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.
Castro-Castillo
Vicente
V
Faculty of Basic Sciences, Metropolitan Educational Sciences University, Avenida J.P. Alessandri 774, Ñuñoa, Santiago, Chile. vicente.castro@umce.cl
Rebolledo-Fuentes
Marco
M
Theoduloz
Cristina
C
Cassels
Bruce K
BK
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