Yeh‐long Chen, Po-Hsu Chen, C. Chung
Mar 1, 2003
Citations
0
Influential Citations
7
Citations
Quality indicators
Journal
Helvetica Chimica Acta
Abstract
2-(Aryloxymethyl)-5-benzyloxy-1-methyl-1H-pyridin-4-ones 8a–8g, 2-(aryloxymethyl)-5-hydroxy-4H-pyran-4-ones 9a–9g, and 2-(aryloxymethyl)-5-hydroxy-1-methyl-1H-pyridin-4-ones 10a–10g were prepared from the known 5-benzyloxy-2-(hydroxymethyl)pyran-4-one (3) in a good overall yield. These compounds were evaluated in vitro against a three-cell lines panel consisting of MCF7 (breast), NCI-H460 (lung), and SF-268 (CNS), and the active compounds passed on for evaluation in the full panel of 60 human tumor cell lines derived from nine cancer cell types. The results indicated that 5-hydroxy derivatives are more favorable than their corresponding 5-benzyloxy precursors (10a–10gvs.8a–8g), and 1-methyl-1H-pyridin-4-ones are more favorable than their corresponding pyran-4(1H)-ones (10a–10gvs.9a–9g). Among these three types of compounds, 2-(aryloxymethyl)-5-hydroxy-1-methyl-1H-pyridin-4-ones 10a–10g were the most cytotoxic; they inhibited the growth of almost all the cancer cells tested. On the contrary, compound 8a (a mean GI50=27.8 μM), 8b (38.5), 8d (11.0), and 8e (30.5) are especially active against the growth of SK-MEL-5 (a melanoma cancer cell) with a GI50 of <0.01, 5.65, 0.55, and 0.03 μM, respectively (cf. Table 2).