]-3-yl)-2-aminopropanoic acid 

Relevant articles and documents

Potent, Orally Active, Competitive N-Methyl-D-aspartate (NMDA) Receptor Antagonists Are Substrates for a Neutral Amino Acid Uptake System in Chinese Hamster Ovary Cells

A series of enantiomerically pure (phosphonomethyl)-substituted phenylalanine derivatives related to SDZ EAB 515 (1) were prepared as competitive N-methyl-D-aspartate (NMDA) receptor antagonists.Unlike most known competitive NMDA antagonists, analogs in this series with the S-configuration are potent NMDA antagonists whereas analogs with the unnatural R-configuration are weak NMDA antagonists, as determined by receptor binding experiments and their anticonvulsant action in mice.Examination in a previously reported competitive NMDA pharmacophore model revealed that receptor affinity can be explained partially by a cavity that accommodates the biphenyl ring of 1, while the biphenyl ring of the R-enantiomer 2 extends into a disallowed steric region.We proposed that analogs with the natural S-configuration and a large hydrophobic moiety would have an advantage in vivo over analogs with an R-configuration by being able to use a neutral amino acid uptake system to enhance both peripheral adsorption and transport into the brain.Examination in a system L neutral amino acid transport carrier assay shows that 1 competes with L-Phe for transport in an apparent competitive and stereospecific manner (estimated Ki=50 μM).The 1- and 2-naphthyl derivatives 3a,3b were found to be among the most potent, competitive NMDA antagonists yet discovered, being ca. 15-fold more potent than 1 in vitro and in vivo, with a long duration of action.The title compound 3a had potent oral activity in MES (ED50=5.0 mg/kg). 3a also retains its ability to compete, albeit more weakly than 1 (estimated Ki=200 μM), for L-Phe uptake to CHO cells.In this series, analogs with the R-configuration are not substrates for the system L neutral amino acid transport carrier.These results provide evidence that central nervous system active agents can be designed as substrates of a neutral amino acid transporter as a means to enhance penetration of the blood-brain barrier.