Journal of Heterocyclic Chemistry p. 1227 - 1232 (1996)
Update date:2022-08-03
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Morpholino Mannich bases of types 5, 12 react with tetronic acid in aqueous acetic acid to yield uncyclized lactones of types 7, 13. Acetylation and methylation of these products yields monoacetylmonomethyl derivatives which can then be cyclized in alkali to give unsaturated lactones of types 8, 16 and saturated lactones 9b, 15. The hydroxylactone 9a can be synthesized directly by reaction of 3,4,5-trimethoxybenzaldehyde with sesamol and tetronic acid in methanol. With few exceptions the lactones of type 8 and 16 have proven to be active inhibitors of tumor growth in the National Cancer Institute in vitro screening program against 60 diverse human cancer cell lines. The lactone 8 is particularly potent, inhibiting in vitro growth of some cancers at concentrations as low as 10-6-10-7 moles/l.
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