117861-38-8

Basic information

• Product Name: N-Boc-2-azidoethylaMine
• Synonyms: N-Boc-2-azidoethylaMine;tert-Butyl n-(2-azidoethyl)carbamate
• CAS NO: 117861-38-8
• Molecular Formula: C₇H₁₄N₄O₂
• Molecular Weight: 186.21166
• Mol File: 117861-38-8.mol
• Article Data: 38

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Boc-2-azidoethylaMine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-2-azidoethylaMine(117861-38-8)
• EPA Substance Registry System: N-Boc-2-azidoethylaMine(117861-38-8)

Safety Data

• Hazardous Substances Data: 117861-38-8(Hazardous Substances Data)

Usage

General Description

N-Boc-2-azidoethylamine is a chemical compound with the molecular formula C8H15N3O2. It is a derivative of aminoethylamine and contains an azide functional group. The "N-Boc" in its name refers to the presence of a tert-butoxycarbonyl (Boc) protecting group on the nitrogen atom, which helps to prevent undesired reactions with other functional groups during chemical synthesis. N-Boc-2-azidoethylaMine is commonly used in organic chemistry as a building block for the synthesis of various pharmaceuticals, peptides, and other complex molecules. It is also utilized in the development of bioconjugates and as a tool for the labeling and modification of biomolecules. Due to its azide functionality, N-Boc-2-azidoethylamine is often used in click chemistry reactions for the modification of biomolecules and materials.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 87156-40-9 1-amino-2-azidoethane 
• 58885-58-8 N-tert-butoxycarbonyl-3-aminopropanol 
• 158690-56-3 2-(tert-butoxycarbonylamino)ethyl-4-methylbenzenesulfonate 
• 26690-80-2 2-(N-tert-butoxycarbonylamino)ethanol 
• 1972-28-7 diethylazodicarboxylate 
• 39684-80-5 2-(tert-butoxycarbonylamino)ethyl bromide 
• 96628-67-0 2-(tert-butoxycarbonylamino)ethyl methanesulfonate 
• 57260-73-8 N-BOC-1,2-diaminoethane 

Downstream Products

• 1172596-96-1 methyl (S)-2-(3-(2-(tert-butoxycarbonyl)aminoethyl)thioureido)-3-phenylpropanoate 
• 1369825-28-4 C₃₆H₃₈N₄O₁₀ 
• 87156-40-9 1-amino-2-azidoethane 
• 1047626-95-8 N,N'-di-Boc-di-(azidoethyl)-p-xylylenediamine 
• 1195110-38-3 {2-[4-(4-{5-[5-(4-hydroxyphenyl)-3-phenyl-7H-pyrrol-2-ylimino]-4-phenyl-5H-pyrrol-2-yl}-phenoxymethyl)-[l,2,3]triazol-l-yl]ethyl}carbamic acid t-butyl ester, BF₂ chelate 

Relevant articles and documents

Synthesis, biological activity and structural study of new benzotriazole-based protein kinase CK2 inhibitors

A new series of 4,5,6,7-tetrabromobenzotriazole (TBB) derivatives was synthesized and characterized as CK2 inhibitors. They were readily synthesized using a click chemistry approach based on a Cu(i)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC). Some of the synthesized compounds present interesting inhibitory activities using an in vitro assay, with Ki values in the low micro molar range and a high degree of selectivity against a panel of 24 kinases. Selected compounds were tested for their antiproliferative effect on several cancer cell lines, and for their proapoptotic activity towards human Jurkat T-leukemia and MCF-7 breast adenocarcinoma cells, showing that they can be proposed as promising anticancer agents. Docking studies as well as crystallographic analysis allowed us to identify ligand-CK2 interactions that account for the molecular recognition process, and can help to further optimize this family of compounds as CK2 inhibitors.

1,2,3-Triazolium-Based Cationic Amphipathic Peptoid Oligomers Mimicking Antimicrobial Helical Peptides

Amphipathic cationic peptoids (N-substituted glycine oligomers) represent a promising class of antimicrobial peptide mimics. The aim of this study is to explore the potential of the triazolium group as a cationic moiety and helix inducer to develop potent antimicrobial helical peptoids. Herein we report the first solid-phase synthesis of peptoid oligomers incorporating 1,2,3-triazolium-type side chains and their evaluation against Escherichia coli, Enterococcus faecalis, and Staphylococcus aureus. Several triazolium-based oligomers, even of short length, selectively kill bacteria over mammalian cells. SEM visualization of S. aureus cells treated with a dodecamer and a hexamer reveals severe cell membrane damage and suggests that the longer oligomer acts by pore formation.

Novel JAK1-selective benzimidazole inhibitors with enhanced membrane permeability

The previously identified Janus kinase 1 (JAK1)-selective inhibitor, 1-(2-aminoethyl)-2-(piperidin-4-yl)-1H-benzo[d]imidazole-5-carboxamide (2), suffered from low cell permeability, which resulted in poor pharmacokinetic properties. In this study, by introducing less polar hydrogen bond donors at N1(a hydroxyalkyl or a methylaminoalkyl group) and C2 (a cyclohexanol group) positions, a series of novel benzimidazole derivatives were prepared, which exhibited selective JAK1 inhibitory activity (IC50against JAK1?=?0.08–0.15?μM; JAK1-selectivity?=?26–40 fold vs JAK2, 12–23 fold vs JAK3, and 38–54 fold vs Tyk2) along with significantly increased lipophilicity (3.3–15.8 times) as well as membrane permeability (6.3–12 times).

Attractive Interactions between Heteroallenes and the Cucurbituril Portal

In this paper, we report on the noteworthy attractive interaction between organic azides and the portal carbonyls of cucurbiturils. Five homologous bis-α,-azidoethylammonium alkanes were prepared, where the number of methylene groups between the ammonium groups ranges from 4 to 8. Their interactions with cucurbit[6]uril were studied by NMR spectroscopy, IR spectroscopy, X-ray crystallography, and computational methods. Remarkably, while the distance between the portal plane and most atoms at the guest end groups increases progressively with the molecular size, the β-nitrogen atoms maintain a constant distance from the portal plane in all homologues, pointing at a strong attractive interaction between the azide group and the portal. Both crystallography and NMR support a specific electrostatic interaction between the carbonyl and the azide β-nitrogen, which stabilizes the canonical resonance form with positive charge on the β-nitrogen and negative charge on the β;-nitrogen. Quantum computational analyses strongly support electrostatics, in the form of orthogonal dipole-dipole interaction, as the main driver for this attraction. The alternative mechanism of n a ?€? orbital delocalization does not seem to play a significant role in this interaction. The computational studies also indicate that the interaction is not limited to azides, but generalizes to other isoelectronic heteroallene functions, such as isocyanate and isothiocyanate. This essentially unexploited attractive interaction could be more broadly utilized as a tool not only in relation to cucurbituril chemistry, but also for the design of novel supramolecular architectures.

BETA-LACTAMASE INHIBITORS

Described herein are compounds and compositions that modulate the activity of beta -lactamases. In some embodiments, the compounds described herein inhibit beta-lactamase. In certain embodiments, the compounds described herein are useful in the treatment of bacterial infections.