seco-chiliolide lactone | 102904-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: seco-chiliolide lactone
• 英文别名: secochiliolide lactone；(4aR,4abeta,5R,5'S)-5'-(3-Furanyl)-4,4a,6,7,8,8a,4',5'-octahydro-6alpha-methyl-8abeta-(1-methylethenyl)spi；(4aR,5R,5'S,6R,8aS)-5'-(furan-3-yl)-6-methyl-8a-prop-1-en-2-ylspiro[3,4,4a,6,7,8-hexahydrochromene-5,3'-oxolane]-2,2'-dione
• CAS: 102904-57-4
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: LFYGUJGWDAXFFQ-JCRWAUQASA-N

物化性质

• 沸点：
  544.4±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  secochiliolide acid 在 N-溴代丁二酰亚胺(NBS) 、 sodium carbonate 、 盐酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 1.5h， 以30%的产率得到seco-chiliolide lactone
  参考文献：
  名称：

  Preparation and antitrypanosomal activity of secochiliolide acid derivatives

  摘要：

  Secochiliolide acid (1) isolated from the Patagonian shrub Nardophyllum biyoides, was used as a scaffold for the preparation of a series of nine derivatives. Compound 1 and its derivatives were tested against Trypanosoma cruzi epimastigotes grown in liquid media. It was first observed that secochiliolide acid (1) inhibited the proliferation of the parasites, with an IC50 of 2 mu g/mL. Six of the synthesized derivatives were also active with IC50's between 2 and 7 mu g/mL which are comparable to that of the commercial drug benznidazole (2.5 mu g/mL). These results indicate that the carboxyl group is not essential for the bioactivity of 1, while the presence of the tetrasubstituted exocyclic double bond seems to be important. Moreover, the presence of the furan and spirolactone rings is not essential for the bioactivity per se, but is important in combination with other structural fragments present in the molecule. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.064

文献信息

• Preparation and antitrypanosomal activity of secochiliolide acid derivatives
  作者：Gastón E. Siless、Esteban Lozano、Marianela Sánchez、Marcia Mazzuca、Miguel A. Sosa、Jorge A. Palermo

  DOI：10.1016/j.bmcl.2013.06.064

  日期：2013.9

  Secochiliolide acid (1) isolated from the Patagonian shrub Nardophyllum biyoides, was used as a scaffold for the preparation of a series of nine derivatives. Compound 1 and its derivatives were tested against Trypanosoma cruzi epimastigotes grown in liquid media. It was first observed that secochiliolide acid (1) inhibited the proliferation of the parasites, with an IC50 of 2 mu g/mL. Six of the synthesized derivatives were also active with IC50's between 2 and 7 mu g/mL which are comparable to that of the commercial drug benznidazole (2.5 mu g/mL). These results indicate that the carboxyl group is not essential for the bioactivity of 1, while the presence of the tetrasubstituted exocyclic double bond seems to be important. Moreover, the presence of the furan and spirolactone rings is not essential for the bioactivity per se, but is important in combination with other structural fragments present in the molecule. (C) 2013 Elsevier Ltd. All rights reserved.