111183-45-0

Basic information

• Product Name: (2S)-2-({[(4-bromophenyl)amino]carbonyl}amino)-4-methylpentanoic acid
• Synonyms: (2S)-2-({[(4-bromophenyl)amino]carbonyl}amino)-4-methylpentanoic acid
• CAS NO: 111183-45-0
• Molecular Weight: 329.194
• Mol File: 111183-45-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S)-2-({[(4-bromophenyl)amino]carbonyl}amino)-4-methylpentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-({[(4-bromophenyl)amino]carbonyl}amino)-4-methylpentanoic acid(111183-45-0)
• EPA Substance Registry System: (2S)-2-({[(4-bromophenyl)amino]carbonyl}amino)-4-methylpentanoic acid(111183-45-0)

Safety Data

• Hazardous Substances Data: 111183-45-0(Hazardous Substances Data)

Upstream product

• 2493-02-9 4-bromophenyl isocyanate 
• 2748-02-9 L-leucine tert-butyl ester hydrochloride 
• 1431754-08-3 tert-butyl (2S)-2-({[(4-bromophenyl)amino]carbonyl}amino)-4-methylpentanoate 

Downstream Products

• 1469858-84-1 (2S)-2-({[(4-bromophenyl)amino]carbonyl}amino)-4-methyl-N-(1H-tetrazol-5-ylmethyl)pentanamide 
• 1469858-97-6 ethyl hydrogen ({[(2S)-2-({[(4-bromophenyl)amino]carbonyl}amino)-4-methyl pentanoyl]amino}methyl)phosphonate 
• 1469858-83-0 diethyl ({[(2S)-2-({[(4-bromophenyl)amino]carbonyl}amino)-4-methylpentanoyl]amino}methyl)phosphonate 

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.

(2-UREIDOACETAMIDO)ALKYL DERIVATIVES AS FORMYL PEPTIDE RECEPTOR 2 MODULATORS

The present invention relates to (2-ureidoacetamido)alkyl derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of the N-formyl peptide receptor 2.