109573-05-9

Basic information

• Product Name: Carbamic acid, N-[2-(4-pyridinyl)ethyl]-, 1,1-dimethylethylester
• Synonyms: Carbamic acid, [2-(4-pyridinyl)ethyl]-, 1,1-dimethylethylester (9CI);4-[2-(N-(tert-Butoxycarbonyl)amino)ethyl]pyridine;tert-butyl 2-(pyridin-4-yl)ethylcarbamate
• CAS NO: 109573-05-9
• Molecular Formula: C12H18 N2 O2
• Molecular Weight: 222.287
• Mol File: 109573-05-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Carbamic acid, N-[2-(4-pyridinyl)ethyl]-, 1,1-dimethylethylester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, N-[2-(4-pyridinyl)ethyl]-, 1,1-dimethylethylester(109573-05-9)
• EPA Substance Registry System: Carbamic acid, N-[2-(4-pyridinyl)ethyl]-, 1,1-dimethylethylester(109573-05-9)

Safety Data

• Hazardous Substances Data: 109573-05-9(Hazardous Substances Data)

Upstream product

• 100-43-6 4-vinylpyridine 

Downstream Products

• 501377-02-2 N-[2-[2-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]ethyl]benzamide 
• 791563-61-6 2-(1-acetylpiperidin-4-yl)ethanamine 
• 885954-19-8 tert-butyl N-[2-(piperidin-2-yl)ethyl]carbamate 
• 901772-24-5 C₄₁H₅₃N₇O₁₀S 

Relevant articles and documents

Structure-based evolution of subtype-selective neurotensin receptor ligands

Subtype-selective agonists of the neurotensin receptor NTS2 represent a promising option for the treatment of neuropathic pain, as NTS2 is involved in the mediation of m-opioid-independent anti-nociceptive effects. Based on the crystal structure of the subtype NTS1 and previous structure-activity relationships (SARs) indicating a potential role for the sub-pocket around Tyr11 of NT(8-13) in subtype-specific ligand recognition, we have developed new NTS2-selective ligands. Starting from NT(8-13), we replaced the tyrosine unit by β2-amino acids (type 1), by heterocyclic tyrosine bioisosteres (type 2) and peptoid analogues (type 3). We were able to evolve an asymmetric synthesis of a 5-substituted azaindolylalanine and its application as a bioisostere of tyrosine capable of enhancing NTS2 selectivity. The S-configured test compound 2a, [(S)-3-(pyrazolo[1,5-α]pyridine-5-yl)-propionyl11]NT(8-13), exhibits substantial NTS2 affinity (4.8 nm) and has a nearly 30-fold NTS2 selectivity over NTS1. The (R)-epimer 2b showed lower NTS2 affinity but more than 600-fold selectivity over NTS1.

Secondary amides of sulfonylated 3-amidinophenylalanine. New potent and selective inhibitors of matriptase

Matriptase is an epithelium-derived type II transmembrane serine protease and has been implicated in the activation of substrates such as pro-HGF/SF and pro-uPA, which are likely involved in tumor progression and metastasis. Through screening, we have identified bis-basic secondary amides of sulfonylated 3-amidinophenylalanine as matriptase inhibitors. X-ray analyses of analogues 8 and 31 in complex with matriptase revealed that these inhibitors occupy, in addition to part of the previously described S4-binding site, the cleft formed by the molecular surface and the unique 60 loop of matriptase. Therefore, optimization of the inhibitors included the incorporation of appropriate sulfonyl substituents that could improve binding of these inhibitors into both characteristic matriptase subsites. The most potent derivatives inhibit matriptase highly selective with Ki values below 5 nM. Molecular modeling revealed that their improved affinity results from interaction with the S4 site of matriptase. Analogues 8 and 59 were studied in an orthotopic xenograft mouse model of prostate cancer. Compared to control, both inhibitors reduced tumor growth, as well as tumor dissemination.