190904-15-5

Basic information

• Product Name: Glycine, N-cyclopentyl-, Methyl ester
• Synonyms: Glycine, N-cyclopentyl-, Methyl ester
• CAS NO: 190904-15-5
• Molecular Formula: C₈H₁₅NO₂
• Molecular Weight: 157.2102
• Mol File: 190904-15-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Glycine, N-cyclopentyl-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Glycine, N-cyclopentyl-, Methyl ester(190904-15-5)
• EPA Substance Registry System: Glycine, N-cyclopentyl-, Methyl ester(190904-15-5)

Safety Data

• Hazardous Substances Data: 190904-15-5(Hazardous Substances Data)

Usage

Description

Glycine, N-cyclopentyl-, methyl ester is a chemical compound characterized by the molecular formula C7H13NO2. It represents a methyl ester derivative of N-cyclopentylglycine, which is an amino acid derivative. Glycine, N-cyclopentyl-, methyl ester holds promise as a therapeutic agent for the central nervous system and is widely utilized in organic synthesis for incorporating the N-cyclopentylglycine moiety into a variety of molecules. Additionally, it plays a role in research and pharmaceutical applications, particularly in the realm of drug discovery and development.

Uses

Used in Organic Synthesis:
Glycine, N-cyclopentyl-, methyl ester is used as a synthetic intermediate for introducing the N-cyclopentylglycine moiety into various organic molecules. This application is crucial for the development of new compounds with potential applications in different fields.
Used in Research and Pharmaceutical Applications:
In the research and pharmaceutical industry, Glycine, N-cyclopentyl-, methyl ester is used as a potential central nervous system therapeutic agent. Its role in drug discovery and development is significant, as it may contribute to the creation of novel treatments for neurological disorders and conditions.
Used in Drug Discovery:
Glycine, N-cyclopentyl-, methyl ester is employed in drug discovery processes to explore its potential as a lead compound for the development of new pharmaceuticals. Its unique structure and properties make it a valuable candidate for further investigation and optimization.
Used in Development of Central Nervous System Therapies:
Within the realm of central nervous system therapies, Glycine, N-cyclopentyl-, methyl ester is utilized for its potential to modulate neurotransmission and influence neuronal function. This application is vital for the advancement of treatments targeting neurological diseases and disorders.
Proper handling and storage of Glycine, N-cyclopentyl-, methyl ester are essential to ensure safety and prevent any adverse effects, highlighting the importance of adhering to established procedures in its use across various industries.

Upstream product

• 120-92-3 cyclopentanone 
• 616-34-2 methoxycarbonylmethylamine 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 96-32-2 bromoacetic acid methyl ester 
• 1003-03-8 Cyclopentamine 

Relevant articles and documents

Design, synthesis and biological evaluation of novel 4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridine derivatives as potential BRD4 inhibitors

Recently, diverse kinase inhibitors were reported having interaction with BRD4. It provided a strategy for developing a new structural framework for the next-generation BRD4-selective inhibitors. Starting from PLK1 kinase inhibitor BI-2536, we designed 18 compounds by modifying dihydropteridine core. Compound 23 showed potent BRD4 inhibitory activities with IC50 of 79 nM and no inhibitory activities for PLK1. Cell antiproliferation assay was performed and potent inhibitory activity against MV4;11 with IC50 of 1.53 μM. Cell apoptosis and western blotting indicated compound 23 induced apoptosis by down-regulating c-Myc. These novel selective BRD4 inhibitors provided new lead compounds for further drug development.

Designing Dual Inhibitors of Anaplastic Lymphoma Kinase (ALK) and Bromodomain-4 (BRD4) by Tuning Kinase Selectivity

Concomitant inhibition of anaplastic lymphoma kinase (ALK) and bromodomain-4 (BRD4) is a potential therapeutic strategy for targeting two key oncogenic drivers that co-segregate in a significant fraction of high-risk neuroblastoma patients, mutation of ALK and amplification of MYCN. Starting from known dual polo-like kinase (PLK)-1-BRD4 inhibitor BI-2536, we employed structure-based design to redesign this series toward compounds with a dual ALK-BRD4 profile. These efforts led to compound (R)-2-((2-ethoxy-4-(1-methylpiperidin-4-yl)phenyl)amino)-7-ethyl-5-methyl-8-((4-methylthiophen-2-yl)methyl)-7,8-dihydropteridin-6(5H)-one (16k) demonstrating improved ALK activity and significantly reduced PLK-1 activity, while maintaining BRD4 activity and overall kinome selectivity. We demonstrate the compounds' on-target engagement with ALK and BRD4 in cells as well as favorable broad kinase and bromodomain selectivity.

BRD4 Structure-Activity Relationships of Dual PLK1 Kinase/BRD4 Bromodomain Inhibitor BI-2536

A focused library of analogues of the dual PLK1 kinase/BRD4 bromodomain inhibitor BI-2536 was prepared and then analyzed for BRD4 and PLK1 inhibitory activities. Particularly, replacement of the cyclopentyl group with a 3-bromobenzyl moiety afforded the most potent BRD4 inhibitor of the series (39j) with a Ki = 8.7 nM, which was equipotent against PLK1. The superior affinity of 39j over the parental compound to BRD4 possibly derives from improved interactions with the WPF shelf. Meanwhile, substitution of the pyrimidine NH with an oxygen atom reversed the PLK1/BRD4 selectivity to convert BI-2536 into a BRD4-selective inhibitor, likely owing to the loss of a critical hydrogen bond in PLK1. We believe further fine-tuning will furnish a BRD4 "magic bullet" or an even more potent PLK1/BRD4 dual inhibitor toward the expansion and improved efficacy of the chemotherapy arsenal.