210686-21-8

Basic information

• Product Name: N-Boc-2-(7-Nitro-2,1,3-benzoxadiazol-4-ylaMino)ethylaMine
• Synonyms: N-Boc-2-(7-Nitro-2,1,3-benzoxadiazol-4-ylaMino)ethylaMine
• CAS NO: 210686-21-8
• Molecular Formula: C₁₃H₁₇N₅O₅
• Molecular Weight: 323.30458
• Mol File: 210686-21-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Boc-2-(7-Nitro-2,1,3-benzoxadiazol-4-ylaMino)ethylaMine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-2-(7-Nitro-2,1,3-benzoxadiazol-4-ylaMino)ethylaMine(210686-21-8)
• EPA Substance Registry System: N-Boc-2-(7-Nitro-2,1,3-benzoxadiazol-4-ylaMino)ethylaMine(210686-21-8)

Safety Data

• Hazardous Substances Data: 210686-21-8(Hazardous Substances Data)

Upstream product

• 10199-89-0 NBD chloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 57260-73-8 N-BOC-1,2-diaminoethane 

Relevant articles and documents

New fluorescent 2-phenylindolglyoxylamide derivatives as probes targeting the peripheral-type benzodiazepine receptor: Design, synthesis, and biological evaluation

Fluorescent ligands for the peripheral-type benzodiazepine receptor (PBR) featuring the 7-nitrobenz-2-oxa-1,3-diazol-4-yl moiety were synthesized, based on N,N-dialkyl-2-phenylindol-3-ylglyoxylamides, a potent, selective class of PBR ligands previously de

Fast diazaborine formation of semicarbazide enables facile labeling of bacterial pathogens

Bioorthogonal conjugation chemistry has enabled the development of tools for the interrogation of complex biological systems. Although a number of bioorthogonal reactions have been documented in literature, they are less ideal for one or several reasons including slow kinetics, low stability of the conjugated product, requirement of toxic catalysts, and side reactions with unintended biomolecules. Herein we report a fast (>103 M-1 s-1) and bioorthogonal conjugation reaction that joins semicarbazide to an aryl ketone or aldehyde with an ortho-boronic acid substituent. The boronic acid moiety greatly accelerates the initial formation of a semicarbazone conjugate, which rearranges into a stable diazaborine. The diazaborine formation can be performed in blood serum or cell lysates with minimal interference from biomolecules. We further demonstrate that application of this conjugation chemistry enables facile labeling of bacteria. A synthetic amino acid D-AB3, which presents a 2-acetylphenylboronic acid moiety as its side chain, was found to incorporate into several bacterial species through cell wall remodeling, with particularly high efficiency for Escherichia coli. Subsequent D-AB3 conjugation to a fluorophore-labeled semicarbazide allows robust detection of this bacterial pathogen in blood serum.

Sensitive Method for the Identification of Potential Sensitizing Impurities in Reaction Mixtures by Fluorescent Nitrobenzoxadiazole-Labeled Glutathione

Allergic contact dermatitis is a critical issue in the development of new chemicals. Minor impurities with strong skin-sensitizing properties can be generated as byproducts. However, it is very difficult to identify these skin sensitizers in product mixtures. In this study, fluorescent nitrobenzoxadiazole-labeled glutathione (NBD-GSH) was synthesized to identify small amounts of skin sensitizers in reaction mixtures. Twelve known skin sensitizers and three nonsensitizers were reacted with NBD-GSH. Adducts formed only with the skin sensitizers, which allowed for their detection by a fluorescence detector. Liquid chromatography-mass spectrometry (LC-MS) analyses showed that NBD-GSH reacted with the skin sensitizers via its thiol and amino groups. An adduct of NBD-GSH with the strong skin sensitizer 1-chloro-2,4-dinitrobenzene was detected with a limit of detection of 6 × 10-8 mol/L by high-performance liquid chromatography with fluorescence detection. When a reaction mixture from primary alcohol oxidation was incubated with NBD-GSH, a NBD-GSH adduct formed with skin-sensitizing aldehyde impurities and could be specifically detected by LC-MS with fluorescence detection. This method will be useful for detection and identification of small amounts of skin sensitizers in raw materials, intermediates, reaction mixtures, and end products in the chemical industry.

Engineering Boron Hot Spots for the Site-Selective Installation of Iminoboronates on Peptide Chains

Boronic acids (BAs) are a promising bioconjugation function to design dynamic materials as they can establish reversible covalent bonds with oxygen/nitrogen nucleophiles that respond to different pH, ROS, carbohydrates and glutathione levels. However, the dynamic nature of these bonds also limits the control over the stability and site-selectivity of the bioconjugation, which ultimately leads to heterogeneous conjugates with poor stability under physiological conditions. Here we disclose a new strategy to install BAs on peptide chains. In this study, a “boron hot spot“ based on the 3-hydroxyquinolin-2(1H)-one scaffold was developed and upon installation on a peptide N-terminal cysteine, enables the site-selective formation of iminoboronates with 2-formyl-phenyl boronic acids (Ka of 58128±2 m?1). The reaction is selective in the presence of competing lysine ?-amino groups, and the resulting iminoboronates, displayed improved stability in buffers solutions and a cleavable profile in the presence of glutathione. Once developed, the methodology was used to prepare cleavable fluorescent conjugates with a laminin fragment, which enabled the validation of the 67LR receptor as a target to deliver cargo to cancer HT29 cells.

Development and Characterization of a Fluorescent Probe for GLS1 and the Application for High-Throughput Screening of Allosteric Inhibitors

Glutaminase (GLS1) is a cancer energy metabolism protein which plays a predominant role in cell growth and proliferation. Because of its major involvement in malignant tumor, small-molecule GLS1 inhibitors are urgently needed to assess its therapeutic potential and for probing their underlying biology function. Recent studies showed that targeting the allosteric binding site represented a promising strategy for identifying potent and selective GLS1 inhibitors. Herein, we present the synthesis of two fluorescent probes targeting the allosteric binding site of GLS1 and their usage as mechanistic tools in multiple applicable assay platform. The fluorescence polarization (FP)-based binding assay enables easy, fast, and reliable screen of allosteric inhibitors from our in-house compound library obtained through click chemistry method. The obtained compound C147 (named as CPU-L1) has been proved to be more potent and with greater solubility than the control compound CB839, which could serve as promising leads for further optimization as novel GLS1 inhibitors.

Glutaminase micromolecular fluorescent probe and preparation method and application thereof

The invention discloses a glutaminase micromolecular fluorescent probe with a general formula (I) and a preparation method and application of the glutaminase micromolecular fluorescent probe. The structural module of the probe comprises a glutaminase binding group, a linker chain and a fluorescent reporter group. The glutaminase micromolecular fluorescent probe can be used for high-throughput screening of glutaminase inhibitors and guiding discovery and structure optimization of the glutaminase inhibitors. By using the probe with the structure as a tool molecule, the binding condition of a micromolecular compound and a target protein can be rapidly and accurately confirmed.

EASILY DECOMPOSABLE LIGNIN GENERATOR

PROBLEM TO BE SOLVED: To provide an easily decomposable lignin generator containing a compound that can be introduced to a structure of lignin and can make lignin easily decomposable. SOLUTION: The easily decomposable lignin generator contains a compound represented by general formula (1), where R1 to R3 are identical or different and each represent a hydrogen atom, alkoxy group or alkyl group, R4 represents an organic group, and n represents an integer from 0 to 3. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

LYSINE OLIGOMER DERIVATIVE AND CARTILAGE TISSUE MARKER MADE THEREOF

There is provided a lysine oligomer derivative, wherein an ε-amino group and a carboxyl group of lysines are linked via a peptide bond, and a group capable of generating or absorbing electromagnetic wave is bonded to a C-terminal carboxyl group, an N-terminal amino group and/or an α-amino group. This lysine oligomer derivative has the characteristic of specifically accumulating in the cartilage matrix and can generate or absorb an electromagnetic wave, and is, therefore, useful as a cartilage tissue marker.

A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides

d-Glucosamine derivatives bearing latent O4 functionality provide modified H/HS-type disaccharide donors for a final stage capping approach enabling introduction of conjugation-suitable, non-reducing terminal functionality to biologically important glycosaminoglycan oligosaccharides. Application to the synthesis of the first O4-terminus modified synthetic LMWH decasaccharide and an HS-like dodecasaccharide is reported.

Intracellular temperature sensing by a ratiometric fluorescent polymer thermometer

Intracellular temperature imaging could help to understand diverse biological reactions and functions in living cells. Herein, we report a nanothermometer based on ratiometric fluorescent polymers (RFPs) synthesized by the living/controlled reversible addition-fragmentation transfer polymerization method for intracellular temperature sensing. The thermometer was composed of a thermo sensitive polymer, a polarity sensitive fluorescent dye and a thermo insensitive fluorescent dye. With the increasing temperature, the fluorescent intensity of RFPs increased because of the fluorescent intensity enhancement of the polarity sensitive fluorescent dye induced by the self assembling of the thermo sensitive polymer. The prepared RFPs exhibited a fluorescence "turn-on" response at higher temperature. We further investigated the simultaneous temperature sensing and the ratiometric imaging of temperature variations associated with biological processes in living cells using this novel ratiometric probe. The polymer based ratiometric fluorescent thermometer can be used to precisely measure the temperature in living cells, and shows great potential in spatio-temporal temperature sensing down to the nanoscale within biological systems.