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N-Boc-2-azidoethylamine, with the molecular formula C8H15N3O2, is a chemical compound derived from aminoethylamine. It features an azide functional group and a tert-butoxycarbonyl (Boc) protecting group on the nitrogen atom, which prevents unwanted reactions during chemical synthesis. N-Boc-2-azidoethylaMine serves as a versatile building block in the synthesis of pharmaceuticals, peptides, and complex molecules, and is also used in the creation of bioconjugates and for the labeling and modification of biomolecules through click chemistry reactions.

117861-38-8

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117861-38-8 Usage

Uses

Used in Organic Chemistry:
N-Boc-2-azidoethylamine is used as a building block for the synthesis of various pharmaceuticals and complex molecules, contributing to the development of new drugs and therapeutic agents.
Used in Peptide Synthesis:
N-Boc-2-azidoethylaMine is utilized in the synthesis of peptides, playing a crucial role in the formation of peptide bonds and the construction of peptide-based therapeutics.
Used in Bioconjugation:
N-Boc-2-azidoethylamine is employed as a linker in the formation of bioconjugates, enabling the attachment of biologically active molecules to other entities for various applications, such as drug delivery and imaging.
Used in Biomolecule Labeling and Modification:
N-Boc-2-azidoethylaMine serves as a tool for the labeling and modification of biomolecules, allowing researchers to study their structure, function, and interactions with other molecules.
Used in Click Chemistry Reactions:
Due to its azide functionality, N-Boc-2-azidoethylamine is often used in click chemistry reactions for the modification of biomolecules and materials, facilitating the rapid and efficient formation of new compounds and conjugates.

Check Digit Verification of cas no

The CAS Registry Mumber 117861-38-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,7,8,6 and 1 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 117861-38:
(8*1)+(7*1)+(6*7)+(5*8)+(4*6)+(3*1)+(2*3)+(1*8)=138
138 % 10 = 8
So 117861-38-8 is a valid CAS Registry Number.

117861-38-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-butyl N-(2-azidoethyl)carbamate

1.2 Other means of identification

Product number -
Other names N-Boc-2-Azidoethylamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:117861-38-8 SDS

117861-38-8Relevant articles and documents

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

Swider,Maslyk,Zapico,Coderch,Panchuk,Skorokhyd,Schnitzler,Niefind,De Pascual-Teresa,Ramos

, p. 72482 - 72494 (2015)

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.

Design and synthesis of dendrimers with facile surface group functionalization, and an evaluation of their bactericidal efficacy

Ladd, Elizabeth,Sheikhi, Amir,Li, Na,Van De Ven, Theo G.M.,Kakkar, Ashok

, (2017)

We report a versatile divergent methodology to construct dendrimers from a tetrafunctional core, utilizing the robust copper(I) catalyzed alkyne-azide cycloaddition (CuAAC, "click") reaction for both dendrimer synthesis and post-synthesis functionalization. Dendrimers of generations 1-3 with 8-32 protected or free OH and acetylene surface groups, were synthesized using building blocks that included acetylene- or azide-terminated molecules with carboxylic acid or diol end groups, respectively. The acetylene surface groups were subsequently used to covalently link cationic amino groups. A preliminary evaluation indicated that the generation one dendrimer with terminal NH3+ groups was the most effective bactericide, and it was more potent than several previously studied dendrimers. Our results suggest that size, functional end groups and hydrophilicity are important parameters to consider in designing efficient antimicrobial dendrimers.

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

Shyam, Radhe,Charbonnel, Nicolas,Job, Aurélie,Blavignac, Christelle,Forestier, Christiane,Taillefumier, Claude,Faure, Sophie

, p. 1513 - 1516 (2018)

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.

Labeling of Hyaluronic Acids with a Rhenium-tricarbonyl Tag and Percutaneous Penetration Studied by Multimodal Imaging

Henry, Lucas,Delsuc, Nicolas,Laugel, Cécile,Lambert, Fran?ois,Sandt, Christophe,Hostachy, Sarah,Bernard, Anne-Sophie,Bertrand, Hélène C.,Grimaud, Laurence,Baillet-Guffroy, Arlette,Policar, Clotilde

, p. 987 - 991 (2018)

Hyaluronic acids were labeled with a rhenium-tricarbonyl used as single core multimodal probe for imaging and their penetration into human skin biopsies was studied using IR microscopy and fluorescence imaging (labeled SCoMPI). The penetration was shown to be dependent on the molecular weight of the molecule and limited to the upper layer of the skin.

Novel JAK1-selective benzimidazole inhibitors with enhanced membrane permeability

Kim, Hyungmi,Kim, Mi Kyoung,Choo, Hyunah,Chong, Youhoon

, p. 3213 - 3215 (2016)

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).

Synthesis of a multibranched porphyrin-oligonucleotide scaffold for the construction of DNA-based nano-architectures

Clave, Guillaume,Chatelain, Gregory,Filoramo, Arianna,Gasparutto, Didier,Saint-Pierre, Christine,Le Cam, Eric,Pietrement, Olivier,Guerineau, Vincent,Campidelli, Stephane

, p. 2778 - 2783 (2014)

The interest in the functionalization of oligonucleotides with organic molecules has grown considerably over the last decade. In this work, we report on the synthesis and characterization of porphyrin-oligonucleotide hybrids containing one to four DNA str

Attractive Interactions between Heteroallenes and the Cucurbituril Portal

Reany, Ofer,Li, Amanda,Yefet, Maayan,Gilson, Michael K.,Keinan, Ehud

, p. 8138 - 8145 (2017)

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.

Synthesis and evaluation of 9-aminoacridines derived from benzyne click chemistry

Howell, Lesley A.,Howman, Aaron,O'Connell, Maria A.,Mueller, Anja,Searcey, Mark

, p. 5880 - 5883 (2009)

A small set of 9-aminoacridine-3- and 4-carboxamides were synthesized efficiently using the benzyne/azide click chemistry. The products bind to duplex DNA but have different antitumour activity in the HL60 cell line.

BETA-LACTAMASE INHIBITORS

-

Paragraph 0521, (2017/04/08)

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.

Synthesis and Evaluation of a Library of Trifunctional Scaffold-Derived Compounds as Modulators of the Insulin Receptor

Fabre, Benjamin,Pícha, Jan,Vaněk, Václav,Selicharová, Irena,Chrudinová, Martina,Collinsová, Michaela,?áková, Lenka,Budě?ínsky, Milo?,Jirá?ek, Ji?í

supporting information, p. 710 - 722 (2016/12/22)

We designed a combinatorial library of trifunctional scaffold-derived compounds, which were derivatized with 30 different in-house-made azides. The compounds were proposed to mimic insulin receptor (IR)-binding epitopes in the insulin molecule and bind to and activate this receptor. This work has enabled us to test our synthetic and biological methodology and to prove its robustness and reliability for the solid-phase synthesis and testing of combinatorial libraries of the trifunctional scaffold-derived compounds. Our effort resulted in the discovery of two compounds, which were able to weakly induce the autophosphorylation of IR and weakly bind to this receptor at a 0.1 mM concentration. Despite these modest biological results, which well document the well-known difficulty in modulating protein-protein interactions, this study represents a unique example of targeting the IR with a set of nonpeptide compounds that were specifically designed and synthesized for this purpose. We believe that this work can open new perspectives for the development of next-generation insulin mimetics based on the scaffold structure.

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