The synthesis and preliminary pharmacological evaluation of 4-methyl fentanyl.
The synthesis of 4-methyl fentanyl, a prototype of a novel class of fentanyl analogues has been effected in 5 steps, starting from N-ethoxycarbonyl-4-piperidone (approximately 20% overall yield). In the key step, N-phenylation of secondary aliphatic amide intermediare was achieved by a novel reaction, using diphenyliodonium chloride for the phenyl group transfer. Preliminary pharmacological results indicate that 4-methyl fentanyl is a super potent narcotic analgesic, about four times more potent than fentanyl.
Mićović
I V
IV
Faculty of Chemistry, University of Belgrade, FR Yugoslavia.
Ivanović
M D
MD
Vuckovic
S M
SM
Prostran
M S
MS
Dosen-Mićović
L
L
Kiricojević
V D
VD
D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D005283:Fentanyl / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship
D000701:Analgesics, Opioid; D005283:Fentanyl