Anti-ulcer effect of isoprenyl flavonoids. III. Synthesis and anti-ulcer activity of metabolites of 2'-carboxymethoxy-4,4'-bis(3-methyl-2-butenyloxy)chalcone.

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Abstract
Five dihydrochalcone derivatives, 2''-carboxymethoxy-4,4''-bis(3-methyl-2-butenyloxy)dihydrochalcone(M-6-b), 2''-4-bis(carboxymethoxy)-4''-(3-methyl-2-butenyloxy)dihydrochalcone(M-2), 2'',4-bis(carboxymethoxy)-4''-(3-carboxy-2-butenyloxy)dihydrochalcone(M-1-a), 2'',4-bis(carboxymethoxy)-4''-(3-hydroxymethyl-2-butenyloxy)dihydrochalcone(M-1-1b) and 2''-carboxymethoxy-4-hydroxy-4''-(3-methyl-2-butenyloxy)dihydrochalcone(M-4-b), which are the main metabolites in rats of a new anti-ulcer drug sofalcone (2''-carboxymethoxy-4,4''-bis(3-methyl-2-butenyloxy)chalcone) [an analog of Sophoradin, a constituent of Sophora subprostrata] were synthesized and the anti-ulcer activities of the major metabolites in humans, M-6-b, M-2, and M-1-a, were examined by Shay''s and Takagi''s methods and also by the use of rats with histamine-induced ulcer. The most active compound was M-6-b, which showed activity equal to or slightly weaker than that of sofalcone.

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