864825-21-8

Basic information

• Product Name: (S)-benzyl 1-(4-phenyl-1H-iMidazol-2-yl)ethylcarbaMate
• Synonyms: (S)-benzyl 1-(4-phenyl-1H-iMidazol-2-yl)ethylcarbaMate;N-[(1S)-1-(5-Phenyl-1H-imidazol-2-yl)ethyl]carbamic acid phenylmethyl ester;Carbamic acid, [(1S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]-, phenylmethyl ester;benzyl (S)-(1-(4-phenyl-1H-imidazol-2-yl)ethyl)carbamate
• CAS NO: 864825-21-8
• Molecular Formula: C₁₉H₁₉N₃O₂
• Molecular Weight: 321.37306
• EINECS: -0
• Mol File: 864825-21-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-benzyl 1-(4-phenyl-1H-iMidazol-2-yl)ethylcarbaMate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-benzyl 1-(4-phenyl-1H-iMidazol-2-yl)ethylcarbaMate(864825-21-8)
• EPA Substance Registry System: (S)-benzyl 1-(4-phenyl-1H-iMidazol-2-yl)ethylcarbaMate(864825-21-8)

Safety Data

• Hazardous Substances Data: 864825-21-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Benzyl 1-(4-phenyl-1H-imidazol-2-yl)ethylcarbamate is used as an impurity in Eluxadoline, an orally-active drug for reducing symptoms of irritable bowel syndrome such as diarrhea and abdominal pain. Its presence in the drug may affect the efficacy and safety of the treatment.

Upstream product

• 864825-19-4 benzyl (S)-(1-oxo-1-((2-oxo-2-phenylethyl)amino)propan-2-yl)carbamate 
• 1142-20-7 N-Cbz-Ala 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 6530-41-2 N-benzyloxycarbonyl-L-alanate de benzoylmethyle 

Downstream Products

• 864825-23-0 [(S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]amine 
• 864825-27-4 (2-(4-hydroxy-2,6-dimethyl-phenyl)-1-{isopropyl-[1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-carbamoyl}-ethyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

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Uveal melanoma is the ocular malignancy and mainly driven by oncogenic mutations of Gαq/11 proteins. Previous targeted therapy for melanoma treatment was limited to specific downstream signaling pathway, and inhibiting the "molecular switches"G proteins for melanoma treatment therapy was rarely described. We herein report the discovery of imidazopiperazine derivatives as Gαq/11 protein inhibitors. The most promising compound GQ127 showed good efficacy and safety in inositol monophosphate (IP1) assay by directly inhibiting Gαq/11 proteins. GQ127 induced uveal melanoma cells apoptosis and displayed potent antitumor activities in uveal melanoma cells viability, migration, and invasion. The effects of GQ127 on Gαq/11 signaling pathway were confirmed by analyzing the downstream effectors yes-associated protein (YAP) and extracellular signal-regulated kinase (ERK). More importantly, GQ127 significantly suppressed UM xenograft growth in mouse model without severe toxicity at the testing dose. These findings provide a lead compound that directly targets the Gαq/11 proteins for uveal melanoma treatment.

Identification of a dual δ or antagonist/μ or agonist as a potential therapeutic for diarrhea-predominant Irritable Bowel Syndrome (IBS-d)

A small set of acyclic analogs 5 were prepared to explore their structure-activity relationships (SARs) relative to heterocyclic core, opioid receptor (OR) agonists 4. Compound 5l was found to have very favorable OR binding affinities at the δ and μ ORs (r Ki δ = 1.3 nM; r Ki μ = 0.9 nM; h Ki μ = 1.7 nM), with less affinity for the κ OR (gp Ki κ = 55 nM). The OR functional profile for 5l varied from the previously described dual δ/μ OR agonists 4, with 5l being a potent, mixed dual δ OR antagonist/μ OR agonist [δ IC50 = 89 nM (HVD); μ EC50 = 1 nM (GPI); κ EC50 = 1.6 μM (GPC)]. Compound 5l has progressed through a clinical Phase II Proof of Concept study on 800 patients suffering from diarrhea-predominant Irritable Bowel Syndrome (IBS-d). This Phase II study was recently completed successfully, with 5l demonstrating statistically significant efficacy over placebo.

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