title: Synthesis and biological evaluation of 10,11-methylenedioxy-14-azacamptothecin.
abstract: [reaction: see text] 10,11-Methylenedioxy-14-azacamptothecin, a potent analogue of the antitumor agent camptothecin (CPT), has been prepared via a key condensation between AB and DE ring precursors. The biological testing of this compound validated a strategy for modulation of the off-rate of camptothecin analogues from the topoisomerase-DNA-CPT ternary complex via structural modification.
authors.affiliation: Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA.
authors.forename: Mark A
authors.initials: MA
authors.lastname: Elban
authors.forename: Wenyue
authors.initials: W
authors.lastname: Sun
authors.forename: Brian M
authors.initials: BM
authors.lastname: Eisenhauer
authors.forename: Rong
authors.initials: R
authors.lastname: Gao
authors.forename: Sidney M
authors.initials: SM
authors.lastname: Hecht
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002166:Camptothecin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004247:DNA / Q000737:chemistry; D004264:DNA Topoisomerases, Type I / Q000235:genetics; D004354:Drug Screening Assays, Antitumor; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D059004:Topoisomerase I Inhibitors
chemical_list: C519985:10,11-methylenedioxy-14-azacamptothecin; D000972:Antineoplastic Agents, Phytogenic; D059004:Topoisomerase I Inhibitors; D004247:DNA; D004264:DNA Topoisomerases, Type I; D002166:Camptothecin