title: Antinociceptive effects of N-acyloctahydropyrido[3,2,1-ij][1,6]naphthyridine in mice: structure-activity relation study of matrine-type alkaloids part II.
abstract: N-Acyloctahydropyrido[3,2,1-ij][1,6]naphthyridines were synthesized as derivatives of matrine-type alkaloids, and the structure-activity relations were examined by the acetic acid-induced abdominal contraction test. The antinociceptive potencies of N-acyloctahydropyrido[3,2,1-ij][1,6]naphthyridines were significantly lower than those of (+)-matrine. The antinociceptive effects of N-benzyloctahydropyrido[3,2,1-ij][1,6]naphthyridines are approximately 5.6 to 6.5 times less than those of N-benzoyloctahydropyrido[3,2,1-ij][1,6]naphthyridine. These findings suggest that the amide group of matrine-type alkaloids is an essential functional group that influences antinociceptive potency. The antinociceptive effect of 4c was markedly antagonized by pretreatment with Naloxone, and that of 3c partially so.
authors.affiliation: Faculty of Medicinal Chemistry, Hoshi University, Shinagawa-ku, Tokyo, Japan.
authors.forename: Seiichi
authors.initials: S
authors.lastname: Kobashi
authors.forename: Masayuki
authors.initials: M
authors.lastname: Takizawa
authors.forename: Hajime
authors.initials: H
authors.lastname: Kubo
authors.forename: Takayasu
authors.initials: T
authors.lastname: Yamauchi
authors.forename: Kimio
authors.initials: K
authors.lastname: Higashiyama
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D000700:Analgesics / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D006571:Heterocyclic Compounds; D051379:Mice; D009270:Naloxone / Q000494:pharmacology; D009292:Narcotic Antagonists / Q000494:pharmacology; D010146:Pain / Q000188:drug therapy*; D010147:Pain Measurement / Q000187:drug effects*; D011807:Quinolizines; D012020:Reflex, Abdominal / Q000187:drug effects; D013329:Structure-Activity Relationship; D000093842:Matrines
chemical_list: D000470:Alkaloids; D000700:Analgesics; D000894:Anti-Inflammatory Agents, Non-Steroidal; D006571:Heterocyclic Compounds; D009292:Narcotic Antagonists; D011807:Quinolizines; D009270:Naloxone; D000093842:Matrines