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Synthesis and structure-activity relationships of guaiane-type sesquiterpene lactone derivatives with respect to inhibiting NO production in lipopolysaccharide-induced RAW 264.7 macrophages.
Chen, Hao; Chen, Bing-Yang; Liu, Chun-Ting; Zhao, Zeng; Shao, Wen-Hao; Yuan, Hu; Bi, Kai-Jian; Liu, Jiang-Yun; Sun, Qing-Yan; Zhang, Wei-Dong.
Affiliation
  • Chen H; School of Pharmacy, Soochow University, Suzhou 215123, China; School of Pharmacy, Second Military Medical University, Shanghai 200433, China.
  • Chen BY; School of Pharmacy, Second Military Medical University, Shanghai 200433, China.
  • Liu CT; School of Pharmacy, Second Military Medical University, Shanghai 200433, China.
  • Zhao Z; School of Pharmacy, Second Military Medical University, Shanghai 200433, China.
  • Shao WH; School of Pharmacy, Second Military Medical University, Shanghai 200433, China.
  • Yuan H; School of Pharmacy, Second Military Medical University, Shanghai 200433, China; School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, China.
  • Bi KJ; School of Pharmacy, Second Military Medical University, Shanghai 200433, China.
  • Liu JY; School of Pharmacy, Soochow University, Suzhou 215123, China. Electronic address: liujiangyun@suda.edu.cn.
  • Sun QY; School of Pharmacy, Second Military Medical University, Shanghai 200433, China. Electronic address: sqy_2000@163.com.
  • Zhang WD; School of Pharmacy, Soochow University, Suzhou 215123, China; School of Pharmacy, Second Military Medical University, Shanghai 200433, China. Electronic address: wdzhangy@hotmail.com.
Eur J Med Chem ; 83: 307-16, 2014 Aug 18.
Article in En | MEDLINE | ID: mdl-24974350
A guaiane framework was scaffolded by photochemical rearrangement reactions using α-santonin 1 as a starting material. Then, using a series of reactions, we synthesized the guaiane-type sesquiterpene lactone 5 in high yield. The inhibitory activities of compound 5 and of a series of derivatives on nitric oxide (NO) release were evaluated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compounds 6g, 7h, 7i, 7k and 8g, exhibited significant inhibitory effects on NO production, with IC50 values of 14.8, 22.3, 18.3, 17.4 and 7.0 µM, respectively. Their cytotoxicities were also estimated using an MTT assay. The structure-activity relationships of these compounds were also discussed.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Lipopolysaccharides / Sesquiterpenes, Guaiane / Lactones / Macrophages / Nitric Oxide Limits: Animals Language: En Journal: Eur J Med Chem Year: 2014 Document type: Article Affiliation country: China Country of publication: France

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Lipopolysaccharides / Sesquiterpenes, Guaiane / Lactones / Macrophages / Nitric Oxide Limits: Animals Language: En Journal: Eur J Med Chem Year: 2014 Document type: Article Affiliation country: China Country of publication: France