In our lab we synthesize an alcohol epoxide from substituted benzaldehydes and cyclohexanone (Figure 1). By varying the reactants, we are creating a library of compounds that we can use to further test their properties. To make the varying alcohol epoxide compounds we combined two solutions in a flow synthesis using an HPLC pump. Solution 1 contains benzaldehyde (or a similar substituted compound) and cyclohexanone (or a similar compound) dissolved in DMF. Solution 2 is made in a separate flask from sodium hydride and trimethylsulfoxonium iodide in DMF. We ran several combinations of reactants, exchanging the benzaldehyde, the cyclohexanone, or both in some cases through this process. Our goal in doing this is to create a library of compounds that can be tested using the Brine Shrimp Lethality Assay (BSLA). The BSLA is an assay used to test biological activity by finding an LC50 value, or the dose which is lethal to 50% of the brine shrimp. We use the BSLA as an initial indication of biological activity of our compounds. We will report the results of the syntheses and the LC50 values for several compounds.

Flow synthesis of an epoxide and brine shrimp lethality assay

255th National Meeting (2018)

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