Synthesis of lakshminine and antiproliferative testing of related oxoisoaporphines.
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.
Faculty of Basic Sciences, Metropolitan Educational Sciences University, Avenida J.P. Alessandri 774, Ñuñoa, Santiago, Chile. vicente.castro@umce.cl
Vicente
V
Castro-Castillo
Marco
M
Rebolledo-Fuentes
Cristina
C
Theoduloz
Bruce K
BK
Cassels
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001060:Aporphines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D001060:Aporphines; C474697:lakshminine