89483-06-7

Basic information

• Product Name: BOC-L-CYCLOPROPYLALANINE-DCHA
• Synonyms: BOC-ALA(BETA-CYCLOPROPYL)-OH DICYCLOHEXYLAMMONIUM SALT;BOC-ALA(CPRO)-OH DCHA;BOC-ALA(CYCLOPROPYL)-OH DCHA;BOC-BETA-CYCLOPROPYL-L-ALANINE DCHA;BOC-BETA-CYCLOPROPYL-L-ALA-OH DCHA;BOC-BETA-CYCLOPROPYL-ALANINE DCHA;BOC-BETA-CYCLOPROPYL-ALA-OH DCHA;N-ALPHA-T-BUTOXYCARBONYL-3-CYCLOPROPYL-L-ALANINE DICYCLOHEXYLAMMONIUM SALT
• CAS NO: 89483-06-7
• Molecular Formula: C₁₁H₁₉NO₄
• Molecular Weight: 410.59
• Mol File: 89483-06-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 377.2±25.0 °C(Predicted)
• Appearance: /
• Density: 1.162±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 4.00±0.10(Predicted)
• CAS DataBase Reference: BOC-L-CYCLOPROPYLALANINE-DCHA(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-CYCLOPROPYLALANINE-DCHA(89483-06-7)
• EPA Substance Registry System: BOC-L-CYCLOPROPYLALANINE-DCHA(89483-06-7)

Safety Data

• Hazardous Substances Data: 89483-06-7(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 104347-84-4 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-cyclopropylpropanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 102735-53-5 (2S)-2-amino-3-cyclopropylpropanoic acid 

Downstream Products

• 905927-61-9 {2-[3-(2-tert-butoxycarbonylamino-3-cyclopropyl-propionylamino)-4-cyclopropyl-2-hydroxy-butyrylamino]-acetylamino}-phenyl-acetic acid tert-butyl ester 
• 905929-73-9 (S)-2-[((S)-2-Cyclohexyl-2-isobutoxycarbonylamino-acetyl)-methyl-amino]-3-cyclopropyl-propionic acid methyl ester 
• 881902-59-6 (S)-2-[((S)-2-Cyclohexyl-2-isobutoxycarbonylamino-acetyl)-methyl-amino]-3-cyclopropyl-propionic acid 
• 905927-58-4 (S)-[2-((S)-3-Amino-4-cyclopropyl-2-hydroxy-butyrylamino)-acetylamino]-phenyl-acetic acid tert-butyl ester 
• 881902-38-1 [2-(3-tert-butoxycarbonylamino-4-cyclopropyl-2-hydroxy-butyrylamino)-acetylamino]-phenyl-acetic acid tert-butyl ester 
• 881902-43-8 ((1S,2S)-1-Cyclohexyl-3-{3-[(S)-2-cyclopropyl-1-(methoxy-methyl-carbamoyl)-ethyl]-1-cyclopropylmethyl-ureido}-2-hydroxy-propyl)-carbamic acid tert-butyl ester 
• 905927-76-6 {(S)-2-Acetoxy-3-[3-((2S,3S)-3-amino-3-cyclohexyl-2-hydroxy-propyl)-3-cyclopropylmethyl-ureido]-4-cyclopropyl-butyrylamino}-acetic acid methyl ester 
• 905930-08-7 (4S,5S)-5-{3-[(S)-2-(Carboxymethyl-carbamoyl)-1-cyclopropylmethyl-2-hydroxy-ethyl]-1-cyclopropylmethyl-ureidomethyl}-4-cyclohexyl-2,2-dimethyl-oxazolidine-3-carboxylic acid isobutyl ester 
• 881902-44-9 {(S)-2-Acetoxy-3-[3-((2S,3S)-3-tert-butoxycarbonylamino-3-cyclohexyl-2-hydroxy-propyl)-3-cyclopropylmethyl-ureido]-4-cyclopropyl-butyrylamino}-acetic acid methyl ester 
• 905927-78-8 {(S)-2-Acetoxy-3-[3-((2S,3S)-3-cyclohexyl-2-hydroxy-3-isobutoxycarbonylamino-propyl)-3-cyclopropylmethyl-ureido]-4-cyclopropyl-butyrylamino}-acetic acid methyl ester 
• 881902-52-9 (S)-[2-(3-{(S)-2-[((S)-2-Cyclohexyl-2-isobutoxycarbonylamino-acetyl)-methyl-amino]-3-cyclopropyl-propionylamino}-4-cyclopropyl-2-oxo-butyrylamino)-acetylamino]-phenyl-acetic acid 
• 881902-46-1 (S)-(2-{3-[3-((S)-3-Cyclohexyl-3-isobutoxycarbonylamino-2-oxo-propyl)-3-cyclopropylmethyl-ureido]-4-cyclopropyl-2-oxo-butyrylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester 
• 905929-87-5 (S)-[2-(3-{(S)-2-[((S)-2-Cyclohexyl-2-isobutoxycarbonylamino-acetyl)-methyl-amino]-3-cyclopropyl-propionylamino}-4-cyclopropyl-2-oxo-butyrylamino)-acetylamino]-phenyl-acetic acid tert-butyl ester 
• 905928-76-9 (4S,5S)-5-{3-[2-({[((S)-tert-Butoxycarbonyl-phenyl-methyl)-carbamoyl]-methyl}-carbamoyl)-1-cyclopropylmethyl-2-oxo-ethyl]-1-cyclopropylmethyl-ureidomethyl}-4-cyclohexyl-2,2-dimethyl-oxazolidine-3-carboxylic acid isobutyl ester 

Relevant articles and documents

Synthesis and evaluation of novel cyclopentane urea FPR2 agonists and their potential application in the treatment of cardiovascular inflammation

The discovery of natural specialized pro-resolving mediators and their corresponding receptors, such as formyl peptide receptor 2 (FPR2), indicated that resolution of inflammation (RoI) is an active process which could be harnessed for innovative approaches to tame pathologies with underlying chronic inflammation. In this work, homology modelling, molecular docking and pharmacophore studies were deployed to assist the rationalization of the structure-activity relationships of known FPR2 agonists. The developed pharmacophore hypothesis was then used in parallel with the homology model for the design of novel ligand structures and in virtual screening. In the first round of optimization compound 8, with a cyclopentane core, was chosen as the most promising agonist (β-arrestin recruitment EC50 = 20 nM and calcium mobilization EC50 = 740 nM). In a human neutrophil static adhesion assay, compound 8 decreased the number of adherent neutrophils in a concentration dependent manner. Further investigation led to the more rigid cycloleucines (compound 22 and 24) with improved ADME profiles and maintaining FPR2 activity. Overall, we identified novel cyclopentane urea FPR2 agonists with promising ADMET profiles and the ability to suppress the inflammatory process by inhibiting the neutrophil adhesion cascade, which indicates their anti-inflammatory and pro-resolving properties.

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