The total syntheses of JBIR-94 and two synthetic analogs and their cytotoxicities against A549 (CCL-185) human small lung cancer cells

[Display omitted] •Cancer Research.•Small Molecule synthesis.•Organic Chemistry.•Medicinal Chemistry. 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...

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Veröffentlicht in:Tetrahedron letters 2020-01, Vol.61 (1), p.151360, Article 151360
Hauptverfasser: 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 L., Evans, Nicole, Beales, Joseph L., Christiansen, Michael A.
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Sprache:eng
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Zusammenfassung:[Display omitted] •Cancer Research.•Small Molecule synthesis.•Organic Chemistry.•Medicinal Chemistry. 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.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2019.151360