135884-98-9

Basic information

• Product Name: methyl 3-phenyl-3-(2'-oxo-3'-benzyl-1'-piperazinyl)propionate
• Synonyms: methyl 3-phenyl-3-(2'-oxo-3'-benzyl-1'-piperazinyl)propionate
• CAS NO: 135884-98-9
• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.43
• Mol File: 135884-98-9.mol

Chemical Properties

• Boiling Point: 543.2°Cat760mmHg
• Flash Point: 282.3°C
• Appearance: /
• Density: 1.17g/cm³
• CAS DataBase Reference: methyl 3-phenyl-3-(2'-oxo-3'-benzyl-1'-piperazinyl)propionate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-phenyl-3-(2'-oxo-3'-benzyl-1'-piperazinyl)propionate(135884-98-9)
• EPA Substance Registry System: methyl 3-phenyl-3-(2'-oxo-3'-benzyl-1'-piperazinyl)propionate(135884-98-9)

Safety Data

• Hazardous Substances Data: 135884-98-9(Hazardous Substances Data)

Upstream product

• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 203873-71-6 N-allyl-tert-butyloxycarbonyl-L-phenylalaninyl-L-phenylalanine methyl ester 
• 73270-67-4 (S)-2-allylamino-3-phenyl-propionic acid methyl ester 
• 133010-06-7 1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-phenylethyl)carbamate 
• 270257-61-9 (3S)-3-benzyl-4-tert-butyloxycarbonyl-5-hydroxy-1-(1'S-benzyl-1'-carbomethoxy)methyl-1,4-diaza-2-oxocyclohexane 
• 67-56-1 methanol 
• 119590-67-9 (2S,2'S)-2,2'-(ethane-1,2-diylbis(azanediyl))bis(3-phenylpropanoic acid) 

Downstream Products

• 212612-64-1 (3S)-3-benzyl-4-tert-butyloxycarbonyl-1-(1'S-benzyl-1'-carbomethoxy)methyl-1,4-diaza-2-oxocyclohexane 

Relevant articles and documents

New fMLF-OMe analogues containing constrained mimics of phenylalanine residue

In the context of a research program aimed at elucidating the HCO-Met- Leu-Phe-OMe (fMLF-OMe) structural features which control interactions with the receptor in correspondence with the C-terminal residue, four different analogues of the native ligand have been synthesized and evaluated. Compounds 1-3 possess the general formula HCO-Met-Leu-Xaa-OMe with Xaa = N- benzylglycine, N-benzylphenylalanine, and α,α-dibenzylglycine, respectively. In the analogue 4 the constraint at the C-terminus has been obtained by incorporating a 2-oxopiperazine ring, made up of two phenylalanine residues, to replace the native C-terminal Phe residue. The consequences of the chemical modifications on the activity of the new analogues are discussed.

Conformationally constrained substance P analogues: The total synthesis of a constrained peptidomimetic for the Phe7-Phe8 region

A lactam-based peptidomimetic for the Phe7-Phe8 region of substance P has been synthesized. The synthesis used an anodic amide oxidation to selectively functionalize the C5-position of a 3-pheylproline derivative. The resulting proline derivative was coupled to a Cbz-protected phenylalanine, and an intramolecular reductive amination strategy used to convert the coupled material into a bicyclic piperazinone ring skeleton. The net result was a dipeptide building block that imbedded one of two proposed receptor bound conformations for the Phe7-Phe8 region of substance P into a bicyclic ring skeleton. The building block was then converted into a constrained substance P analogue with the use of solid-phase peptide synthesis. A similar intramolecular reductive amination strategy was used to synthesize a substance P analogue having only Phe7 constrained, and the original 3-phenylproline was converted into a substance P analogue having only Phe8 constrained. All of the analogues were examined for their ability to displace substance P from its NK-1 receptor.

Conformational probes for elucidating the nature of substance P binding to the NK1 receptor: Initial efforts to map the Phe7-Phe8 region

Three substance P analogs with conformation constraints in the Phe7- Phe8 region have been prepared in connection with an effort to differentiate two families of potential conformations for the binding of substance P to its NK1