143218-10-4

Basic information

• Product Name: Cbz-3-(2-Naphthyl)-D-alanine
• Synonyms: Z-D-ALA(2-NAPH)-OH;Z-D-ALA(2-NAPHTHYL)-OH;Z-D-2-NAL-OH;Z-3-(2-NAPHTHYL)-D-ALANINE;RARECHEM AL CF 0900;N-ALPHA-CARBOBENZOXY-3-(2-NAPHTHYL)-D-ALANINE;CBZ -D-2-NAPHTHYLALANINE;Z-3-(2-NAPHTHYL)-D-ALANINE 98+%
• CAS NO: 143218-10-4
• Molecular Formula: C₂₁H₁₉NO₄
• Molecular Weight: 349.38
• Product Categories: Unusual Amino Acids;Z-Amino acid series
• Mol File: 143218-10-4.mol

Chemical Properties

• Boiling Point: 591.4oC at 760 mmHg
• Flash Point: 311.5oC
• Appearance: /
• Density: 1.275g/cm3
• Vapor Pressure: 7.82E-15mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: 2-8°C
• PKA: 3.86±0.30(Predicted)
• BRN: 5829411
• CAS DataBase Reference: Cbz-3-(2-Naphthyl)-D-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: Cbz-3-(2-Naphthyl)-D-alanine(143218-10-4)
• EPA Substance Registry System: Cbz-3-(2-Naphthyl)-D-alanine(143218-10-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 143218-10-4(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C21H19NO4/c23-20(24)19(22-21(25)26-14-15-6-2-1-3-7-15)13-16-10-11-17-8-4-5-9-18(17)12-16/h1-12,19H,13-14H2,(H,22,25)(H,23,24)/t19-/m1/s1

Upstream product

• 76985-09-6 (R)-2-naphthylalanine 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 289050-79-9 CBZ-D-3-(2-naphthyl)alanyl-3-amino-2-hydroxypropyl-phthalimide 
• 143218-03-5 C₅₀H₆₃N₇O₉S 
• 143217-97-4 C₄₆H₅₆N₆O₁₀S 
• 143217-90-7 C₄₂H₅₀N₆O₉S 
• 143218-17-1 (S)-1-((R)-2-Benzyloxycarbonylamino-3-naphthalen-2-yl-propionyl)-pyrrolidine-2-carboxylic acid 
• 220977-91-3 S-37435 
• 289050-81-3 CBZ-D-3-(2-naphthyl)alanyl-3-amino-2-hydroxypropyl-carbamic acid t-butylester 

Relevant articles and documents

NOVEL AMIDE COMPOUND, AND Pin1 INHIBITOR, THERAPEUTIC AGENT FOR INFLAMMATORY DISEASES AND THERAPEUTIC AGENT FOR CANCER THAT USE THE SAME

An object of the invention is to develop a group of new compounds with inhibitory activity against the function of Pin1 as candidate compounds for drugs. The present invention provides compounds represented by the following Formula (I) or salts thereof, as well as Pin1 inhibitors, pharmaceutical compositions, therapeutic or prophylactic agents for inflammatory diseases, for cancer, and for obesity, which are each prepared using any of the above compounds or salts thereof.

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.