An expeditious and convergent synthesis of ailanthoidol

Rao, Maddali L. N.; Awasthi, Dheeraj K.; Banerjee, Debasis

doi:10.1016/j.tetlet.2010.02.018

Cited by 14 publications

(18 citation statements)

References 32 publications

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“…For example, initial debenzylation of 13 using TiCl 4 gave 18 in 89 % yield. This was then reduced using DIBAL‐H (diisobutylaluminium hydride) to give ailanthoidol ( 1 ) 1f. Hydrogenation (Pd/C) of benzofuran intermediates 14 and 15 gave the corresponding reduction products (i.e., 19 and 20 ) in quantitative yields.…”

Section: Resultsmentioning

confidence: 99%

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Challenges of “Going Nano”: Enhanced Electrochemical Performance of Cobalt Oxide Nanoparticles by Carbothermal Reduction and In Situ Carbon Coating

Bresser¹,

Paillard²,

Niehoff³

et al. 2014

ChemPhysChem

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The electrochemical performance of nano- and micron-sized Co(3)O(4) is investigated, highlighting the substantial influence of the specific surface area on the obtainable specific capacities as well as the cycling stability. In fact, Co(3)O(4) materials with a high surface area (i.e. a small particle size) show superior specific features, which are, however, accompanied by a rapid capacity fading, owing to the increased formation of an insulating polymeric surface film that results from transition-metal-catalyzed electrolyte decomposition. The simultaneous coating with carbon of Co(3)O(4) nanoparticles and in situ reduction of the Co(3)O(4) by a carbothermal route yields a CoO-Co-C nanocomposite. The formation of this material substantially enhances the long-term cycling stability and coulombic efficiency of the lithium-ion active material used. Although the metallic cobalt enhances the electronic conductivity within the electrode and remains electrochemically inactive (as revealed by in situ powder X-ray diffraction analysis), it might have a detrimental effect on the long-term cycling stability by catalytically inducing continuous electrolyte decomposition.

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Section: Resultsmentioning

confidence: 99%

“…Compound 1: 1a,1f Compound 18 (50 mg, 0.136 mmol) was dissolved in dry THF (10 mL) in a round‐bottomed flask (50 mL). DIBAL‐H (1 M solution in hexane; 0.543 mL, 0.543 mmol) was then added at –78 °C, and the mixture was stirred for 2 h at –78 °C.…”

Section: Methodsmentioning

confidence: 99%

Challenges of “Going Nano”: Enhanced Electrochemical Performance of Cobalt Oxide Nanoparticles by Carbothermal Reduction and In Situ Carbon Coating

Bresser¹,

Paillard²,

Niehoff³

et al. 2014

ChemPhysChem

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“…Ailanthoidol is a bioactive component isolated from Zanthoxylum ailanthoides and Salvia miltiorrhiza Bunge [2,13]. Our and other groups developed effective and simple methods to synthesis ailanthoidol [7,8,13], in light of the demonstrations that ailanthoidol has estrogenic [22], antitumor [4] and anti-inflammatory actions [3]. In addition, we constructed several ailanthoidol derivatives to investigate various pharmacological functions [13].…”

Section: Discussionmentioning

confidence: 99%

“…Ailanthoidol also exhibits several pharmacological effects that include inhibition of tumor promotion induced by 12- O -tetradecanoyl-phorbol-13-acetate [4], and prohibiting copper ion-mediated oxidation of low-density lipoprotein [5] and antimicrobial activity [6]. Various organic synthesis methods of ailanthoidol have been reported [3,7,8]. …”

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

Kim

Jun

Kim

2013

Korean J Physiol Pharmacol

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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.

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“…Natural 2-arylbenzofuran neolignans are an important class of organic compounds that have attracted much attention in medicinal chemistry for their various biological activities, including insecticidal, cytotoxic, anticomplement, antioxidant, and antimicrobial properties [11]. Consequently, many research groups have focused on total synthesis of plant-derived 2-arylbenzofurans, such as ailanthoidol and egonol isolated from Zanthoxylum ailanthoides [12,13] and Styrax japonicum [14,15], respectively. Benzophenanthridine alkaloids have been frequently found in the Zanthoxylum genus with a variety of structural modifications, either on the benzene rings of the benzophenanthridine skeleton or at the C-6 position [2,16].…”

mentioning

confidence: 99%

Antibacterial Benzofuran Neolignans and Benzophenanthridine Alkaloids from the Roots ofZanthoxylum capense

Luo¹,

Pedro²,

Milic³

et al. 2011

Planta Med

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An expeditious and convergent synthesis of ailanthoidol

Cited by 14 publications

References 32 publications

Challenges of “Going Nano”: Enhanced Electrochemical Performance of Cobalt Oxide Nanoparticles by Carbothermal Reduction and In Situ Carbon Coating

Challenges of “Going Nano”: Enhanced Electrochemical Performance of Cobalt Oxide Nanoparticles by Carbothermal Reduction and In Situ Carbon Coating

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

Antibacterial Benzofuran Neolignans and Benzophenanthridine Alkaloids from the Roots ofZanthoxylum capense

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