131724-45-3

Basic information

• Product Name: (S)-N-Boc-4-Cyanophenylalanine
• Synonyms: BOC-L-PHE(4-CN);BOC-L-PHE(4-CN)-OH;BOC-P-CYANO-L-PHENYLALANINE;BOC-P-CYANO-L-PHE-OH;BOC-PHE(4-CN)-OH;BOC-PHE(P-CN)-OH;BOC-L-4-CYANOPHE;BOC-L-4-CYANOPHENYLALANINE
• CAS NO: 131724-45-3
• Molecular Formula: C₁₅H₁₈N₂O₄
• Molecular Weight: 290.31
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;a-amino
• Mol File: 131724-45-3.mol

Chemical Properties

• Melting Point: 152.3 °C
• Boiling Point: 432.4°C (rough estimate)
• Flash Point: 252.6 °C
• Appearance: White/Powder
• Density: 1.1611 (rough estimate)
• Vapor Pressure: 1.41E-10mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• Storage Temp.: -15°C
• PKA: 3.73±0.10(Predicted)
• BRN: 7715793
• CAS DataBase Reference: (S)-N-Boc-4-Cyanophenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-Boc-4-Cyanophenylalanine(131724-45-3)
• EPA Substance Registry System: (S)-N-Boc-4-Cyanophenylalanine(131724-45-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 131724-45-3(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white powder

InChI:InChI=1/C15H18N2O4/c1-15(2,3)21-14(20)17-12(13(18)19)8-10-4-6-11(9-16)7-5-10/h4-7,12H,8H2,1-3H3,(H,17,20)(H,18,19)/t12-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 718596-77-1 (S)-3-amino-3-(4-cyanophenyl)propanoic acid 
• 80852-36-4 4-Cyanphenylalaninhydrochlorid 
• 123-91-1 1,4-dioxane 
• 52117-01-8 N-acetyl-4-cyano-α-(ethoxycarbonyl)phenylalanine ethyl ester 
• 146664-08-6 N-acetyl-4-cyano-D,L-phenylalanine 
• 17201-43-3 4-cyanobenzyl bromide 
• 104-85-8 para-methylbenzonitrile 
• 167479-78-9 (S)-4-Cyanophenylalanine 

Downstream Products

• 228260-15-9 tert-butyl (S)-(3-(4-cyanophenyl)-1-(methylamino)-1-oxopropan-2-yl)carbamate 
• 190510-96-4 Naphthalene-2-sulfonic acid [(S)-2-azepan-1-yl-1-(4-cyano-benzyl)-2-oxo-ethyl]-amide 
• 207449-51-2 [(S)-2-(4-Aminomethyl-phenyl)-1-(cyclopentyl-methyl-carbamoyl)-ethyl]-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 207449-50-1 [(S)-2-(4-Cyano-phenyl)-1-(cyclopentyl-methyl-carbamoyl)-ethyl]-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 207449-48-7 (S)-3-(4-Aminomethyl-phenyl)-2-(2-trimethylsilanyl-ethoxycarbonylamino)-propionic acid methyl ester 

Relevant articles and documents

Peripheral Selective Oxadiazolylphenyl Alanine Derivatives as Tryptophan Hydroxylase 1 Inhibitors for Obesity and Fatty Liver Disease

Tryptophan hydroxylase 1 (TPH1) has been recently suggested as a promising therapeutic target for treating obesity and fatty liver disease. A new series of 1,2,4-oxadiazolylphenyl alanine derivatives were identified as TPH1 inhibitors. Among them, compound 23a was the most active in vitro, with an IC50 (half-maximal inhibitory concentration) value of 42 nM, showed good liver microsomal stability, and showed no significant inhibition of CYP and hERG. Compound 23a inhibited TPH1 in the peripheral tissue with limited BBB penetration. In high-fat diet-fed mice, 23a reduced body weight gain, body fat, and hepatic lipid accumulation. Also, 23a improved glucose intolerance and energy expenditure. Taken together, compound 23a shows promise as a therapeutic agent for the treatment of obesity and fatty liver diseases.

A new strategy for the development of highly potent and selective plasmin inhibitors

A new structure-based strategy for the design of potent and selective plasmin inhibitors was developed. These compounds could be prepared by cyclizations between the P3 and P2 amino acid residues of substrate-analogue inhibitors using metathesis or a copper-catalyzed azide alkyne cycloaddition in combination with standard peptide couplings. The most potent bis-triazole derivative 10 inhibits plasmin and plasma kallikrein with Ki of 0.77 and 2.4 nM, respectively, whereas it has poor activity against the related trypsin-like serine proteases thrombin, factor Xa, or activated protein C. Modeling experiments revealed that inhibitor 10 adopts a compact and rigid structure that fits well into the relatively open active site of plasmin and plasma kallikrein, while it is rejected from sterically demanding residues present in loops of the other enzymes. These results from modeling confirm the selectivity profile found for inhibitor 10 in enzyme kinetic studies. Such compounds might be useful lead structures for the development of new antifibrinolytic drugs for use in cardiac surgery with cardiopulmonary bypass or organ transplantations to reduce bleeding complications.

SERINE PROTEASE INHIBITORS

The invention provides methods of making and using compounds of the formula shown, which are inhibitors of human plasmin and plasma kallikrein. (Formula I) The compounds are useful for the prevention of blood loss, and as components of fibrin adhesives.

N-acylamino acid amide compounds and intermediates for preparation thereof

The present invention discloses the compound represented by the formula (I): wherein A represents the following formula (a-1) or the following formula (a-2): B represents the following formula (b): (wherein the symbols are each as defined in the specification) or a pharmaceutically acceptable salts thereof, and intermediates for the preparation thereof, which have excellent platelet aggregation inhibitory activity and other properties and useful as prophylactic or therapeutic agents for diseases associated with a fibrinogen receptor, thrombosis, infarction and the like.

Fluorobenzamidrazone thrombin inhibitors: Influence of fluorine on enhancing oral absorption

LB30057 (1) is a selective and efficacious oral thrombin inhibitor. Fluorine-substitution on the phenylene ring of the benzamidrazone portion in both compound 1 and its derivatives gave, in many cases, enhanced oral absorption in rats while maintaining the intrinsic potency and selectivity. Compound 2 demonstrated a 3-fold increase in absorption.

Rational design of selective thrombin inhibitors

Thrombin inhibitors with functionalized benzamidines as surrogates for arginine were designed, synthesized, and characterized. Amino acid sequence difference in the position 190 between thrombin and trypsin was exploited in the design to enhance selectivity over trypsin. A representative compound 6 showed high potency (Ki of 45.5 nM) and extremely high specificity over trypsin (over 10,000 fold).

Peptide compound and a process for the preparation thereof

The present invention concerns glycoprotein IIa/IIIb antagonists and platelet aggregation inhibitors of the formula (I): STR1 wherein R1 is aryl which may have one or more suitable substituent(s), R2 is carboxy(lower)alkyl or protect