Synthesis of 2,6-aceanthrylenedione, a cyclic vinylog of anthraquinone.
The first synthesis of 2,6-aceanthrylenedione (6), a cyclic vinylog of anthraquinone and a useful starting material for the synthesis of 1-phenylaceanthrylene-2,6-diones such as 7, 8, and 9, is described. (10-Oxo-10H-anthracen-9-ylidene) acetyl chloride (5) cyclizes intramolecularly at room temperature in the presence of AlCl(3) to give 6. We found that 6 is a cytotoxic compound that inhibits tubulin polymerization.
Prinz
Helge
H
Institute of Pharmaceutical and Medicinal Chemistry, Westphalian Wilhelms-University, Hittorfstrasse 58-62, D-48149 Münster, Germany. prinzh@uni-muenster.de
Böhm
Konrad J
KJ
Müller
Klaus
K
D000873:Anthracenes / Q000737:chemistry*; D000880:Anthraquinones / Q000138:chemical synthesis*; D003500:Cyclization; D050257:Tubulin Modulators
D000873:Anthracenes; D000880:Anthraquinones; D050257:Tubulin Modulators; C044587:aceanthrylene