Epoxide-containing side chains enhance antiproliferative activity of paullones.
The introduction of side chains bearing epoxide motifs into the molecular scaffold of kenpaullone and 9-trifluoromethylpaullone led to improved antiproliferative activity of the novel derivatives for human tumor cell lines. The syntheses were accomplished applying Stille coupling for the introduction of unsaturated side chains into the 2-position of the paullones and subsequently employing a hydrogen peroxide/nitrile mixture for the epoxidation of C,C-double bonds.
Xie
Xu
X
Institut für Pharmazie, Universität Hamburg, Bundesstrasse 45, D-20146 Hamburg, Germany.
Lemcke
Thomas
T
Gussio
Rick
R
Zaharevitz
Daniel W
DW
Leost
Maryse
M
Meijer
Laurent
L
Kunick
Conrad
C
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001552:Benzazepines / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D001552:Benzazepines; D004852:Epoxy Compounds; D007211:Indoles; C119620:kenpaullone