Synthesis of 4- epi-Parviflorons A, C, and E: Structure-Activity Relationship Study of Antiproliferative Abietane Derivatives

The Journal of Organic Chemistry
Yui MiyajimaKyoko Nakagawa-Goto

Abstract

The first syntheses of 4- epi-parviflorons A, C, and E (4- epi-1-3) were achieved in 12-13 steps from commercially available (-)-abietic acid (5). All synthesized compounds, including intermediates and derivatives, were evaluated for antiproliferative activity against five human tumor cell lines. A structure-activity relationship study revealed no significant difference between Pf E and 4- epi-Pf E, the importance of two oxygen functional groups at C-11 and C-12 for antiproliferative activity, as well as a combination of carbomethoxy at C-4 and a benzoyl ester with electron-drawing group at C-12 or hydroxymethyl at C-4 and an appropriate oxidation state of ring-B/C for triple-negative breast cancer cell selectivity.

References

Mar 28, 2003·Bioorganic & Medicinal Chemistry·B GiganteM L Valdeira
Apr 20, 2010·Journal of Agricultural and Food Chemistry·Daniela TofaniAugusto Gambacorta
Feb 20, 2015·Journal of Medicinal Chemistry·Kyoko Nakagawa-GotoMasuo Goto
Sep 6, 2015·Archives of Gynecology and Obstetrics·Pankaj Kumar, Rupali Aggarwal
Oct 26, 2016·Bioorganic & Medicinal Chemistry·Kyoko Nakagawa-GotoMasuo Goto

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Citations

Nov 20, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Natalia A LuchnikovaIrina B Ivshina
Feb 24, 2021·Organic & Biomolecular Chemistry·Shintaro KawamuraMikiko Sodeoka
Aug 10, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Gurdeep SinghRamasamy Vijaya Anand

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