81340-56-9

Usage

Uses

Used in Chemical Biology Research:
3-(trifluoromethyl)-3-(3-iodophenyl)diazirine is used as a photochemical probe for studying the structure and function of biomolecules due to its reactivity upon UV light exposure.
Used in Drug Discovery Research:
3-(trifluoromethyl)-3-(3-iodophenyl)diazirine is used as a tool for photoaffinity labeling to help identify and characterize drug targets, contributing to the development of new therapeutic agents.
Used in Protein Crosslinking:
3-(trifluoromethyl)-3-(3-iodophenyl)diazirine is used as a crosslinking agent to study protein interactions and conformational changes, which is vital for understanding protein function and dynamics.
Used in Photochemical Probes Development:
3-(trifluoromethyl)-3-(3-iodophenyl)diazirine is used in the development of photochemical probes to investigate biological processes and mechanisms at a molecular level, providing insights into disease pathways and potential therapeutic interventions.

InChI:InChI=1/C8H4F3IN2/c9-8(10,11)7(13-14-7)5-2-1-3-6(12)4-5/h1-4H

Upstream product

• 626-00-6 1,3-Diiodobenzene 
• 23516-86-1 2,2,2-trifluoro-1-(3-iodophenyl)ethan-1-one 

Downstream Products

• 1390672-65-7 5-allyl-1-methyl-5-[3-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]pyrimidine-2,4,6-trione 
• 1390672-66-8 1-methyl-5-prop-2-ynyl-5-[3-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]pyrimidine-2,4,6-trione 
• 1390672-68-0 5-allyl-1-methyl-5-[3-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]pyrimidine-2,4,6-trione 
• 1390672-67-9 5-allyl-1-methyl-5-[3-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]pyrimidine-2,4,6-trione 

Relevant academic research and scientific papers

Allyl m -trifluoromethyldiazirine mephobarbital: An unusually potent enantioselective and photoreactive barbiturate general anesthetic

We synthesized 5-allyl-1-methyl-5-(m-trifluoromethyl-diazirynylphenyl) barbituric acid (14), a trifluoromethyldiazirine-containing derivative of general anesthetic mephobarbital, separated the racemic mixture into enantiomers by chiral chromatography, and determined the configuration of the (+)-enantiomer as S by X-ray crystallography. Additionally, we obtained the 3H-labeled ligand with high specific radioactivity. R-(-)-14 is an order of magnitude more potent than the most potent clinically used barbiturate, thiopental, and its general anesthetic EC50 approaches those for propofol and etomidate, whereas S-(+)-14 is 10-fold less potent. Furthermore, at concentrations close to its anesthetic potency, R-(-)-14 both potentiated GABA-induced currents and increased the affinity for the agonist muscimol in human α1β2/3γ2L GABAA receptors. Finally, R-(-)-14 was found to be an exceptionally efficient photolabeling reagent, incorporating into both α1 and β3 subunits of human α1β3 GABA A receptors. These results indicate R-(-)-14 is a functional general anesthetic that is well-suited for identifying barbiturate binding sites on Cys-loop receptors.