Ailanthoidol Derivatives and their Anti-inflammatory Effects

Jun

Korean J Physiol Pharmacol

2013

Self Cite

We reported that ailanthoidol, a neolignan from Zanthoxylum ailanthoides and Salvia miltiorrhiza Bunge, inhibited inflammatory reactions by macrophages and protected mice from endotoxin shock. We examined the anti-inflammatory activity of six synthetic ailanthoidol derivatives (compounds 1-6). Among them, compound 4, 2-(4-hydroxyphenyl)-5-(3-hydroxypropenyl)-7-methoxybenzofuran, had the lowest IC50 value concerning nitric oxide (NO) release from lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Compound 4 suppressed the generation of prostaglandin (PG) E2 and the expression of inducible NO synthase and cyclooxygenase (COX)-2 induced by LPS, and inhibited the release of LPS-induced pro-inflammatory cytokines from RAW264.7 cells. The underlying mechanism of compound 4 on anti-inflammatory action was correlated with the down-regulation of mitogen-activated protein kinase and activator protein-1 activation. Compound 4 is potentially an effective functional chemical candidate for the prevention of inflammatory diseases.

Section: Introductionmentioning

confidence: 99%

2-(4-Hydroxyphenyl)-5-(3-Hydroxypropenyl)-7-Methoxybenzofuran, a Novel Ailanthoidol Derivative, Exerts Anti-Inflammatory Effect through Downregulation of Mitogen-Activated Protein Kinase in Lipopolysaccharide-Treated RAW 264.7 Cells

Jun

Korean J Physiol Pharmacol

2013

Self Cite

First Synthesis and Anti‐Inflammatory Effects of Puerariafuran and its Derivatives

Yoon

Bulletin Korean Chem Soc

Jun

2015

The total synthesis of puerariafuran and its derivatives was achieved for the first time by the direct reaction between substituted α‐bromoacetophenones and resorcinol. The reaction was mediated by neutral alumina and was fully regio‐controlled. Subsequently, the Sonogashira coupling method was applied for puerariafuran preparation. Finally, the anti‐inflammatory effects of these prepared compounds were evaluated in lipopolysaccharide (LPS) stimulated RAW 264.7 macrophages. The results revealed that puerariafuran and its derivatives show weak inhibition activity on the production of inflammatory‐mediated nitric oxide.

Bulletin Korean Chem Soc

Integrated continuous‐flow/batch protocol for ortho‐selective alkynylation of (hetero)aryl tosylates

Lee

Song

et al. 2023

The ortho‐selective alkynylation of polyhalo‐substituted (hetero)aryl tosylates was investigated using an integrated continuous‐flow/batch protocol. Without the elimination of the tosyloxy group, the regioselective ortho‐metalation of the (hetero)aryl tosylates employing n‐BuLi and ZnCl2 was successfully achieved in continuous‐flow chemistry within 10.92 s (residence time). The Pd‐catalyzed Negishi alkynylations of various iodoethynyl (hetero)arenes and the resulting arylzinc species proceeded at room temperature in yields ranging from 51% to 95%. Finally, the synthetic utility of this strategy was validated by the synthesis of benzofuran and pyridofuran derivatives.