Synthesis of Lakshminine and Antiproliferative Testing of Related Oxoisoaporphines
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Lakshminine (6-amino-1-aza-5-methoxy-7H-dibenzo[de,h]quinolin-7-one, 1) is a recent addition to the small family of oxoisoaporphine alkaloids and a member of an even smaller set bearing an amino group at C-6. This rare natural product has now been synthesized in order to have sufficient amounts for biological testing. Lakshminine, its 4-amino isomer (2), their 6- and 4-nitro precursors (8 and 10, respectively), the intermediate 5-methoxy-7H-dibenzo[de,h]quinolin-7- one (6), and the unsubstituted skeleton (11) were tested against normal human fibroblasts and three human solid tumor cell lines. Only compound 10 showed marginal antiproliferative activity.
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