54467-96-8

Basic information

• Product Name: 1-Azido-3-iodobenzene solution
• Synonyms: 1-Azido-3-iodobenzene solution;3-Iodophenyl azide solution
• CAS NO: 54467-96-8
• Molecular Formula: C₆H₄IN₃
• Molecular Weight: 245.02053
• Mol File: 54467-96-8.mol

Chemical Properties

• Flash Point: -33℃
• Appearance: /
• Storage Temp.: ?20°C
• BRN: 1939329
• CAS DataBase Reference: 1-Azido-3-iodobenzene solution(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azido-3-iodobenzene solution(54467-96-8)
• EPA Substance Registry System: 1-Azido-3-iodobenzene solution(54467-96-8)

Safety Data

• Hazard Codes: F,T
• Statements: 11-38-48/23/24/25
• Safety Statements: 16
• RIDADR: UN 2398 3 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 54467-96-8(Hazardous Substances Data)

Upstream product

• 53694-87-4 1-azido-4-iodo-benzene 
• 540-37-4 p-aminoiodobenzene 
• 626-01-7 3-Iodoaniline 

Downstream Products

• 1403497-66-4 1-(azidomethyl)-3-fluorobenzene 
• 1403497-55-1 [3-(azidomethyl)phenyl](4-methoxyphenyl)iodonium tosylate 
• 1403497-49-3 3-azidophenyl(4’-methoxyphenyl)iodonium tosylate 
• 1809031-84-2 1-(3-iodophenyl)-4-(3-nitrophenyl)-1H-1,2,3-triazole 
• 1443134-68-6 3{1N-(3-iodophenyl)-1H-1,2,3-triazol-4yl}methyloxybetulinic acid 
• 1380433-16-8 (S)-N-(3-(3-azidophenyl)-2-phthalimidopropionyl)-2-methylthioaniline 
• 1262439-47-3 N-((1-(3-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(diethylamino)ethanamide 

Relevant articles and documents

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.

Structural and Activity Relationships of 6-Sulfonyl-8-Nitrobenzothiazinones as Antitubercular Agents

The benzothiazinone (BTZ) scaffold compound PBTZ169 kills Mycobacterium tuberculosis by inhibiting the essential flavoenzyme DprE1, consequently blocking the synthesis of the cell wall component arabinans. While extraordinarily potent against M. tuberculosis with a minimum inhibitory concentration (MIC) less than 0.2 ng/mL, its low aqueous solubility and bioavailability issues need to be addressed. Here, we designed and synthesized a series of 6-methanesulfonyl substituted BTZ analogues; further exploration introduced five-member aromatic heterocycles as linkers to attach an aryl group as the side chain. Our work led to the discovery of a number of BTZ derived compounds with potent antitubercular activity. The optimized compounds 6 and 38 exhibited MIC 47 and 30 nM, respectively. Compared to PBTZ169, both compounds displayed increased aqueous solubility and higher stability in human liver microsomes. This study suggested that an alternative side-chain modification strategy could be implemented to improve the druglike properties of the BTZ-based compounds.

Synthesis of Azidoanilines by the Buchwald-Hartwig Amination

We report a Buchwald-Hartwig amination compatible with azido functionality. Treatment of azidoaryl iodides and amines with fourth-generation Buchwald precatalyst coordinated by CPhos and sodium tert-butoxide in 1,4-dioxane at 50 °C afforded the corresponding azidoanilines while leaving the azido groups intact. The method showed a broad substrate scope and was applicable to the synthesis of diazido compounds as photoaffinity probe candidates of pharmaceutical amines and multiazido platform molecules.

A Comparative Assessment Study of Known Small-Molecule Keap1-Nrf2 Protein-Protein Interaction Inhibitors: Chemical Synthesis, Binding Properties, and Cellular Activity

Inhibiting the protein-protein interaction (PPI) between the transcription factor Nrf2 and its repressor protein Keap1 has emerged as a promising strategy to target oxidative stress in diseases, including central nervous system (CNS) disorders. Numerous non-covalent small-molecule Keap1-Nrf2 PPI inhibitors have been reported to date, but many feature suboptimal physicochemical properties for permeating the blood-brain barrier, while others contain problematic structural moieties. Here, we present the first side-by-side assessment of all reported Keap1-Nrf2 PPI inhibitor classes using fluorescence polarization, thermal shift assay, and surface plasmon resonance - and further evaluate the compounds in an NQO1 induction cell assay and in counter tests for nonspecific activities. Surprisingly, half of the compounds were inactive or deviated substantially from reported activities, while we confirm the cross-assay activities for others. Through this study, we have identified the most promising Keap1-Nrf2 inhibitors that can serve as pharmacological probes or starting points for developing CNS-active Keap1 inhibitors.

Inhibition of the FAD containing ER oxidoreductin 1 (Ero1) protein by EN-460 as a strategy for treatment of multiple myeloma

Multiple myeloma (MM) cells demonstrate high basal endoplasmic reticulum (ER) stress and are typically exquisitely sensitive to agents such as proteasome inhibitors that activate the unfolded protein response. The flavin adenosine dinucleotide (FAD) conta

Multifunctional Mono-Triazole Derivatives Inhibit Aβ42 Aggregation and Cu2+-Mediated Aβ42 Aggregation and Protect against Aβ42-Induced Cytotoxicity

Amyloid beta (Aβ) peptide aggregation is considered as one of the key hallmarks of Alzheimer's disease (AD). Moreover, Aβ peptide aggregation increases considerably in the presence of metal ions and triggers the generation of reactive oxygen species (ROS)

Design and synthesis of novel dehydroepiandrosterone analogues as potent antiproliferative agents

The aim of the present study was to determine the cytotoxic effects of a series of novel dehydroepiandrosterone derivatives containing triazole at the C16 position on human cancer cells. The cancer cells used in the present study were A549, Hel

Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents

Novel methodology for O-functionalization of carbohydrate derivatives has been established using bench-stable and easily prepared iodonium(III) reagents. Both electron-withdrawing and electron-donating aryl groups were introduced under ambient conditions and without precautions to exclude air or moisture. Furthermore, the approach was extended both to full arylation of cyclodextrin, and to trifluoroethylation of carbohydrate derivatives. This is the first general approach to introduce traditionally non-electrophilic groups into any of the OH groups around the sugar backbone. The methodology will be useful both in synthetic organic chemistry and biochemistry, as important functional groups can be incorporated under simple and robust reaction conditions in a fast and efficient manner.

Design, Synthesis, and Evaluation of Triazole Derivatives That Induce Nrf2 Dependent Gene Products and Inhibit the Keap1-Nrf2 Protein-Protein Interaction

The transcription factor Nrf2 regulates the expression of a large network of cytoprotective and metabolic enzymes and proteins. Compounds that directly and reversibly inhibit the interaction between Nrf2 and its main negative regulator Keap1 are potential pharmacological agents for a range of disease types including neurodegenerative conditions and cancer. We describe the development of a series of 1,4-diphenyl-1,2,3-triazole compounds that inhibit the Nrf2-Keap1 protein-protein interaction (PPI) in vitro and in live cells and up-regulate the expression of Nrf2-dependent gene products.

Synthesis of 3-O-propargylated betulinic acid and its 1,2,3-triazoles as potential apoptotic agents

Cytotoxic agents from nature are presently the mainstay of anticancer chemotherapy, and the need to reinforce the arsenal of anticancer agents is highly desired. Chemical transformation studies carried out on betulinic acid, through concise 1,2,3-triazole