159979-97-2

Usage

Uses

Used in Organic Synthesis:
3-fluorobenzyl azide is used as a reagent in organic synthesis for its ability to participate in copper-catalyzed azide-alkyne cycloaddition reactions, leading to the formation of triazoles. These triazoles are significant in the pharmaceutical and materials industries due to their unique properties and potential applications.
Used in Bioconjugation:
In the field of bioconjugation, 3-fluorobenzyl azide is employed as a building block for the creation of bioconjugates. The click chemistry reactions involving 3-fluorobenzyl azide allow for the efficient and selective attachment of biomolecules, such as proteins, peptides, and nucleic acids, to various scaffolds and surfaces.
Used in Materials Science:
3-fluorobenzyl azide is utilized in materials science for the development of new materials with specific properties. The triazoles formed through its reactions contribute to the creation of advanced materials with applications in various industries, including electronics, coatings, and pharmaceuticals.
Used in Drug Development:
3-fluorobenzyl azide is an important tool in the pharmaceutical industry for the development of new drugs. Its ability to undergo efficient and selective chemical reactions enables the synthesis of novel drug candidates with potential therapeutic applications.

InChI:InChI=1/C7H6FN3/c8-7-3-1-2-6(4-7)5-10-11-9/h1-4H,5H2

Upstream product

• 456-41-7 1-(Bromomethyl)-3-fluorobenzene 
• 352-70-5 m-Fluorotoluene 
• 456-42-8 m-fluorobenzyl chloride 
• 4648-54-8 trimethylsilylazide 
• 456-48-4 3-Fluorobenzaldehyde 
• 456-47-3 3-fluoro-benzenemethanol 
• 446-48-0 o-fluorobenzyl bromide 

Downstream Products

• 1093975-82-6 1-(3-fluorobenzyl)-4-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1H-1,2,3-triazole 
• 1295479-53-6 C₂₅H₂₈F₃N₇O 
• 1360180-54-6 N-(3-((1-(3-fluorobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-phenyl)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide 

Relevant academic research and scientific papers

Synthesis, Docking, and Biological activities of novel Metacetamol embedded [1,2,3]-triazole derivatives

ERα controls the breast tissue development and progression of breast cancer. In our search for novel compounds to target Estrogen Receptor Alpha Ligand-Binding Domain, we identified “N-(3-((1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide” derivatives as lead compounds. The Docking studies indicated good docking score for Metacetamol derivatives when docked into the 1XP6. A series of metacetamol derivatives have been synthesized, characterized and evaluated for cytotoxicity, anti bacterial and anti oxidant activities. Among the tested twelve hybrid compounds, “7a, 7g, 7h and 7i” derivatives showed promising cytotoxicity with IC50 value of 50 value of 30 μM, whereas Compounds “7a, 7b, 7c, 7d, 7g, 7j, 7k and 7l” showed moderate anti bacterial activity with the MIC value of 300 μM.

Design and synthesis of novel diosgenin-triazole hybrids targeting inflammation as potential neuroprotective agents

Alzheimer's disease is a progressive neurodegenerative disease, and its incidence is expected to increase as the global population ages. Recent studies provide increasing evidence that inflammation plays a key role in the pathogenesis and progression of AD. Diosgenin, an active ingredient in Dioscorea nipponica Makino, is a promising bioactive lead compound in the treatment of Alzheimer's disease, which exhibited anti-inflammatory activity. To search for more efficient anti-Alzheimer agents, a series of novel diosgenin-triazolyl hybrids were designed, synthesized, and their neuroprotective effects against oxygen-glucose deprivation-induced neurotoxicity and LPS-induced NO production were evaluated. Most of these new hybrids displayed better activities than DIO. In particular, the promising compound L6 not only demonstrated an excellent neuroprotective effect but also showed the best anti-inflammatory activity. The structure-activity relationship study illustrated that the introduction of benzyl or phenyl triazole did improve the activity, and the introduction of benzyl triazole was better than that of phenyl triazole. The results we obtained showed that the diosgenin skeleton could be a promising structural template for the development of new anti-Alzheimer drug candidates, and compound L6 has the potential to be an important lead compound for further research.

Synthesis and muscarinic acetylcholine receptor (mAChR) antagonist activity of substituted piperazine-triazoles

This study describes synthesis of a series of piperazine-triazole derivatives and their ex vivo evaluation for preliminary muscarinic acetylcholine receptor (mAChR) blocking activity on rat ileum model. A molecule based on benzonitrile piperazine triazole scaffold showed good tissue relaxation and blocking of neurotransmitter ACh in the ex vivo experiment. Graphic abstract: [Figure not available: see fulltext.]

Design, synthesis, and evaluation of metronidazole-1,2,3-triazole derivatives as potent urease inhibitors

A new series of metronidazole-1,2,3-triazole derivatives 6a–o was synthesized and evaluated as Helicobacter pylori urease inhibitors. All the synthesized compounds were more potent than standard inhibitor thiourea against urease. Among the synthesized compounds, compound 6f (IC50 = 1.975 ± 0.25?μM) with inhibitory activity around 11-fols more than thiourea (IC50 = 22.00 ± 0.14?μM) was the most potent compound. Kinetic study of this compound revealed that compound 6f inhibited urease in an uncompetitive mode. Based on molecular modeling study, compound 6f pointed toward the bi-nickel center and stabilized by H-bond and T-shape π–π hydrophobic interactions with the critical residues His492 and Asp633. Moreover, it anchored to the helix-turn-helix motif in the active site cavity through interaction with His593 and Arg609. Consequently, it proposed that compound 6f through stabilization of active site flap inhibited urease activity.

Synthesis of 1,2,3,triazole modified analogues of hydrochlorothiazide via click chemistry approach and in-vitro α-glucosidase enzyme inhibition studies

The current study was aimed to discover potent inhibitors of α-glucosidase enzyme. A 25 membered library of new 1,2,3-triazole derivatives of hydrochlorothiazide (1) (HCTZ, a diuretic drug also being used for the treatment of high blood pressure) was synt

Anti-Lung Cancer Activities of 1,2,3-Triazole Curcumin Derivatives via Regulation of the MAPK/NF-κB/STAT3 Signaling Pathways

In this study, a series of curcumin derivatives containing 1,2,3-triazole were designed and synthesized, and their inhibitory activities against the proliferation of lung cancer cells were studied. Compound 5 k (3,4-dichlorobenzyltriazole methyl curcumin)

Synthesis and in vitro cytotoxicity and antibacterial activity of novel1,2,3-triazol-5-yl-phosphonates

Novel1,2,3-triazol-5-yl-phosphonates were prepared by the copper(I)-catalyzed domino reaction of phenylacetylene, organic azides and dialkyl phosphites. The process was optimized on the synthesis of the dibutyl (1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)phosphonate in respect of the catalyst, the base and the solvent, as well as of the reaction parameters (molar ratio of the starting materials, atmosphere, temperature and reaction time). The method elaborated could be applied to a range of organic azides and dialkyl phosphites, which confirmed the large scope and the functional group tolerance. The in vitro cytotoxicity on different cell lines and the antibacterial activity of the synthesized1,2,3-triazol-5-yl-phosphonates was explored. According to the IC50 values determined, only modest antibacterial effect was detected, while some derivatives showed moderate activity against human promyelocytic leukemia HL-60 cells.

P-benzoquinone diazide core skeleton derivative as well as preparation method and application thereof

The invention relates to a p-benzoquinone diazide core skeleton derivative and a preparation method and application, thereof, belongs to. the field of organic chemistry, and can effectively treat-ovarian-ovarian cancer-carcinoma STAT3-ovarian, cancer-ATG4

Design, synthesis, biological evaluation and molecular docking study of novel pyridoxine-triazoles as anti-Alzheimer's agents

A series of multi-target natural product-pyridoxine based derivatives were designed, synthesized, characterized and evaluated as anti-Alzheimer agents. In vitro testing revealed the multi-functional properties of compounds such as inhibition of acetylcholinesterase (AChE), antioxidant and metal chelation. Among the series, 5i derivative was found most potent AChE inhibitor, possess antioxidant potential and chelating metal ions. Further binding interaction of 5i with AChE was studied using molecular docking, showed interaction with both PAS and CAS site of AChE. In silico predictions were also performed to predict toxicity and ADME properties of the molecule 5i and found within drug likeness range. Therefore, 5i could be a promising multi-functional compound that can be used for further development of novel drug for Alzheimer disease.

Design, synthesis, biological evaluation, and docking study of new acridine-9-carboxamide linked to 1,2,3-triazole derivatives as antidiabetic agents targeting α-glucosidase

A new series of acridine-9-carboxamide-1,2,3-triazole derivatives 7a-m were designed, synthesized, and evaluated as novel α-glucosidase inhibitors. Acridine-9-carboxamide-1,2,3-triazole scaffold has been designed by combination of effective moieties from potent α-glucosidase inhibitors. Most of the synthesized compounds were more potent than standard inhibitor acarbose. Among the title compounds, the most potent compounds were compounds 7j, 7k, and 7a with IC50 values of 120.2 ± 1.0, 151.1 ± 1.4, and 157.6 ± 1.6 μM, respectively (IC50 value of acarbose = 750.0 ± 10.0 μM). Docking study of the most potent compounds demonstrated that these compounds formed stable complexes with α-glucosidase active site. Anti-α-amylase assay of compounds 7j, 7k, and 7a was performed and no activity was observed. in vitro cytotoxicity assay of the latter compounds revealed that these compounds were not cytotoxic toward human normal (HDF) and cancer (MCF-7) cell lines. ADME and toxicity prediction of compounds 7j, 7k, and 7a were also performed.