143646-43-9

Basic information

• Product Name: Phenylalanine, N-acetyl-a-cyano-b-phenyl-, ethyl ester
• CAS NO: 143646-43-9
• Molecular Formula: C20H20N2O3
• Molecular Weight: 336.39
• Mol File: 143646-43-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Phenylalanine, N-acetyl-a-cyano-b-phenyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylalanine, N-acetyl-a-cyano-b-phenyl-, ethyl ester(143646-43-9)
• EPA Substance Registry System: Phenylalanine, N-acetyl-a-cyano-b-phenyl-, ethyl ester(143646-43-9)

Safety Data

• Hazardous Substances Data: 143646-43-9(Hazardous Substances Data)

Upstream product

• 90-99-3 diphenylchloromethane 
• 776-74-9 Bromodiphenylmethane 
• 90877-70-6 ethyl 2-acetamido-2-cyanoacetate 

Downstream Products

• 143647-12-5 (S)-1-((R)-2-Benzyloxycarbonylamino-3,3-diphenyl-propionyl)-pyrrolidine-2-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 143647-12-5 (S)-1-((S)-2-Benzyloxycarbonylamino-3,3-diphenyl-propionyl)-pyrrolidine-2-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 143218-11-5 Z-D-Dpa-Pro-OH 
• 143217-75-8 (S)-1-((R)-2-Amino-3,3-diphenyl-propionyl)-pyrrolidine-2-carboxylic acid [1-(3-guanidino-propyl)-2,5-dioxo-5-piperidin-1-yl-pentyl]-amide; compound with trifluoro-acetic acid 
• 143217-75-8 (S)-1-((S)-2-Amino-3,3-diphenyl-propionyl)-pyrrolidine-2-carboxylic acid [1-(3-guanidino-propyl)-2,5-dioxo-5-piperidin-1-yl-pentyl]-amide; compound with trifluoro-acetic acid 
• 143217-75-8 (S)-1-(2-Amino-3,3-diphenyl-propionyl)-pyrrolidine-2-carboxylic acid [1-(3-guanidino-propyl)-2,5-dioxo-5-piperidin-1-yl-pentyl]-amide; compound with trifluoro-acetic acid 
• 143217-99-6 C₅₂H₆₅N₇O₉S 
• 143217-99-6 C₅₂H₆₅N₇O₉S 
• 143217-93-0 C₄₈H₅₈N₆O₁₀S 
• 143217-93-0 C₄₈H₅₈N₆O₁₀S 
• 143217-83-8 C₄₄H₅₂N₆O₉S 
• 143217-82-7 C₄₄H₅₂N₆O₉S 
• 143218-00-2 C₄₉H₆₇N₇O₉S 
• 143218-23-9 C₄₄H₅₈N₆O₁₀S 

Relevant articles and documents

Synthesis and biological activity of ketomethylene pseudopeptide analogues as thrombin inhibitors

Ketomethylene pseudopeptide analogues Aa-Pro-Argψ(COCH2)Gly-pip, 1, where Aa are D- or L-amino acids (Dpa, β,β-diphenylalanine; αNal, α- naphthylalanine; βNal, β-naphthylalanine; Fgl, fluorenylglycine) with highly lipophilic side chains and ψ(COCH2) is a ketomethylene pseudopeptide bond, have been synthesized through a modified Dakin-West reaction under very mild conditions with a high yield using tripeptide 4 with a labile functional group directly on the side chain. Their enzymatic assay of thrombin inhibition has been carried out. The structure-activity relationship study indicated that a lipophilic side chain on the amino acid in the P3 position is very important for binding to the apolar site of thrombin. Compound 1a with D-Dpa at the P3 position has a K(i) of 0.2 μM and it doubles thrombin clotting time at only 3 times higher concentration. These values are about 7 times better than those of the corresponding D-Phe analogues. Furthermore, 1a shows poor inhibitory activity against plasmin, factor Xa, urokinase, and kallikrein. Preliminary in vivo testing (3-4-kg rabbit as the animal model) shows no observable side effect (change of blood pressure and accumulation of blood platelet in lungs) at a dose of 1 mg/kg.