ORGN 404 |
| Pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) are a group of potent, naturally occurring antitumor antibiotics produced by Streptomyces species. These antibiotics have been proposed to covalently bond to N2 of guanine to form a neutral minor groove adduct. Tomaymycin and DC-81 are the best known examples of the PBDs. Although the natural occurring PBDs have potent anticancer activity they have been precluded from clinical application due to side effects. In this report, we present a very efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepine analogues. The total synthesis of the subsituted benzyl DC-81s is completed in seven steps from 4-hydroxy-3-methoxybenzoic acid in 10-15% yields. The preliminary biological evaluation of these compounds will also be discussed. |
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New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |