Coumarins are naturally occurring oxygen heterocyclic compounds having multifarious medicinal properties, hence used as lead compounds for designing new potent analogs. The chromene butenoic acid 3 and the benzochromene butenoic acid 4 which are derived from the reaction of glyoxalic acid with 3-acetylcoumarin and 3-acetylbenzocoumarin, respectively, were reacted with different nitrogen and carbon nucleophiles to give new heterocyclic compounds. The structures of the prepared compounds were

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... idated by IR, 1 H-NMR, and mass spectroscopy. Some of the newly prepared compounds were tested in vitro against a panel of four human tumor cell lines namely; hepatocellular carcinoma (liver) HepG2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. Also they were tested as antioxidants. Almost all of the tested compounds showed satisfactory activity. The hormone oestrogen plays the crucial role in the development of the breast cancer, the most frequent malignant disease in women. Therefore many therapies are designed to block its activity [27] . Cinnamoyl-coumarin derivatives were especially effective in oestrogen-dependent cancers, such as breast (MCF7) and ovarian (OVCAR) cancer cell lines. These compounds are selective nonsteroidal inhibitors of 14β-hydroxysteroid dehydrogenase type 1, an enzyme that catalyzes NADPH-dependent reduction of the weak oestrogen, oestrone, into the most potent oestrogen, oestradiol [28] . Seidel et al. [29] synthesized a series of coumarin derivatives which carry α,β-(monoor bis)-unsaturated ketones at the C3 or C4 position such as compound I (Figure 1 ) which strongly inhibits proliferation in the chronic myeloid leukemia K-562 and histiocytic lymphoma U-937 cell lines. This compound also inhibited the activity of histone deacetylase (HDAC), an enzyme crucial in cancer development.