128129-42-0Relevant articles and documents
Studies on Methoxylation in the 7H-Naphtho[1,2,3-i,j] [2,7]naphthyridin-7-one System
Zjawiony, Jordan K.,Khalil, Ashraf A.,Clark, Alice M.,Hufford, Charles D.,Buolamwini, John K.
, p. 1233 - 1237 (1997)
Studies on methoxylation in the 7H-naphtho[1,2,3-i,j][2,7]naphthyridin-7-one (sampangine) system represented by 3-bromo- and 4-bromosampangine as well as sampangine itself are described. We have found that regioselectivity of nucleophilic substitution in the sampangine system can be directed by reaction conditions. Under kinetic control (lower temperatures) substitution at C-4 is the predominant reaction, regardless of whether 3-bromo or 4-bromosampangine were used. At higher temperatures, when the reaction is thermodynamically controlled, substitution of the bromine atom at C-3 predominates. This is the first reported example of nucleophilic substitution in ring A of the 7H-naphtho [1,2,3-i,j][2,7]naphthyridin-7-one system.
Copyrine alkaloids: Synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines
Peterson,Zjawiony,Liu,Hufford,Clark,Rogers
, p. 4069 - 4077 (2007/10/02)
Several A- and B-ring-substituted sampangines were synthesized and evaluated for antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens. Electrophilic halogenation provided a channel for structural elaboration of