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The Total Syntheses of JBIR-94 and Two Synthetic Analogs and Their Cytotoxicities Against A549 (CCL-185) Human Small Lung Cancer Cells

Mangum, Cathy L., Munford, Mica B., Sam, Alyssa B., Young, Sandra K., Beales, Jeremy T., Subedi, Yagya Prasad, Mangum, Chad D., Allen, Tanner J., Liddell, Miranda S., Merrell, Andrew I., Saavedra, Diana I., Williams, Becky J., Evans, Nicole, Beales, Joseph L., Christiansen, Michael A.
Tetrahedron letters 2019
chemical reactions, chemical structure, cytotoxicity, free radical scavengers, humans, inhibitory concentration 50, lung neoplasms, neoplasm cells, polyphenols
We here disclose the total syntheses of the natural polyphenol JBIR-94 and two nonnatural analogs, whose structures are of interest for their bioactivity potential as radical scavengers. Although we initially attempted this by dually acylating both of putrecine’s amine nitrogens in a single pot, our endeavors with this method (which has been successfully reported by other groups) proved ineffectual. We accordingly opted for the lengthier approach of acylating each amine individually, which gratuitously prevailed and also aligns with separate literature precedent. Moreover, we here share our analysis of these target compounds’ cytotoxicities and IC50 values against A549 (CCL-185) human small lung cancer cells.