57958-48-2Relevant academic research and scientific papers
Evaluation of agonistic activity of fluorinated and nonfluorinated fentanyl analogs on μ-opioid receptor using a cell-based assay system
Kanamori, Tatsuyuki,Okada, Yuki,Segawa, Hiroki,Yamamuro, Tadashi,Kuwayama, Kenji,Tsujikawa, Kenji,Iwata, Yuko Togawa
, p. 159 - 161 (2021/02/09)
The agonistic activity of fluorinated and nonfluorinated fentanyl analogs on μ-opioid receptor was investigated using a cell-based assay system. Based on the activity, fentanyl analogs were ranked as follows: fentanyl>isobutyrylfentanyl≈butyrylfentanyl≈methoxyacetylfentanyl>acetylfentanyl. However, among the fentanyl analogs fluorinated on the Nphenyl ring, 2-fluoro analogs and 3-fluoro analogs showed the strongest and weakest activities, respectively. These results suggest that the 2-fluorinated isomers of fentanyl analogs are more likely to cause poisoning.
Fentanyl family at the mu-opioid receptor: Uniform assessment of binding and computational analysis
Lipiński, Piotr F.J.,Kosson, Piotr,Matalińska, Joanna,Roszkowski, Piotr,Czarnocki, Zbigniew,Jarończyk, Ma?gorzata,Misicka, Aleksandra,Dobrowolski, Jan Cz.,Sadlej, Joanna
, (2019/02/26)
Interactions of 21 fentanyl derivatives with μ-opioid receptor (μOR) were studied using experimental and theoretical methods. Their binding to μOR was assessed with radioligand competitive binding assay. A uniform set of binding affinity data contains val
A new method for the synthesis of amides from imines
Ghaffarzadeh, Mohammad,Joghan, Somaye Shahrivari,Faraji, Fereshteh
experimental part, p. 203 - 206 (2012/03/07)
An efficient and straightforward method for the synthesis of amides by the reaction of imines and anhydrides in the presence of Et3SiH/Zn is reported. Mild reaction conditions, good yields of products, short reaction times, and operational simplicity are advantages of this procedure.
Synthesis and investigations of double-pharmacophore ligands for treatment of chronic and neuropathic pain
Vardanyan, Ruben,Vijay, Gokhale,Nichol, Gary S.,Liu, Lu,Kumarasinghe, Isuru,Davis, Peg,Vanderah, Todd,Porreca, Frank,Lai, Josephine,Hruby, Victor J.
experimental part, p. 5044 - 5053 (2009/12/04)
Acids 9a-f as possible bivalent ligands designed as a structural combination of opioid μ-agonist (Fentanyl) and NSAID (Indomethacin) activities and produced compounds which were tested as analgesics. The obtained series of compounds exhibits low affinity and activity both at opioid receptors and as cyclooxygenase (COX) inhibitors. One explanation of the weak opioid activity could be stereochemical peculiarities of these bivalent compounds which differ significantly from the fentanyl skeleton. The absence of significant COX inhibitory properties could be explained by the required substitution of an acyl fragment in the indomethacin structure for 4-piperidyl.
Aminohaloborane in Organic Synthesis. IX. Exclusive ortho Acylation Reaction of N-Monoaminoalkylanilines
Adachi, Makoto,Sasakura, Kazuyuki,Sugasawa, Tsutomu
, p. 1826 - 1835 (2007/10/02)
The exclusive ortho acylation reaction of aniline derivatives using boron trichloride made possible the one-step synthesis of 2-acyl-N-monoaminoalkylanilines (1) and the corresponding imines (2) from N-monoaminoalkylanilines, even in the case of compounds with a bulky substituent at the nitrogen atom.Conventional methods only give 1 via elaborate procedures.Keywords: regioselective reaction; 2-acylaniline derivative; 2-acylaniline-imine derivative; boron trichloride
