title: Synthesis of 2,6-aceanthrylenedione, a cyclic vinylog of anthraquinone.
abstract: 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.
authors.affiliation: Institute of Pharmaceutical and Medicinal Chemistry, Westphalian Wilhelms-University, Hittorfstrasse 58-62, D-48149 Münster, Germany. prinzh@uni-muenster.de
authors.forename: Helge
authors.initials: H
authors.lastname: Prinz
authors.forename: Konrad J
authors.initials: KJ
authors.lastname: Böhm
authors.forename: Klaus
authors.initials: K
authors.lastname: Müller
mesh_terms: D000873:Anthracenes / Q000737:chemistry*; D000880:Anthraquinones / Q000138:chemical synthesis*; D003500:Cyclization; D050257:Tubulin Modulators
chemical_list: D000873:Anthracenes; D000880:Anthraquinones; D050257:Tubulin Modulators; C044587:aceanthrylene