Concise synthesis of licochalcone C and its regioisomer, licochalcone H

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• 作者：Zengtao Wang (1)
  Yongkai Cao (1)
  Suresh Paudel (1)
  Goo Yoon (2)
  Seung Hoon Cheon (1)
  
• 关键词：Licochalcone C ; Licochalcone H ; Acid ; mediated Claisen ; Schmidt condensation ; Total synthesis
• 刊名：Archives of Pharmacal Research
• 出版年：2013
• 出版时间：December 2013
• 年：2013
• 卷：36
• 期：12
• 页码：1432-1436
• 全文大小：
• 作者单位：Zengtao Wang (1)
  Yongkai Cao (1)
  Suresh Paudel (1)
  Goo Yoon (2)
  Seung Hoon Cheon (1)
  
  1. College of Pharmacy and Research Institute of Drug Development, Chonnam National University, Gwangju, 500-757, Korea
  2. College of Pharmacy, Mokpo National University, 1666 Youngsan-ro, Cheonggye-myeon, Muan-gun, Jeonnam, Korea
  
• ISSN：1976-3786

文摘

Licochalone C (7a) is a retrochalcone isolated from Glycyrrhiza inflata, which shows potent antioxidant properties and inhibition of bacterial growth and cellular respiration. Biological studies have suggested that licochalcone C attenuates the lipopolysaccharide and interferon-gamma induced inflammatory response by decreasing the expression and activity of inducible nitric oxide synthase and modulating the antioxidant network activity of superoxide dismutase, catalase, and glutathione peroxidase activity. Licochalcone C also inhibits NADH-cytochrome C reductase in the membrane fraction of Micrococcus luteus. Since pharmacological activity studies of licochalcone C are ongoing and the yield of the compound is poor from natural product, we report a concise four step synthesis of licochalcone C (7a) and its regioisomer, tentatively called licochalcone H (7b), by employing acid-mediated Claisen-Schmidt condensation as a key step with 6 and 20?% overall yield, respectively.