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Synthesis of 4- epi-Parviflorons A, C, and E: Structure-Activity Relationship Study of Antiproliferative Abietane Derivatives.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2019 Mar 15; Vol. 84 (6), pp. 3239-3248. Date of Electronic Publication: 2019 Mar 05. - Publication Year :
- 2019
-
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.
- Subjects :
- Abietanes chemical synthesis
Abietanes chemistry
Antineoplastic Agents chemical synthesis
Antineoplastic Agents chemistry
Cell Line, Tumor
Cell Proliferation drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Molecular Conformation
Structure-Activity Relationship
Abietanes pharmacology
Antineoplastic Agents pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 84
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 30793595
- Full Text :
- https://doi.org/10.1021/acs.joc.8b02832