jo7b02212_si_001.pdf (1.31 MB)
Total Synthesis and Anti-inflammatory Evaluation of Penchinone A and Its Structural Analogues
journal contribution
posted on 2017-10-11, 00:00 authored by Yongguk Oh, Yeon Jeong Jang, Mijin Jeon, Hyung Sik Kim, Jong Hwan Kwak, Kyu Hyuck Chung, Suhkneung Pyo, Young Hoon Jung, In Su KimThe
first total synthesis and biological evaluation of penchinone
A and its structural analogues are described. The key steps for the
preparation of penchinone A derivatives involve the oxime-directed
palladium(II)-catalyzed oxidative acylation, Claisen rearrangement,
and base-mediated olefin migration. This transformation efficiently
provides a range of allyl-substituted biaryl ketones with site-selectivity
and functional group compatibility. In addition, all synthetic compounds
were screened for anti-inflammatory activity against nitric oxide
(NO), tumor necrosis factor alpha (TNF-α), and interleukin-6
(IL-6) with lipopolysaccharide (LPS)-induced RAW264.7 cells. Generally,
a range of penchinone A derivatives potently inhibited NO, TNF-α,
and IL-6 productions, compared to dexamethasone as a positive control.
Notably, penchinone A (8g) and its derivatives (8e and 8f) were found to exhibit anti-inflammatory
activity stronger than that of dexamethasone.
History
Usage metrics
Categories
Keywords
RAWLPSinterleukin -6base-mediated olefin migrationTotal Synthesisallyl-substituted biaryl ketonesStructural Analoguesdexamethasoneanti-inflammatory activityderivatives potentlyexhibit anti-inflammatory activityIL -6 productionsClaisen rearrangementgroup compatibilitypenchinoneAnti-inflammatory EvaluationTNFnitric oxide8 g8 f8 e
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC