20937-86-4

Usage

InChI:InChI=1/C10H7N3/c11-13-12-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H

Upstream product

• 91-59-8 naphthalen-2-ylamine 
• 93-08-3 methyl 2-naphthyl ketone 
• 32316-92-0 naphthalene-2-boronic acid 
• 39834-40-7 trans-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol 

Downstream Products

• 110032-32-1 1-(naphthalen-2-yl)-4-phenyl-1H-1,2,3-triazol-5-amine 
• 20686-65-1 2-methyloxazolo<4,5-a>naphthalene 
• 581-89-5 2-nitronaphthalene 
• 2246-42-6 2-methoxynaphthylamine 
• 226-47-1 dibenzo[a,h]phenazine 
• 13711-39-2 1-amino-2-chloronaphthalene 
• 91-59-8 naphthalen-2-ylamine 
• 582-08-1 2,2'-azonaphthalene 
• 7066-13-9 2-aminonaphthalene-1-carbonitrile 
• 3100-67-2 1-amino-2-naphthalenecarbonitrile 
• 54922-17-7 2-(diethylamino)-1-aminonaphthalene 
• 54922-15-5 4'-NN-dimethylaminobenzene-ONN-2-azoxynaphthalene 
• 2437-03-8 2-ethylaminonaphthalene 
• 6949-67-3 N-(p-anisyl)-2-naphthylamine 

Relevant academic research and scientific papers

Design, synthesis and biological studies of some new imidazole-1,2,3-triazole hybrid derivatives

Some new 4-((1H-imidazol-1-yl)diarylmethyl)-5-methyl-1-aryl-1H-1,2,3-triazoles 7a-i were designed and synthesized by the one-pot reaction of diaryl-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)methanol compounds with 1H-imidazole. The new compounds 7a-i were ch

Synthesis and biological evaluation of tetrahydroisoquinoline-derived antibacterial compounds

Antibiotic resistance is one of the greatest threats to modern medicine. Drugs that were once routinely used to treat infections are being rendered ineffective, increasing the demand for novel antibiotics with low potential for resistance. Here we report

Heterogeneous photocatalysis of azides: Extending nitrene photochemistry to longer wavelengths

The photodecomposition of azides to generate nitrenes usually requires wavelengths in the 300 nm region. In this study, we show that this reaction can be readily performed in the UVA region (368 nm) when catalyzed by Pd-decorated TiO2. In aqueous medium the reaction leads to amines, with water acting as the H source; however, in non-protic and non-nucleophilic media, such as acetonitrile, nitrenes recombine to yield azo compounds, while azirine-mediated trapping occurs in the presence of nucleophiles. The heterogeneous process facilitates catalyst separation while showing great chemoselectivity and high yields.

Chan-Lam-type Azidation and One-Pot CuAAC under CuI-Zeolite Catalysis

The copper(I)-exchanged zeolite CuI-USY proved to efficiently catalyze the direct azidation of arylboronic acids with sodium azide under simple and practical conditions, namely at room temperature under air with methanol as solvent and without any additive. This easy-to-prepare and cheap catalytic material has been demonstrated to be recyclable and the mild azidation conditions further showed good functional-group tolerance, leading to a variety of substituted (hetero)aryl azides (18 examples). Interestingly, the azidation reaction has been successfully coupled to a CuAAC reaction, thus allowing access to triazoles from arylboronic acids via a one-pot CuI-catalyzed process.

Nucleophilic Iron Complexes in Proton-Transfer Catalysis: An Iron-Catalyzed Dimroth Cyclocondensation

The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) is an active catalyst in C?H-amination but also in proton-transfer catalysis. Herein, we describe the successful use of this complex as a proton-transfer catalyst in the cyclocondensation reaction between azides and ketones to the corresponding 1,2,3-triazoles. Cross-experiments indicate that the proton-transfer catalysis is significantly faster than the nitrene-transfer catalysis, which would lead to the C?H amination product. An example of a successful sequential Dimroth triazole–indoline synthesis to the corresponding triazole-substituted indolines is presented.

Small Molecule Inhibition of MicroRNA miR-21 Rescues Chemosensitivity of Renal-Cell Carcinoma to Topotecan

Chemical probes of microRNA (miRNA) function are potential tools for understanding miRNA biology that also provide new approaches for discovering therapeutics for miRNA-associated diseases. MicroRNA-21 (miR-21) is an oncogenic miRNA that is overexpressed in most cancers and has been strongly associated with driving chemoresistance in cancers such as renal cell carcinoma (RCC). Using a cell-based luciferase reporter assay to screen small molecules, we identified a novel inhibitor of miR-21 function. Following structure-activity relationship studies, an optimized lead compound demonstrated cytotoxicity in several cancer cell lines. In a chemoresistant-RCC cell line, inhibition of miR-21 via small molecule treatment rescued the expression of tumor-suppressor proteins and sensitized cells to topotecan-induced apoptosis. This resulted in a >10-fold improvement in topotecan activity in cell viability and clonogenic assays. Overall, this work reports a novel small molecule inhibitor for perturbing miR-21 function and demonstrates an approach to enhancing the potency of chemotherapeutics specifically for cancers derived from oncomir addiction.

Stereospecific photochemistry of Δ2-1,2,3-triazolines in solution and in the solid state: Scope and mechanistic studies

The stereospecific photochemistry of ten N-aryl-substituted cis- or trans-Δ2-1,2,3-triazolines to form the corresponding cis- or trans-aziridines was investigated both in solution and in the solid-state. We found that photochemical reactions in the solid state are more stereospecific than in solution for the 8 crystalline Δ2-1,2,3-triazolines. Additionally, triplet sensitization for some triazolines results in triplet biradicals, which provide the more thermodynamically favored trans-aziridine regardless of the starting triazoline stereochemistry. Product analyses as a function of temperature and solvent polarity suggest that the electronic excitation of the Δ2-1,2,3-triazolines results in the formation of a 1,3-biradical intermediate.

A novel triazole derivative of betulinic acid induces extrinsic and intrinsic apoptosis in human leukemia HL-60 cells

In an attempt to arrive at more potent cytotoxic agent than the bioactive natural product betulinic acid, influence of small structural modifications of its 1, 2, 3 triazole derivatives tethered at C-28 and both C3, C-28 using click chemistry approach has been studied. The chemically characterized triazoles have been screened for in vitro cytotoxicity against four human cancer cell lines HL-60, MiaPaCa-2, PC-3 and A549 which has allowed to identify triazole derivative 28{1N (4-fluoro phenyl)-1H-1, 2, 3-triazol-4-yl} methyloxy betulinic ester having better potency profile than the parent compound with IC50 values in the range of 5-7 μM. It caused disruption of mitochondrial membrane potential, rendered Bcl-2 cleavage, Bax translocation and decrease Bcl-2/Bax ratio. These events are accompanied by activation of caspases -9, -3, which cleave the PARP-1. It also induces caspase-8, which is involved in extrinsic apoptotic pathway. Therefore, it induces apoptosis through both intrinsic and extrinsic pathways in human leukemia HL-60 cells.

Convenient and efficient synthesis of disubstituted piperazine derivatives by catalyst-free, atom-economical and tricomponent domino reactions

One-pot, atom-economical, catalyst-free and tri-component domino reactions are applied to the diversity-oriented synthesis (DOS) of disubstituted piperazine derivatives under mild conditions with moderate to high yields. This protocol exhibits potential a

The synthesis of some new (S)-1-aryl-N-(1-hydroxy-3-phenylpropan-2-yl)-5- methyl-1H-1,2,3-triazole-4-carboxamide

Some new (S)-1-aryl-N-(1-hydroxy-3-phenylpropan-2-yl)-5-methyl-1 H-1,2,3-triazole-4-carboxamides 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j have been synthesized and established by 1H and 13C NMR, IR, MS spectra, CHN analyses, and x-ray