63999-80-4

Basic information

• Product Name: 3-Cyanophenylalanine
• Synonyms: H-M-CYANO-DL-PHE-OH;H-DL-PHE(3-CN)-OH;DL-3-CYANOPHENYLALANINE;2-AMINO-3-(3-CYANO-PHENYL)-PROPIONIC ACID;3-CYANO-DL-PHENYLALANINE;DL-3-CN-Phe-OH;3-Cyanophenylalanine;DL-3-cyanophenylalanine-HCl
• CAS NO: 63999-80-4
• Molecular Formula: C₁₀H₁₀N₂O₂
• Molecular Weight: 190.2
• Mol File: 63999-80-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 382.496 °C at 760 mmHg
• Flash Point: 185.127 °C
• Appearance: /
• Density: 1.282 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.14±0.10(Predicted)
• CAS DataBase Reference: 3-Cyanophenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyanophenylalanine(63999-80-4)
• EPA Substance Registry System: 3-Cyanophenylalanine(63999-80-4)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 63999-80-4(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white solid

InChI:InChI=1/C10H10N2O2/c11-6-8-3-1-2-7(4-8)5-9(12)10(13)14/h1-4,9H,5,12H2,(H,13,14)

Downstream Products

• 255375-04-3 3-(3-Cyano-phenyl)-2-(2,4,6-triisopropyl-benzenesulfonylamino)-propionic acid 
• 191872-32-9 2-{[(tert-butoxy)carbonyl]amino}-3-(3-cyanophenyl)propanoic acid 
• 1042927-00-3 3-brom phenyl sulfonyl-d/l-Phe(3-CN)-OH 
• 114579-89-4 3-(3-Carbamimidoyl-phenyl)-2-[2-(naphthalene-2-sulfonylamino)-acetylamino]-propionic acid phenethyl ester; compound with toluene-4-sulfonic acid 
• 114531-70-3 3-(3-Carbamimidoyl-phenyl)-2-[2-(naphthalene-2-sulfonylamino)-acetylamino]-propionic acid benzyl ester; compound with toluene-4-sulfonic acid 
• 114531-68-9 3-(3-Carbamimidoyl-phenyl)-2-[2-(naphthalene-2-sulfonylamino)-acetylamino]-propionic acid butyl ester; compound with toluene-4-sulfonic acid 
• 114531-72-5 3-(3-Carbamimidoyl-phenyl)-2-[2-(naphthalene-2-sulfonylamino)-acetylamino]-propionic acid isopropyl ester; compound with toluene-4-sulfonic acid 
• 114531-66-7 3-(3-Carbamimidoyl-phenyl)-2-[2-(naphthalene-2-sulfonylamino)-acetylamino]-propionic acid ethyl ester; compound with toluene-4-sulfonic acid 
• 114531-64-5 3-(3-Carbamimidoyl-phenyl)-2-[2-(naphthalene-2-sulfonylamino)-acetylamino]-propionic acid methyl ester; compound with toluene-4-sulfonic acid 
• 108998-47-6 3-(3-Methylsulfanylcarbonimidoyl-phenyl)-2-[2-(naphthalene-2-sulfonylamino)-acetylamino]-propionic acid; hydriodide 
• 108998-46-5 2-[2-(Naphthalene-2-sulfonylamino)-acetylamino]-3-(3-thiocarbamoyl-phenyl)-propionic acid 
• 114531-56-5 Nα-(2-Naphthylsulfonylglycyl)-3-amidinophenylalanin 

Relevant articles and documents

Synthesis and structure-activity relationships of potent thrombin inhibitors: Piperazides of 3-amidinophenylalanine

Thrombin is the key enzyme in the blood coagulation system, and inhibitors of its proteolytic activity are of therapeutic interest since they are potential anticoagulants. The most potent inhibitor of the benzamidine type is N(α)-[(2-naphthylsulfonyl)glycyl]-4-amidinophenylalanylpiperidide (NAPAP). However, NAPAP and other benzamidine derivatives do not show favorable pharmacological properties; above all, they have very low systemic bioavailability after oral administration. The goal of designing new compounds was to obtain potent inhibitors with improved pharmacokinetic properties. Piperazide derivatives of 3-amidinophenylalanine as the key building block were synthesized. The piperazine moiety opened the possibility to introduce quite different substituents on the second nitrogen using common synthetic procedures. Some of the newly synthesized compounds are potent inhibitors of thrombin and offer an approach to study structure-function relationships for inhibition of thrombin and related enzymes and for the improvement of their pharmacokinetic properties.