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

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 s...

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Published inJournal of organic chemistry Vol. 84; no. 6; pp. 3239 - 3248
Main Authors Miyajima, Yui, Saito, Yohei, Takeya, Munehisa, Goto, Masuo, Nakagawa-Goto, Kyoko
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.03.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary: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.
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02832