Structural studies on bioactive compounds. 40.(1) Synthesis and biological properties of fluoro-, methoxyl-, and amino-substituted 3-phenyl-4H-1-benzopyran-4-ones and a comparison of their antitumor activities with the activities of related 2-phenylbenzothiazoles.

摘要: A new series of fluoro-, methoxyl-, and amino-substituted isoflavones have been synthesized as potential antitumor agents based on structural similarities to known flavones (quercetin genistein respectively) 2-phenylbenzothiazoles. Target compounds were using palladium-catalyzed coupling methodologies construct the central aryl carbon-carbon single bond. The isoflavone derivatives tested for in vitro activity human breast (MDA-MB-468 MCF-7) colon (HT29 HCT-116) cancer cell lines. Low micromolar GI50 values obtained a number cases, with MDA-MB-468 line being most sensitive overall. Notably, significant potentiation growth inhibitory (GI50<1 microM 12d, 12f, 12h, 12k, 12l, 12o but not methylene-bridged derivative 12i) was observed when cells co-incubated TBDD, powerful inducer cytochrome P450 (CYP)-1A1 activity, suggesting that can act substrates CYP1A1 bioactivation.