title: The first total syntheses of (±)-norphoebine, dehydrophoebine, oxophoebine, dehydrocrebanine, oxocrebanine and uthongine and their cytotoxicity against three human cancer cell lines.
abstract: The first total syntheses of (±)-norphoebine, dehydrophoebine, oxophoebine, dehydrocrebanine, oxocrebanine and uthongine have been achieved. The crucial step involved the formation of ring C by a microwave-assisted direct biaryl coupling to produce the aporphine skeleton in high yields. The synthetic alkaloids were evaluated for their cytotoxicity against three human cancer cell lines MCF7, KB and NCI-H187. The results showed that uthongine was the best candidate of the series and it exhibited cytotoxicity against a human breast cancer MCF7 line with an IC50 = 3.05 μM.
authors.affiliation: a Faculty of Science, Department of Chemistry , Silpakorn University , Nakorn Pathom , Thailand.
authors.forename: Kanok-On
authors.initials: KO
authors.lastname: Rayanil
authors.affiliation: a Faculty of Science, Department of Chemistry , Silpakorn University , Nakorn Pathom , Thailand.
authors.forename: Cholthicha
authors.initials: C
authors.lastname: Prempree
authors.affiliation: a Faculty of Science, Department of Chemistry , Silpakorn University , Nakorn Pathom , Thailand.
authors.forename: Surachai
authors.initials: S
authors.lastname: Nimgirawath
mesh_terms: D000470:Alkaloids; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001060:Aporphines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D020128:Inhibitory Concentration 50; D007624:KB Cells; D061986:MCF-7 Cells; D008872:Microwaves; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents; D001060:Aporphines; C086774:oxophoebine
keywords: Oxophoebine; cytotoxic activity; oxocrebanine; total syntheses; uthongine