title: Synthesis and cytotoxic activity of the heptaphylline and 7-methoxyheptaphylline series.
abstract: Nineteen carbazole alkaloids modified from heptaphylline (I) and 7-methoxyheptaphylline (II) isolated from Clausena harmandiana were synthesized. Among these derivatives, Ih and IIi showed cytotoxicity against the NCI-H187 cell line with IC(50) values of 0.02 and 0.66 μM, respectively, which are about 138 and 4 fold stronger than the ellipticine standard. In addition, oxime Ih displayed cytotoxicity against KB cells with an IC(50) value of 0.17 μM which is about 10 times stronger than the ellipticine. This compound demonstrated weak cytotoxicity against Vero cells (IC(50) = 66.01 μM). The results show convincingly that Ih may be a promising lead for the development of cytotoxic agents.
authors.affiliation: Natural Products Research Unit, Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand.
authors.forename: Tula
authors.initials: T
authors.lastname: Thongthoom
authors.forename: Pawantree
authors.initials: P
authors.lastname: Promsuwan
authors.forename: Chavi
authors.initials: C
authors.lastname: Yenjai
mesh_terms: D000818:Animals; D002227:Carbazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002522:Chlorocebus aethiops; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D017550:Spectroscopy, Fourier Transform Infrared; D014709:Vero Cells
chemical_list: C557425:7-methoxyheptaphylline; D002227:Carbazoles; C557424:heptaphylline