antofine and pergularinine

antofine has been researched along with pergularinine* in 1 studies

Other Studies

1 other study(ies) available for antofine and pergularinine

ArticleYear
Total synthesis of phenanthroindolizidine alkaloids (+/-)-antofine, (+/-)-deoxypergularinine, and their dehydro congeners and evaluation of their cytotoxic activity.
    Bioorganic & medicinal chemistry, 2008, Jun-01, Volume: 16, Issue:11

    Due to their limited natural abundance and significant biochemical effects, we synthesized the alkaloids (+/-)-antofine (1a), (+/-)-deoxypergularinine (1b), and their dehydro congeners (2 and 3) starting from the corresponding phenanthrene-9-carboxaldehydes. We also evaluated their in vitro cytotoxic activity. Compounds 1a and 1b showed significant potency against various human tumor cell lines, including a drug-resistant variant, with EC(50) values ranging from 0.16 to 16ng/mL. Structure-activity correlations of these alkaloids and some of their synthetic intermediates were also ascertained. The non-planar structure between the two major moieties, phenanthrene and indolizidine, plays a crucial role in the cytotoxic activity of phenanthroindolizidines. Increasing the planarity and rigidity of the indolizidine moiety significantly reduced potency. A methoxy group at the 2-position (1a) was more favorable for cytotoxic activity than a hydrogen atom (1b).

    Topics: Alkaloids; Bromides; Cell Line, Tumor; Chlorides; Drug Resistance, Neoplasm; Humans; Indoles; Indolizines; Isoquinolines; KB Cells; Phenanthrolines

2008