title: New procedure to mask the 2,3-pi bond of the indole nucleus and its application to the preparation of potent opioid receptor agonists with a Corynanthe skeleton.
abstract: Treatment of indole alkaloids with hypervalent iodine in the presence of ethylene glycol provides 2,3-ethylene glycol bridged adducts that could be converted into the original indoles under mild reductive conditions. This procedure, which involves masking of the reactivity of the indole nucleus at the beta-position, was utilized for the modification of the benzene ring of the indoline derivative and was applied to the preparation of potent opioid receptor agonists with the Corynanthe skeleton. [reaction: see text]
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, Chiba 263-8522, Japan. takayama@p.chiba-u.ac.jp
authors.forename: Hiromitsu
authors.initials: H
authors.lastname: Takayama
authors.forename: Kaori
authors.initials: K
authors.lastname: Misawa
authors.forename: Naoki
authors.initials: N
authors.lastname: Okada
authors.forename: Hayato
authors.initials: H
authors.lastname: Ishikawa
authors.forename: Mariko
authors.initials: M
authors.lastname: Kitajima
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Hatori
authors.forename: Toshihiko
authors.initials: T
authors.lastname: Murayama
authors.forename: Sumphan
authors.initials: S
authors.lastname: Wongseripipatana
authors.forename: Kimihito
authors.initials: K
authors.lastname: Tashima
authors.forename: Kenjiro
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Syunji
authors.initials: S
authors.lastname: Horie
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D000818:Animals; D019855:Ethylene Glycol / Q000737:chemistry; D006168:Guinea Pigs; D007082:Ileum / Q000187:drug effects; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry; D032065:Mitragyna / Q000737:chemistry; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D032068:Pausinystalia; D011758:Pyrroles / Q000138:chemical synthesis; D011957:Receptors, Opioid / Q000819:agonists*
chemical_list: D000470:Alkaloids; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles; D011758:Pyrroles; D011957:Receptors, Opioid; D007455:Iodine; D019855:Ethylene Glycol