42460-46-8

Upstream product

• 1709-44-0 m-aminobenzaldehyde 
• 696-41-3 m-iodobenzaldehyde 
• 89937-85-9 1-azido-3-hydroxymethylbenzene 
• 87199-16-4 3-Formylphenylboronic acid 
• 3132-99-8 m-bromobenzoic aldehyde 
• 99-61-6 3-nitro-benzaldehyde 
• 6952-67-6 2-(3-nitrophenyl)-1,3-dioxolane 
• 6398-87-4 3-aminobenzaldehyde ethylene acetal 
• 108-98-5 thiophenol 
• 728880-78-2 3-azido-thiobenzoic acid S-pent-4-ynyl ester 

Downstream Products

• 1073616-01-9 Zn(N₄C₂₀H₈(C₆H₃(C(CH₃)3)2)3C₆H₄C₂HN₃C₆H₄CHO) 
• 1397394-92-1 3-(4-phenyl-1H-1,2,3-triazol-1-yl)benzaldehyde 
• 1421345-19-8 C₁₆H₁₆N₄O₄ 
• 1558987-64-6 C₂₄H₂₄N₄O₄ 
• 1558987-36-2 C₂₃H₂₂N₄O₄ 
• 1400981-66-9 ethyl 4-(3-azidophenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 113962-87-1 (3-azidophenyl)diazomethane 
• 364038-63-1 2-(3-azidophenyl)-4,4,5,5-tetramethyl-2H-imidazoline-1-oxide-3-oxyl 
• 455884-48-7 3-azidobenzaldehyde tosylhydrazone 

Relevant academic research and scientific papers

Reliable and diverse synthesis of aryl azides through copper-catalyzed coupling of boronic acids or esters with TMSN3

(Figure Presented) Aryl azide formation: The copper-catalyzed coupling reaction of boronic esters and acids with TMSN3 have been presented as a highly efficient, simple, broadly applicable, and less hazardous methodology for the practi cal synthesis of aryl azides with structural diversity (see scheme).

COMPOUNS, COMPOSITIONS AND METHODS OF USE

Herein, compounds, compositions and methods for modulating inclusion formation and stress granules in cells related to the onset of neurodegenerative diseases, musculoskeletal diseases, cancer, ophthalmological diseases, and viral infections are described.

Unambiguous Identification of β-Tubulin as the Direct Cellular Target Responsible for the Cytotoxicity of Chalcone by Photoaffinity Labeling

Chalcone is a simple and potentially privileged structure in medicinal chemistry with a diverse repertoire of biological activities, among which cytotoxicity is of particular interest. The sharp structure–activity relationship (SAR) for chalcone's cytotoxicity suggests structure-specific target interactions. Despite the numerous putative targets proposed, evidence for direct target interactions in cells is unavailable. In this study, guided by the sharp cytotoxic SAR, we developed a cytotoxic chalcone-based photoaffinity labeling (PAL) probe, (E)-3-(3-azidophenyl)-1-[3,5-dimethoxy-4-(prop-2-yn-1-yloxy)phenyl]-2-methylprop-2-en-1-one (C95; IC50: 0.38±0.01 μm), along with two structurally similar non-cytotoxic probes. These probes were used to search for the direct cellular target responsible for chalcone's cytotoxicity through intact cell-based PAL experiments, in which β-tubulin was identified to specifically interact with the cytotoxic probe (i.e., C95) but not the non-cytotoxic probes. A set of phenotypical and biochemical assays further reinforced β-tubulin as the cytotoxic target of chalcones. Peptide mass quantitation by mass spectrometric analysis revealed one peptide potentially labeled by C95, providing information on chalcone's binding site on β-tubulin.

Copper Acetate Catalyzed Regio-selective Synthesis of Substituted 1,2,3-Triazoles: A Versatile Azide–Alk-ene Cycloaddition/Oxidation Approach

A copper acetate catalyzed oxidative cycloaddition reaction of benzyl and aryl azides with terminal and internal olefins that contain electron-withdrawing groups (COOR, CONH2, CN, CHO, COR) has been developed. The reaction employs air as the oxidant and does not require any base or additives to afford 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles in good to excellent yields with high regioselectivity.

Synthesis and biological evaluation of triazole-containing N-acyl homoserine lactones as quorum sensing modulators

Many bacterial species are capable of assessing their local population densities through a cell-cell signaling mechanism termed quorum sensing (QS). This intercellular communication process is mediated by small molecule or peptide ligands and their cognate protein receptors. Numerous pathogens use QS to initiate virulence once they achieve a threshold cell number on a host. Consequently, approaches to intercept QS have attracted considerable attention as potential anti-infective therapies. Our interest in the development of small molecule tools to modulate QS pathways motivated us to evaluate triazole-containing analogs of natural N-acyl l-homoserine lactone (AHL) signals as non-native QS agonists and antagonists in Gram-negative bacteria. We synthesized 72 triazole derivatives of five broad structure types in high yields and purities using efficient Cu(i)-catalyzed azide-alkyne couplings. These compounds were evaluated for their ability to activate or inhibit two QS receptors from two prevalent pathogens-LasR from Pseudomonas aeruginosa and AbaR from Acinetobacter baumannii-using bacterial reporter strains. Several triazole derivatives were identified that were capable of strongly modulating the activity of LasR and AbaR. These compounds represent a new and synthetically accessible class of AHL analogs, and could find utility as chemical tools to study QS and its role in bacterial virulence.

Recyclable clay supported Cu (II) catalyzed tandem one-pot synthesis of 1-aryl-1,2,3-triazoles

Montmorillonite KSF clay supported CuO nanoparticles efficiently catalyzes one-pot aromatic azidonation of aryl boronic acids followed by regioselective azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reaction producing corresponding 1-aryl-1,2,3-triazole derivatives at room temperature in excellent yields without use of any additives. Investigations on mechanism of CuAAC revealed that sodium azide, which is used as azidonating reagent in one-pot protocol reduces Cu(II) to click-active Cu(I). The catalytic efficiency of another Cu(II) source CuSO4 in combination with NaN3 for this one-pot CuAAC protocol, further supported our mechanism. This is the first report for use of Cu(II)/NaN3 catalytic system for CuAAC protocol. The clay-Cu(II) catalyst being ligand-free, leaching-free, easy to synthesize from inexpensive commercially available precursors, recyclable, and environmentally friendly will be highly useful for economical synthesis of 1,4-disubstituted 1,2,3-triazoles.

Triazole bridges as versatile linkers in electron donor-acceptor conjugates

Aromatic triazoles have been frequently used as π-conjugated linkers in intramolecular electron transfer processes. To gain a deeper understanding of the electron-mediating function of triazoles, we have synthesized a family of new triazole-based electron donor-acceptor conjugates. We have connected zinc(II)porphyrins and fullerenes through a central triazole moiety-(ZnP-Tri-C60)-each with a single change in their connection through the linker. An extensive photophysical and computational investigation reveals that the electron transfer dynamics-charge separation and charge recombination-in the different ZnP-Tri-C60 conjugates reflect a significant influence of the connectivity at the triazole linker. Except for the m4m-ZnP-Tri-C6017, the conjugates exhibit through-bond photoinduced electron transfer with varying rate constants. Since the through-bond distance is nearly the same for all the synthesized ZnP-Tri-C60 conjugates, the variation in charge separation and charge recombination dynamics is mainly associated with the electronic properties of the conjugates, including orbital energies, electron affinity, and the energies of the excited states. The changes of the electronic couplings are, in turn, a consequence of the different connectivity patterns at the triazole moieties.

Facile synthesis of peptide-porphyrin conjugates: Towards artificial catalase

A facile synthetic method for peptide-porphyrin conjugates containing four peptide units on one porphyrin was developed using chemoselective reactions. The key building blocks, 5,10,15,20-tetrakis(3-azidophenyl)porphyrin 1 and 5,10,15,20-tetrakis(5-azido-3-pyridyl)porphyrin 2, were efficiently synthesized and used as substrates for two well-known chemoselective reactions, traceless Staudinger ligation and copper-catalyzed azide alkyne cycloaddition (so-called click chemistry). Both reactions gave the desired compounds, and click chemistry was superior for our purpose. To confirm the value of the established methodology, nine peptide-porphyrin conjugates were synthesized, and their catalase- and peroxidase-like activity in water was evaluated. Our synthetic strategy is expected to be valuable for the preparation of artificial heme protein models.

First triazole-linked porphyrin-fullerene dyads

(Chemical Equation Presented)A general procedure for the synthesis of 1,2,3-triazole-linked porphyrin-fullerene dyads is described. Four of these compounds have been prepared and characterized.

Photolysis and oxidation of azidophenyl-substituted radicals: Delocalization in heteroatom-based radicals

2-(4-Azidophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1- oxyl (14), 2-(4-azidophenyl)benzimidazole-1-oxide-3-oxyl (16), 2-(4-azidophenyl)-1,2,6-triphenylverdazyl (19), 2-(3-azidophenyl)-4,4,5,5- tetramethyl-4,5-dihydro-1H-imidazole-3-oxid