Turtumic, an Asian spice, has long been used as an Ayurvedic medicine for the treatment of various ailments. Its major chemical component is curcumin, which was first isolated in 1815. Recently, the in vitro and in vivo studies indicated that curcumin has potential to prevent and treat various cancers, and the clinical study demonstrated that curcumin processes a high safety profile in human. The key obstacle for curcumin to advance to clinical use is its low bioavailability. The above-mentioned benefits and disadvantage of curcumin as a drug candidate triggered a large amount of research on searching for improved curcumin analogs for the potential clinical treatment of cancers. Recently, we have reported three scaffolds of curcumin analogs and identify that 1,5-diheteroaryl-1,4-diene-3-one is an optimum scaffold for development of curcumin-based anti-cancer agents. As part of our continuing curcumin project, the present study is to explore the effect of the size of the heteroaromic rings on the cytotoxicity of 1,5-diheteroaryl-1,4-diene-3-ones. Eleven new, bulky, N-containing heteroaromatic curcumin analogs have been designed and synthesized through the Horner-Wadsworth-Emmons reaction of 1,3-bis(diethylphosphonato)acetone with appropriate aromatic aldehydes. Each of our new analogs features two identical bulky heteroaromatic rings and a dienone linker. The cytotoxicity of these synthesized analogs towards an aggressive cervical cell line (HeLa) and a hormone-independent prostate cancer cell line (PC-3) has been evaluated. This poster will present the design, synthesis, and cytotoxic evaluation of these synthetic analogs inspired by curcumin.

1,5-Diheteroaryl-1,4-diene-3-ones: Promising, curcumin-inspired anticancer agents

248th National Meeting (2014)

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