ChemInform Abstract: Natural Product Chemistry. Part 153. Synthesis and Possible Anticancer Activity of 8-Nitronoracronycine

Since the strategy for the synthesis of 9-, 10- and 11-nitronoracronycine [3,4] could not be applied to the 8-nitronoracronycine 9, we here report the preparation of the latter by a fusion of methyl 2-amino-6-nitrobenzoate 2 and phloroglucinol 3. The fusion of 2 and 3 gave 1,3-dihydroxy-8-nitro-9(10H)-acridinone 6. Subsequent methylation, demethylation and reaction with 2-chloro-2-methyl-3-butyne afforded the desired 8-nitronoracronycine 9. Compound 9, 1,3-dimethoxy-10-methyl-8-nitro-9(10H)-acridinone 7 and 1,3-dihydroxy-10-methyl-8-nitro-9(10H)-acridinone 8 were tested by the National Cancer Institute (NCI) for possible anticancer activity.