title: [Synthesis and analgesic activity of 1-substituted derivatives of 4-methoxycarbonyl-4-N-propionylanilinepiperidine].
abstract: In this paper, the synthesis and analgesic activities of a series of 1-substituted derivatives of N-[1-(2-phenylethyl)-4-methoxycarbonyl-4-piperidinyl]-N-propionylanil ine (4-methoxycarbonyl fentanyl) are reported. Preliminary pharmacological results showed that most compounds in this series exhibited typical morphine-like action and that replacement of beta-phenyl group in the 1-position of piperidine ring of 4-methoxycarbonyl fentanyl by some substituents e.g., some substituted vinyl groups, heterocyclic (or alcyclic) radicals, alkyl groups or N-methyl-anilino groups, can keep strong analgesic activity. Especially, some substituted vinyl groups were found to be effective groups which could replace 1-beta-phenyl group of 4-methoxycarbonyl fentanyl. Compounds N-[1-(3, 4-dimethyl-3-pentenyl)-4-methoxycarbonyl-4-piperidinyl]-N- propionylaniline(1321) and N-[1-(4-methyl-3-pentenyl)-4-methoxycarbonyl-4-piperidinyl]-N- propionylaniline(1302) exhibited higher analgesic activity than that of 4-methoxycarbonyl fentanyl.
authors.affiliation: Institute of Pharmaceutical Chemistry, PLA, Beijing.
authors.forename: Y L
authors.initials: YL
authors.lastname: Yang
authors.forename: X W
authors.initials: XW
authors.lastname: Zhu
authors.forename: G Z
authors.initials: GZ
authors.lastname: Zhu
authors.forename: Z J
authors.initials: ZJ
authors.lastname: Yang
authors.forename: Y
authors.initials: Y
authors.lastname: Li
authors.forename: S Y
authors.initials: SY
authors.lastname: Zhao
authors.forename: C H
authors.initials: CH
authors.lastname: Chen
authors.forename: K G
authors.initials: KG
authors.lastname: Zhang
mesh_terms: D000701:Analgesics, Opioid / Q000138:chemical synthesis*; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D005283:Fentanyl / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D051379:Mice
chemical_list: D000701:Analgesics, Opioid; C017114:carfentanil; D005283:Fentanyl