6427-66-3

Usage

Uses

Used in Photolysis Reactions:
4-Azidobenzoic acid is used as a photochemical agent for initiating photolysis reactions, where it can undergo decomposition upon exposure to light, facilitating various chemical transformations.
Used in Biomaterial Studies:
In the field of biomaterials, 4-Azidobenzoic acid is utilized as a chemical modifier to enhance the properties of materials, such as improving their biocompatibility or incorporating specific functional groups for targeted applications.
Used in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Reactions:
4-Azidobenzoic acid is employed as a reactant in copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, a widely used click chemistry technique for the formation of triazole rings. This reaction is valuable for the synthesis of various complex molecules and the modification of materials with high efficiency and selectivity.

InChI:InChI=1/C7H5N3O2/c8-10-9-6-3-1-5(2-4-6)7(11)12/h1-4,8H/p+1

Upstream product

• 7664-41-7 ammonia 
• 38556-93-3 4-azido-benzoic acid ethyl ester 
• 619-45-4 4-methoxycarbonyl aniline 
• 586-76-5 4-Bromobenzoic acid 
• 456-25-7 p-carboxyphenyl diazonium tetrafluoroborate 
• 150-13-0 4-amino-benzoic acid 
• 62-23-7 4-nitro-benzoic acid 
• 94-09-7 p-aminoethylbenzoate 
• 14047-29-1 4-carboxyphenylboronic acid 
• 122-04-3 4-nitro-benzoyl chloride 
• 76479-97-5 methyl 2,3-O-isopropylidene-5-O-(p-nitrobenzoyl)-β-D-ribofuranoside 
• 133463-51-1 (E)-3-(4-azidophenyl)acrylic acid 
• 555-06-6 sodium p-aminobenzoate 

Downstream Products

• 31641-62-0 4-triphenylphosphoranylidenamino-benzoic acid 
• 13452-14-7 2-methyl-6-benzoxazole carboxylic acid 
• 1026352-27-1 4-Azido-benzoic acid (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl ester 
• 194852-24-9 4-Azido-benzoic acid (1S,5R,6R)-6-hydroxy-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-8,10-dioxo-2-oxa-7,9-diaza-bicyclo[4.2.2]dec-5-yl ester 
• 586-91-4 azobenzene-4,4'-dicarboxylic acid 
• 150-13-0 4-amino-benzoic acid 
• 261911-92-6 5-O-(tert-butyldimethylsilyl)-13-O-[3-(4-azidobenzoylamino)propionyl]avermectin B_1a aglycone 
• 66493-39-8 4-(N-tert-butoxycarbonyl)aminobenzoic acid 
• 325708-72-3 2-(4-nitrophenyl)ethyl 6-{[(4-azidobenzoyl)oxy]methyl}-2-{[(dimethylamino)methylene]amino}-3,4,5,6,7,8-hexahydro-4-oxopteridine-5-carboxylate 
• 322405-76-5 4-azido-benzoic acid 2-benzyloxyacetyl-3,5-bis-(tert-butyl-diphenyl-silanyloxy)-phenyl ester 
• 402832-51-3 N-[2-(2,4-dichlorophenyl)ethyl]-4-azidophenylcarboxamide 
• 851869-38-0 Diphenyl-[4-(1H,1H,2H,2H-perfluorodecyl)phenyl]phosphine oxide 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel 4-substituted coumarin derivatives as antitumor agents

Herein, fifteen new compounds containing coumarin, 1,2,3-triazole and benzoyl-substituted arylamine moieties were designed, synthesized and tested in vitro for their anticancer activity. The results showed that all tested compounds had moderate antiproliferative activity against MDA-MB-231, a human breast cancer cell line, under both normoxic and hypoxic conditions. Furthermore, the 4-substituted coumarin linked with benzoyl 3,4-dimethoxyaniline through 1,2,3-triazole (compound 5e) displayed the most prominent antiproliferative activities with an IC50 value of 0.03 μM, about 5000 times stronger than 4-hydroxycoumarin (IC50 > 100 μM) and 20 times stronger than doxorubicin (IC50 = 0.60 μM). Meanwhile, almost all compounds revealed general enhancement of proliferation-inhibiting activity under hypoxia, contrasted with normoxia. A docking analysis showed that compound 5e had potential to inhibit carbonic anhydrase IX (CA IX).

Isolation of molybdenum(vi) from simulated leachates of irradiated uranium-aluminum targets using diluted and undiluted sulfate ionic liquids

A method is presented to separate molybdenum from other elements commonly present in oxidative alkaline leachates of irradiated uranium-aluminum targets for the production of molybdenum-99. The separation was accomplished by selective extraction of molybdate anions using triazolium and phosphonium sulfate ionic liquid extractants, either diluted in 1-octanol or undiluted. Molybdenum was then stripped from the organic phase using a sodium hydrogen carbonate solution. The extractant was regenerated by contacting the organic phase with an alkaline sulfate solution. The extraction mechanism and the influence of the diluent on the extractant performance were investigated. The reported method provides a promising alternative to state-of-the-art chromatographic processes, showing potential for limiting the production of radioactive waste.

Combinatorial synthesis of new fluorescent scaffolds using click chemistry

Azides and acetylenes are bio-orthogonal functional groups that can be readily coupled using copper(I)- or ruthenium(II)- catalyzed 1,3-dipolar cycloaddition reactions. Using non-fluorescent aromatic azides and aromatic acetylenes, covering a range of electron rich and poor building blocks, the Huisgen cycloaddition afford 1,4-disubstituted or 1,5-disubstituted 1,2,3-triazoles. Using a combinatorial approach by running reaction in parallel in polypropylene 96-well plates we discovered several new fluorescent 1,2,3-triazoles scaffolds. These compounds show diverse interactions with biomolecules that could find applications in biology in, for example, fluorescence microscopy or biomolecule quantification.

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Synthesis of Azaylide-Based Amphiphiles by the Staudinger Reaction

Catalyst- and reagent-free reactions are powerful tools creating various functional molecules and materials. However, such chemical bonds are usually hydrolysable or require specific functional groups, which limits their use in aqueous media. Herein, we report the development of new amphiphiles through the Staudinger reaction. Simple mixing of chlorinated aryl azide with a hydrophilic moiety and various triarylphosphines (PAr3) gave rise to azaylide-based amphiphiles NPAr3, rapidly and quantitatively. The obtained NPAr3 formed ca. 2 nm-sized spherical aggregates (NPAr3)n in water. The hydrolysis of NPAr3 was significantly suppressed as compared with those of non-chlorinated amphiphiles nNPAr3. Computational studies revealed that the stability is mainly governed by the decrease in LUMO around the phosphorus atom owing to the o-substituted halogen groups. Furthermore, hydrophobic dyes such as Nile red and BODIPY were encapsulated by the spherical aggregates (NPAr3)n in water.

Antiviral activity of 1,4-disubstituted-1,2,3-triazoles against HSV-1 in vitro

Background: Herpes simplex virus 1 (HSV-1) affects a large part of the adult population. Anti-HSV-1 drugs, such as acyclovir, target thymidine kinase and viral DNA polymerase. However, the emerging of resistance of HSV-1 alerts for the urgency in developing new antivirals with other therapeutic targets. Thus, this study evaluated a series of 1,4-disubstituted-1,2,3-triazole derivatives against HSV-1 acute infection and provided deeper insights into the possible mechanisms of action. Methods: Human fibroblast cells (HFL-1) were infected with HSV-1 17syn+ and treated with the triazole compounds at 50 mM for 24 h. The 50% effective drug concentration (EC50) was determined for the active compounds. Their cytotoxicity was also evaluated in HFL-1 with the 50% cytotoxic concentration (CC50) determined using CellTiter-Glo solution. The most promising compounds were evaluated by virucidal activity and influence on virus egress, DNA replication and transcription, and effect on an acyclovir-resistant HSV-1 strain. Results: Compounds 3 ((E)-4-methyl-N'-(2-(4(phenoxymethyl)-1H-1,2,3-triazol1yl)benzylidene)benzenesulfonohydrazide) and 4 (2,2'-(4,4'-((1,3-phenylen ebis(oxy))bis(methylene))bis(1H-1,2,3-triazole-4,1 diyl)) dibenzaldehyde) were the most promising, with an EC50 of 16 and 21 mM and CC50 of 285 and 2,593 mM, respectively. Compound 3 was able to inhibit acyclovir-resistant strain replication and to interfere with virus egress. Both compounds did not affect viral DNA replication, but inhibited significantly the expression of ICP0, ICP4 and gC. Compound 4 also affected the transcription of UL30 and ICP34.5. Conclusions: Our findings demonstrated that these compounds are promising antiviral candidates with different mechanisms of action from acyclovir and further studies are merited.

Benzimidazole–galactosides bind selectively to the Galectin-8 N-Terminal domain: Structure-based design and optimisation

We have obtained the X-ray crystal structure of the galectin-8 N-terminal domain (galectin-8N) with a previously reported quinoline–galactoside ligand at a resolution of 1.6 ?. Based on this X-ray structure, a collection of galactosides derivatised at O3 with triazole, benzimidazole, benzothiazole, and benzoxazole moieties were designed and synthesised. This led to the discovery of a 3-O-(N-methylbenzimidazolylmethyl)–galactoside with a Kd of 1.8 μM for galectin-8N, the most potent selective synthetic galectin-8N ligand to date. Molecular dynamics simulations showed that benzimidazole–galactoside derivatives bind the non-conserved amino acid Gln47, accounting for the higher selectivity for galectin-8N. Galectin-8 is a carbohydrate-binding protein that plays a key role in pathological lymphangiogenesis, modulation of the immune system, and autophagy. Thus, the benzimidazole-derivatised galactosides represent promising compounds for studies of the pathological implications of galectin-8, as well as a starting point for the development of anti-tumour and anti-inflammatory therapeutics targeting galectin-8.

Discovery of triazolyl thalidomide derivatives as anti-fibrosis agents

Fibrosis with excessive accumulation of extracellular matrix (ECM) often causes progressive organ dysfunction and results in many inflammatory and metabolic diseases, including systemic sclerosis, pulmonary fibrosis, advanced liver disease and advanced kidney disease. The store-operated calcium entry (SOCE) pathway and the related signaling pathway were both found to be the important routes for fibrogenesis. Our aim in this study was to discover novel compounds to inhibit fibrogenesis. A number of triazolyl thalidomide derivatives were synthesized and evaluated for their anti-fibrosis activities. Compounds 7b-e, 8c-d, 10a-b and 10e inhibited intracellular Ca2+ activation and showed no cytotoxicity. Among them, 6-{4-[(3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}hexanoic acid (10e) with the most potent inhibitory effect was chosen for further examination. The results revealed that compound 10e, a SOCE inhibitor, reversed the migratory ability of TGF-β1-induced myofibroblasts, dedifferentiated myofibroblasts to fibroblasts due to cytoskeleton remodeling, and restrained myofibroblast activation by targeting Orai1 and TGF-β1/SMAD2/3 signaling pathways. The in silico study indicated that compound 10e, with the appropriate lipophilic carbon chain and carboxylic acid, showed a good drug-likeness model score. Conclusively, the SOCE inhibitor, compound 10e, is used as a promising lead compound for the development of a new treatment for fibrosis. This journal is

Design, click conventional and microwave syntheses, DNA binding, docking and anticancer studies of benzotriazole-1,2,3-triazole molecular hybrids with different pharmacophores

Despite the availability of some drugs, there is an urgent need for effective anti-cancer medication. It is due to various side effects and non-functionality of the present drugs; especially at the late stage of cancer. Therefore, three series (4a-e, 6a-e and 8a-j; 21 compounds) of benzotriazole-1,2,3-triazole hybrids (carrying different pharmacophores) have been designed and synthesized (by both conventional and microwave syntheses) through the Cu(I)-catalyzed click 1,3-dipolar cycloaddition reaction of the propargylated benzotriazole with the appropriate aliphatic, aromatic and phenyl/benzyl acetamide azides. The syntheses times were from 6 to 12 h and 4 to 8 min in conventional and microwave syntheses. The yields were 80 to 86percent and 89 to 95percent in conventional and microwave syntheses; confirming microwave synthesis as an economic and eco-friendly method. These compounds were characterized by proper spectroscopic methods. The anticancer activities with A549 and H1299 lung cancer cell lines were in the range of 70.0 to 90.0percent for 4a-e series, 78.0 to 90.0percent for 6a-e series and 81.0 to 90.0percent for 8a-j series. The reported compounds showed good DNA binding constants in the range of 1.3 × 103 to 11.90 × 105 M?1. The docking results suggested strong DNA bindings of the reported compounds in the minor grooves of DNA; through hydrogen bonding and hydrophobic interactions. The quite good anticancer activities and high DNA binding constants have indicated that the reported molecules may be future anticancer agents.

Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids

To enhance the practicality of photouncaging system using 3-acyl-2-methoxyindolizines, direct acylation of indolizines with carboxylic acids was developed using condensation reagents, generally used for peptide coupling. This method allowed for caging a broad range of carboxylic acids with indolizines. The method enabled a facile synthesis of water-soluble caged bioactive carboxylic acids having an intramolecular photosensitizer. The efficient release of carboxylic acids from the synthesized caged compounds upon red light irradiation was confirmed in neutral buffered solutions.