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- Title
Synthesis and Antitumor Activity Evaluation of γ-Monofluorinated and γ, γ-Difluorinated Goniothalamin Analogues.
- Authors
Yang, Yi; Yang, Zhenjun; Cheng, Chunru; Qing, Fengling
- Abstract
A series of novel γ, γ-difluorinated Goniothalamin analogues 4a- 4i and 6a- 6i were synthesized. The key steps included the construction of C-5 stereocenter adjacent to gem-difluoromethylene group by way of lipase AK catalyzed kinetic resolution, the introduction of aryl group via Stille coupling, and lactonization by 1,5-oxidative cyclization. These γ, γ-difluorinated Goniothalamin analogues 4a- 4i and their enantiomers 6a- 6i, together with several corresponding γ-monofluorinated Goniothalamin analogues were biologically evaluated against four different cancer cell lines. Compound 7h showed a nearly equivalent potency as the parent ( R)-Goniothalamin in the micromolar range. The different fluorine effects between fluoromethylene and gem-difluoromethylene on antitumor activity were discussed through the analysis of bioassay data.
- Subjects
LACTONE derivatives; STILLE reaction; FLUORINE; ANTINEOPLASTIC agents; DRUG resistance in cancer cells
- Publication
Chinese Journal of Chemistry, 2013, Vol 31, Issue 6, p805
- ISSN
1001-604X
- Publication type
Article
- DOI
10.1002/cjoc.201300227