5-Cinnamoyl-6-aminouracil derivatives as novel anticancer agents. Synthesis, biological evaluation, and structure-activity relationships
- 31 March 1985
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 28 (4) , 497-502
- https://doi.org/10.1021/jm00382a020
Abstract
A biological evaluation in the series of 5-cinnamoyl-6-aminouracils was undertaken. These compounds were in an extended planar conformation fitting well with a possible stacking interaction between the nucleic bases of DNA; thus an eventual anticancer activity by intercalation could be hoped. 1,3-Dimethyl-5-cinnamoyl-6-aminouracil was active when administered i.p. against i.p.-implanted P388 leukemia in vivo [mouse] (percent T/C = 124). Two other compounds, 1,3-dimethyl-5-cinnamoyl-6-[(2-morpholinoethyl)amino]uracil and 1,3-dimethyl-5-cinnamoyl-6-[(2-piperidinoethyl)amino]uracil, bearing a hydrophilic side chain on the 6-amino group, exhibited cytoxic activity in vitro against L1210 leukemia. Structure-activity relationships were determined from these results and from studies of biological interactions with DNA.Keywords
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