title: Synthesis and analgesic activity of stereoisomers of cis-fluoro-ohmefentanyl.
abstract: Four stereoisomers 1a-d of cis-fluoro-ohmefentanyl have been synthesized. Their absolute configurations were determined by X-ray analysis of (3S,4R,2'S)-(-)-cis-I d. The analgesic activity (mice, sc, hot plate) revealed extreme stereodifferences. The ED50 value of (3R,4S,2'S)-(+)-cis-I (1a) was 0.000774 mg/kg (17958 times more potent than that of morphine), while the corresponding antipode 1c was almost inactive.
authors.affiliation: Shanghai Institute of Materia Medical, Chinese Academy of Sciences, Shanghai, Guangzhou, Guangdon, PR China. zouyong@gic.ac.cn
authors.forename: Zou
authors.initials: Z
authors.lastname: Yong
authors.forename: Wu
authors.initials: W
authors.lastname: Hao
authors.forename: Yuan
authors.initials: Y
authors.lastname: Weifang
authors.forename: Dai
authors.initials: D
authors.lastname: Qiyuan
authors.forename: Chen
authors.initials: C
authors.lastname: Xinjian
authors.forename: Jin
authors.initials: J
authors.lastname: Wenqiao
authors.forename: Zhu
authors.initials: Z
authors.lastname: Youcheng
mesh_terms: D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D018360:Crystallography, X-Ray; D005283:Fentanyl / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D009020:Morphine / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000701:Analgesics, Opioid; D007202:Indicators and Reagents; C483144:cis-fluoro-ohmefentanyl; D009020:Morphine; D005283:Fentanyl