Ethynylbenzenoid metabolites of Antrodia camphorata: synthesis and inhibition of TNF expression

被引：18

作者：

Buccini, Marco ^{[1
]}

Punch, Kathryn A. ^{[1
]}

Kaskow, Belinda ^{[1
]}

Flematti, Gavin R. ^{[1
]}

Skelton, Brian W. ^{[2
]}

Abraham, Lawrence J. ^{[1
]}

Piggott, Matthew J. ^{[1
]}

机构：

[1] Univ Western Australia, Sch Chem & Biochem, Perth, WA 6009, Australia

[2] Univ Western Australia, Ctr Microscopy Characterisat & Anal, Perth, WA 6009, Australia

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 07期

关键词：

THALIDOMIDE ANALOGS; CARBONYL-COMPOUNDS; CYCLIZATION;

D O I：

10.1039/c3ob42333f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved synthesis of the anti-inflammatory natural product antrocamphin A (2), involving a key Castro-Stephens reaction, is presented, along with the first total synthesis of its congener antrocamphin B (3). Approaches towards the more complex co-metabolite antrodioxolanone (4) were unsuccessful, but a samarium diiodide-mediated pinacol coupling of antrocamphin B did provide the chiral epimers (51). Antrocamphin A (2) inhibits Tumour Necrosis Factor (TNF) reporter gene expression, but its development as an anti-inflammatory agent may be limited by cytotoxicity.

引用

页码：1100 / 1113

页数：14

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