912286-42-1Relevant articles and documents
Synthesis and evaluation of 3-aminopropionyl substituted fentanyl analogues for opioid activity
Petrov, Ravil R.,Vardanyan, Ruben S.,Lee, Yeon S.,Ma, Shou-wu,Davis, Peg,Begay, Lucinda J.,Lai, Josephine Y.,Porreca, Frank,Hruby, Victor J.
, p. 4946 - 4950 (2006)
An enkephalin analogue coupled to 'aminofentanyl' has been synthesized and tested for biological activities at the μ and δ opioid receptors. Aminofentanyl which represents a structural derivative of fentanyl has been synthesized by acylation of 1-(2-phenethyl)-4-(N-anilino)piperidine with phthaloyl protected β-alaninyl chloride in the presence of DIPEA, followed by deprotection with hydrazine hydrate. Aminofentanyl has also been successfully acylated with ethyl isocyanate, various acid anhydrides, to further investigate structure-activity relationships of these new fentanyl derivatives. Among the new derivatives compound 7 which carries a Tyr-d-Ala-Gly-Phe opioid message sequence showed good opioid affinity (1 nM at both δ and μ opioid receptors) and bioactivity (34.9 nM in MVD and 42 nM in GPI/LMMP bioassays).