31656-91-4

Usage

InChI:InChI=1/C12H9N3/c13-15-14-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H

Upstream product

• 92-67-1 4-phenylalanine 
• 144432-80-4 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 5122-94-1 4-biphenylboronic acid 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 1591-31-7 4-iodo-biphenyl 
• 622-37-7 Phenyl azide 
• 98-80-6 phenylboronic acid 
• 4163-91-1 4-Xenyldiazoniumchlorid 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 77116-66-6 biphenyl-4-yl-triphenylphosphoranyliden-amine 
• 94258-14-7 4-Methoxy-4'-phenyl-azobenzol 
• 5326-53-4 1,2-di([1,1'-biphenyl]-4-yl)diazene 
• 92-67-1 4-phenylalanine 
• 41789-48-4 2-(diethylamino)-5-phenyl-3H-azepine 
• 142757-76-4 4,4'diphenyl azobenzene 
• 42860-77-5 4-hydroxy-4-phenyl-cyclohexa-2,5-dienone 
• 243668-39-5 p-biphenylylnitrenium cation 
• 1292809-57-4 (S)-1-((1-(biphenyl-4-yl)-1H-1,2,3-triazol-5-yl)methyl)-5-(2-(methoxymethyl)pyrrolidin-1-ylsulfonyl)indoline-2,3-dione 
• 1292809-49-4 (S)-1-((1-(biphenyl-4-yl)-1H-1,2,3-triazol-4-yl)methyl)-5-(2-(methoxymethyl)pyrrolidin-1-ylsulfonyl)indoline-2,3-dione 
• 1307910-53-7 C₄₁H₃₈N₆O₄ 
• 1350472-14-8 [1-NMe₂-2-CH₂OCH₂-N₃(C₆H₄Ph)C₂H-4-SiMe₃-Fc] 
• 1417405-97-0 N-decyl-3,5-bis(1-([1,1'-biphenyl]-4-yl)-1H-1,2,3-triazol-4-yl)benzamide 
• 1421275-98-0 1-(biphenyl-4-yl)-4-(phenanthren-9-yl)-1H-1,2,3-triazole 

Relevant academic research and scientific papers

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

Catalytic enantioselective synthesis of chiral spirocyclic 1,3-diketones: Via organo-cation catalysis

An SPA-triazolium bromide-catalyzed transannular C-acylation of enol lactones is presented. This methodology provides convenient access to a range of enantioenriched spirocyclic 1,3-diketones in moderate to high yields and enantioselectivities and features a broad substrate scope in terms of enol lactones. The catalytic capability of this triazolium salt catalyst is also demonstrated in this enantioselective transformation, which could inspire its further application. This journal is

Optimizing the aryl-triazole of cjoc42 for enhanced gankyrin binding and anti-cancer activity

Gankyrin is an oncoprotein overexpressed in numerous cancer types and appears to play a key role in regulating cell proliferation, cell growth, and cell migration. These roles are largely due to gankyrin's protein-protein interaction with the 26S proteaso

Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts

Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2+ TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.

Aryl Azides as Forgotten Electrophiles in the Van Leusen Reaction: A Multicomponent Transformation Affording 4-Tosyl-1-arylimidazoles

Considering aryl azides as electrophilic partners for the TosMIC mediated Van Leusen reaction, a novel multicomponent synthesis of 4-tosyl-1-arylimidazoles is reported. In this transformation, two molecules of TosMIC participate in the reaction mechanism

Triazole naphthoquinone connected aromatic (heterocyclic) ring derivative

The invention belongs to the field of chemical medicine, particularly relates to a micromolecule capable of resisting malignant tumor, acute leukemia and arthritis, multiple sclerosis and immunological rejection and a preparation and application of the mi

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.

Alkyne-azide cycloaddition analogues of dehydrozingerone as potential anti-prostate cancer inhibitors: Via the PI3K/Akt/NF-kB pathway

Herein, we report the isolation and synthetic modification of dehydrozingerone (DHZ, 1), a secondary metabolite present in the rhizome of Zingiber officinale. We synthesized O-propargylated dehydrozingerone, which was subsequently coupled by alkyne-azide cycloaddition (3-20) using click chemistry. The compounds (1-20) were evaluated for their in vitro cytotoxic activity in a panel of three cancer cell lines. Among all the DHZ derivatives, 3, 6, 7, 8, 9 and 15 displayed potent cytotoxic potential with an IC50 value ranging from 1.8-3.0 μM in MCF-7, PC-3 and HCT-116 cell lines. Furthermore, compound 7 has proven to be the most potent cytotoxic compound in all the three distinct cancer cell lines and also demonstrated significant anti-invasive potential in prostate cancer. The mechanistic study of compound 7 showed that it not only suppressed the AKT/mTOR signalling which regulates nuclear transcription factor-NF-kB but also augmented the expression of anti-invasive markers E-cadherin and TIMP. Compound 7 significantly decreased the expression of pro-invasive markers vimentin, MMP-2 and MMP-9, respectively. This study underscores an efficient synthetic approach employed to evaluate the structure-activity relationship of dehydrozingerone (1) in search of potential new anticancer agents.

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.