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Oklahoma State University
OSU Research Week

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Synthesis of oxygen analogues of a promising anticancer drug

Synthesis of oxygen analogues of a promising anticancer drug

Field Watts


The thiochroman-based anticancer agent S-Het-A2 (NSC721689) has been shown to selectively induce apoptosis in cancer cells while leaving normal cells unharmed. This compound, however, possesses two metabolically reactive groups and exhibits relatively low oral bioavailability. In order to eliminate the reactive groups as well as improve solubility and potency, oxygen analogues of S-Het-A2, bearing less reactive functionality with similar donor/acceptor properties have been prepared in seven steps from phenol and 3,3-dimethylacryloyl chloride. Based upon the analogues prepared thus far, certain structural features appear to be important to its drug interaction with mortalin (HSPA9) in cancer cells. The poster will present synthesis and activity data for several analogues of SHet- A2 highlighting important substituent groups for optimal binding.