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.
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]
Takayama
Hiromitsu
H
Graduate School of Pharmaceutical Sciences, Chiba University, Chiba 263-8522, Japan. takayama@p.chiba-u.ac.jp
Misawa
Kaori
K
Okada
Naoki
N
Ishikawa
Hayato
H
Kitajima
Mariko
M
Hatori
Yoshio
Y
Murayama
Toshihiko
T
Wongseripipatana
Sumphan
S
Tashima
Kimihito
K
Matsumoto
Kenjiro
K
Horie
Syunji
S
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*
D000470:Alkaloids; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles; D011758:Pyrroles; D011957:Receptors, Opioid; D007455:Iodine; D019855:Ethylene Glycol