Synthesis and biological evaluation of cepharadiones A and B and related dioxoaporphines.
Described herein is the first total synthesis and structural confirmation of cepharadione A, a naturally occurring DNA damaging agent. Also reported is the synthesis of cepharadione B, a closely related natural product, as well as the biological evaluation of both natural products. Finally, the preparation and biological evaluation of novel dioxoaporphine analogues is described.
Elban
Mark A
MA
Departments of Chemistry and Biology, University of Virginia, Charlottesville, VA 22904, USA.
Chapuis
Jean C
JC
Li
Mei
M
Hecht
Sidney M
SM
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001060:Aporphines / Q000138:chemical synthesis* / Q000494:pharmacology*; D001688:Biological Products / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects*; D004353:Drug Evaluation, Preclinical; D006801:Humans; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D001060:Aporphines; D001688:Biological Products; D007546:Isoquinolines; D011166:Porphyrins; C488889:cepharadione A; C457230:cepharadione B; C107018:porphine