[Preparation and structural elucidation of insularine-N-oxides].
Oxidation of insularine (I) with m-chloroperbenzoic acid yielded four insularine-N-oxides. Two of them are identical in every respect with our insularine-2 beta-N-oxide (II) and insularine-2' beta-N-oxide (III), two rare examples of naturally occurring head-to-tail bisbenzylisoquinoline N-oxides newly isolated from Cyclea sutchuenensis, which confirmed the structures of the two novel natural N-oxides. The other two are new compounds and their structures have been established as insularine-2' alpha-N-oxide (IV) and insularine-2 beta,2' beta-N, N-dioxide (V), on the basis of spectral data (UV, IR, 1HNMR, NOEDS AND MS) analysis.
Lai
S
S
School of Pharmacy, West China University of Medical Sciences, Chengdu.
Zhao
T F
TF
Wang
X K
XK
Shizuri
Y
Y
Yamamura
S
S
D003497:Cyclic N-Oxides / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure
D003497:Cyclic N-Oxides; D004365:Drugs, Chinese Herbal; D007546:Isoquinolines; C085234:insularine-2-N-oxide