Sequential transformations of dipterocarpol (oximation, first-order Beckmann rearrangement, dehydration, isomerization) synthesized the new dammarane-type triterpenoid A-azepanodammara-20(21),24(25)-diene. Its cytotoxicity was studied in vitro against 60 cell lines of 9 human tumor types. The cytotoxicity against all cancer cell types increased significantly as compared to native dipterocarpol if an azepane fragment was introduced into ring A (percent inhibition from 15.72% to 82.08%). Detailed cytotoxicity studies confirmed the activity against a broad spectrum of human tumor cell lines with a mean (MID) log LC50 of 5.57.
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Acknowledgment
The work was performed on State Task Topic No. AAAA-A17-117011910023-2. We thank the National Cancer Institute for determining the in vitro antitumor activity of 1 and 3–5.
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Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2019, pp. 760–765.
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Smirnova, I.E., Petrova, A.V. & Kazakova, O.B. Synthesis and Cytotoxicity of A-Azepanodammaradiene. Chem Nat Compd 55, 883–889 (2019). https://doi.org/10.1007/s10600-019-02838-w
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DOI: https://doi.org/10.1007/s10600-019-02838-w