87736-85-4

Usage

Uses

Used in Photoaffinity Probes:
3-(4-tolyl)-3-(trifluoromethyl)diazirine is used as a photoaffinity probe in various research applications. Photoaffinity probes are molecules that can covalently bind to a target molecule upon exposure to light, allowing for the study of the target's structure, function, and interactions with other molecules. The unique structure of 3-(4-tolyl)-3-(trifluoromethyl)diazirine, with its diazirine ring and functional groups, makes it suitable for this purpose, as it can be designed to specifically interact with and label target molecules of interest.

InChI:InChI=1/C9H7F3N2/c1-6-2-4-7(5-3-6)8(13-14-8)9(10,11)12/h2-5H,1H3

Upstream product

• 87736-82-1 3-(4-methylphenyl)-3-trifluoromethyldiaziridine 
• 87736-79-6 2,2,2-trifluoro-1-(4-methylphenyl)-1-ethanone O-(p-tolylsulfonyl)oxime 
• 106-38-7 para-bromotoluene 
• 87736-79-6 C₁₆H₁₄F₃NO₃S 
• 108-88-3 toluene 
• 75703-25-2 2,2,2-trifluoro-1-(4-methylphenyl)-1-ethanone oxime 
• 75703-25-2 2,2,2-trifluoro-1-(4-methylphenyl)-1-ethanone oxime 
• 394-59-2 2,2,2-trifluoro-1-(p-tolyl)ethanone 

Downstream Products

• 92367-11-8 3-[4'-(bromomethyl)phenyl]-3-(trifluoromethyl)-3H-diazirine 
• 85559-46-2 4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzoic acid 
• 152540-05-1 [4-(3-Trifluoromethyl-3H-diazirin-3-yl)-phenyl]-methanethiol 
• 152540-04-0 3-(4-((Acetylthio)methyl)phenyl)-3-(trifluoromethyl)-3H-diazirine 
• 87736-88-7 3-[4-(hydroxymethyl)phenyl]-3-trifluoromethyl-3H-diazirine 
• 204978-53-0 4-(3-Trifluoromethyl-3H-diazirin-3-yl)-benzoyl fluoride 
• 204978-55-2 C₉H₄⁽³⁾H₂BrF₃N₂ 
• 204978-54-1 C₉H₅⁽³⁾H₂F₃N₂O 
• 92367-16-3 (S)-3-[4-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine 
• 92367-18-5 L-4'-(1-azi-2,2,2-trifluoroethyl)phenylalanine methyl ester 

Relevant academic research and scientific papers

Photochemical Cyclopropenation of Alkynes with Diazirines as Carbene Precursors in Continuous Flow

An efficient synthesis of 3-trifluoromethyl-3-aryl-cyclopropenes via the cyclopropenation reaction of alkynes with photolytically generated carbenes from diazirine compounds is described. This reaction is performed in continuous flow using readily available LEDs under mild reaction conditions. This new and efficient method describes the synthesis of 25 examples of 3-trifluoromethyl-3-aryl-cyclopropenes with yields up to 97%, achieved in continuous flow with a 5 min residence time. Control experiments highlighted that diazirines are more efficient than diazo compounds for this transformation.

Engineering bromodomains with a photoactive amino acid by engaging 'Privileged' tRNA synthetases

Site-specific placement of unnatural amino acids, particularly those responsive to light, offers an elegant approach to control protein function and capture their fleeting 'interactome'. Herein, we have resurrected 4-(trifluoromethyldiazirinyl)-phenylalan

Click-Addressable Cassette for Photoaffinity Labeling

A small molecule 1 was designed to contain an alkyne, a trifluoromethyl phenyldiazirine, and a free piperidine-NH for facile conjugation to protein binding ligands. This "cassette" 1 was synthesized via a relatively direct route involving only routine steps. In this proof-of-concept study, putative ligands for carbonic anhydrase IX and for TrkC were conjugated to 1. Photoaffinity labeling was performed using purified extracellular regions of both these protein-receptors, and using cells that express these receptors (isolation via a pull-down procedure), labeling of the protein was observed in all four experiments.

Rapid Mapping of Protein Interactions Using Tag-Transfer Photocrosslinkers

Analysing protein complexes by chemical crosslinking-mass spectrometry (XL-MS) is limited by the side-chain reactivities and sizes of available crosslinkers, their slow reaction rates, and difficulties in crosslink enrichment, especially for rare, transie

Is Magnetic Bistability of Carbenes a General Phenomenon? Isolation of Simple Aryl(trifluoromethyl)carbenes in Both Their Singlet and Triplet States

p-Tolyl(trifluoromethyl)carbene and the related fluorenyl(trifluoromethyl)carbene were synthesized in solid argon and characterized by IR, UV-vis, and electron paramagnetic resonance spectroscopy as well as by quantum mechanical calculations. The carbenes

Synthesis of diazirine-based photoreactive saccharin derivatives for the photoaffinity labeling of gustatory receptors

Saccharin is one of the most common artificial sweeteners that has a bitter taste at high concentrations. Currently, there are no detailed functional analyses of these gustatory receptors. Therefore, we designed and synthesized photoreactive saccharin der

Alternative one-pot synthesis of (trifluoromethyl)phenyldiazirines from tosyloxime derivatives: Application for new synthesis of optically pure diazirinylphenylalanines for photoaffinity labeling

Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2- is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.

Synthesis and structure-activity relationship study of chemical probes as hypoxia induced factor-1α/malate dehydrogenase 2 inhibitors

A structure-activity relationship study of hypoxia inducible factor-1α inhibitor 3-aminobenzoic acid-based chemical probes, which were previously identified to bind to mitochondrial malate dehydrogenase 2, was performed to provide a better understanding of the pharmacological effects of LW6 and its relation to hypoxia inducible factor-1α (HIF-1α) and malate dehydrogenase 2 (MDH2). A variety of multifunctional probes including the benzophenone or the trifluoromethyl diazirine for photoaffinity labeling and click reaction were prepared and evaluated for their biological activity using a cell-based HRE-luciferase assay as well as a MDH2 assay in human colorectal cancer HCT116 cells. Among them, the diazirine probe 4a showed strong inhibitory activity against both HIF-1α and MDH2. Significantly, the inhibitory effect of the probes on HIF-1α activity was consistent with that of the MDH2 enzyme assay, which was further confirmed by the effect on in vitro binding activity to recombinant human MDH2, oxygen consumption, ATP production, and AMP activated protein kinase (AMPK) activation. Competitive binding modes of LW6 and probe 4a to MDH2 were also demonstrated.

Tri- and tetravalent photoactivable cross-linking agents

A modular synthesis of photoactivable cross-linking agents is described, using an aromatic core, di- or triethyleneglycol spacers and photoaffinity labeling synthons that feature either perfluorophenyl azide or aryl(trifluoromethyl)diazirine motifs. Symmetrical and nonsymmetrical trivalent structures were obtained from phloroglucinol and dopamine, respectively. Symmetrical tetravalent structures resulted from the coupling of two dopamine derivatives with oxalyl chloride. Georg Thieme Verlag Stuttgart New York.

Synthesis and pharmacological evaluation of fluorescent and photoactivatable analogues of antiplasmodial naphthylisoquinolines

The naphthylisoquinoline (NIQ) alkaloids from tropical Ancistrocladaceae and Dioncophyllaceae plants show high antiplasmodial activities in vitro and in vivo, even against chloroquine-resistant strains of the malaria pathogen. For the directed optimization of these activities, an investigation of the mode of action seems most rewarding. We have therefore embarked on the identification of the respective target protein in Plasmodium falciparum. For this purpose, we have developed a flexible pathway for the synthesis of a chemically divergent series of photoactive and fluorescent derivatives of such alkaloids and succeeded in preparing the first functionalized NIQ derivatives, 10, 12, and 35, suited for fluorescence and photoaffinity labeling experiments. Pharmacological investigations ensured that the modified alkaloid derivatives retained their antiplasmodial activity. The work may pave the way for a further improvement of the activity of these natural products and will thus increase their pharmacological potential as a valuable lead structure against the widespread tropical disease malaria.