1474-02-8Relevant articles and documents
TMSCF2Br-Enabled Fluorination–Aminocarbonylation of Aldehydes: Modular Access to α-Fluoroamides
Hu, Jinbo,Liu, An,Ni, Chuanfa,Xie, Qiqiang
supporting information, (2022/01/06)
A protocol for the modular assembly of the α-fluoroamide motif has been developed, which provides a practical method for the efficient synthesis of structurally diverse α-fluoroamides from easily available aldehydes and tertiary amines through a three-component fluorination–aminocarbonylation process. The key to the success of this process is taking advantage of the multiple roles of the unique difluorocarbene reagent TMSCF2Br (TMS=trimethylsilyl). The mechanism of the process involves the 1,2-fluorine and oxygen migrations of the in situ formed TMS-protected α-aminodifluoromethyl carbinol intermediates, which represents a new type of deoxyfluorination reaction.
Preparation of Fentanyl Labeled with Carbon-14
Nami,Dabiri,Shirvani,Ahmadi Faghih,Javaheri
, p. 42 - 44 (2018/03/21)
A convenient synthetic pathway for 14C labeling of fentanyl [N-(1-phenethyl-4-piperidinyl)- propionanilide], a widely used narcotic analgesic agent, with good radiochemical yield was developed.
A photochromic agonist for μ-opioid receptors
Schoenberger, Matthias,Trauner, Dirk
supporting information, p. 3264 - 3267 (2014/04/03)
Opioid receptors (ORs) are widely distributed in the brain, the spinal cord, and the digestive tract and play an important role in nociception. All known ORs are G-protein-coupled receptors (GPCRs) of family A. Another well-known member of this family, rhodopsin, is activated by light through the cis/trans isomerization of a covalently bound chromophore, retinal. We now show how an OR can be combined with a synthetic azobenzene photoswitch to gain light sensitivity. Our work extends the reach of photopharmacology and outlines a general strategy for converting Family A GPCRs, which account for the majority of drug targets, into photoreceptors. Lighting up the opioid receptor: Photofentanyl-2 is a photochromic version of the well-known analgesic fentanyl. It is a potent agonist in the dark (or when illuminated with blue light) and loses activity when irradiated with UV light. It can be used to optically control the μ-opioid receptor, converting a G-protein-coupled receptor (GPCR) into a photoreceptor.