Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Total Synthesis and Anti-inflammatory Evaluation of Penchinone A and Its Structural Analogues

Total Synthesis and Anti-inflammatory Evaluation of Penchinone A and Its Structural Analogues
Yeon Jeong Jang, Young Hoon Jung, Hyung Sik Kim, Kyu Hyuck Chung, Mijin Jeon, Yongguk Oh, Suhkneung Pyo, Jong Hwan Kwak, In Su Kim
The 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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02212

DOI: 10.1021/acs.joc.7b02212

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