A facil synthesis of benzophenanthridinium salts has been developed and used for preparing a number of these compounds. The antitumor activities in mouse leukemia L1210 (LE) and P388 (PS) were determined as well as some selected antimicrobial activities. Although antitumor activity was exhibited by several of the derivatives, none was as active as the naturally occurring alkaloid fagaronine. Fagaronine was made available as a synthetic by an improved procedure. Some structure-activity relationships among antitumor benzophenanthridinium salts are discussed.
A structural proof for fagaronine has been attained by synthesis. The sequence employed represents a new approach to the synthesis of such alkaloids by use of the Kessar benzyne cyclization. Various phenolic protecting groups were explored, of which the isopropoxy group was found to be most compatible with the overall synthetic scheme.Recently, an extremely active antileukemic alkaloid, fagaronine, was isolated1 from Fagara zanthoxyloides (Rutaceae). The structure of fagaronine was left somewhat in doubt, however, as spectral methods were insufficient to absolutely distinguish between la and lb, although la was suggested1 as the more likely structure.
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