(3S,5R,6S,10R)-3-(furan-3-yl)-6-(2-isocyanatoethyl)-10-methyl-7-propan-2-ylidene-2-oxaspiro[4.5]decan-1-one | 1449750-57-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,5R,6S,10R)-3-(furan-3-yl)-6-(2-isocyanatoethyl)-10-methyl-7-propan-2-ylidene-2-oxaspiro[4.5]decan-1-one
• CAS: 1449750-57-5
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: MOYRHUROTBULRZ-QBMUGXQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,5R,6S,10R)-3-(furan-3-yl)-6-(2-isocyanatoethyl)-10-methyl-7-propan-2-ylidene-2-oxaspiro[4.5]decan-1-one 在 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 以21.3 mg的产率得到1,3-bis[2-[(3S,5R,6S,10R)-3-(furan-3-yl)-10-methyl-1-oxo-7-propan-2-ylidene-2-oxaspiro[4.5]decan-6-yl]ethyl]urea
  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
• 作为产物：
  描述：

  secochiliolide acid 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (3S,5R,6S,10R)-3-(furan-3-yl)-6-(2-isocyanatoethyl)-10-methyl-7-propan-2-ylidene-2-oxaspiro[4.5]decan-1-one
  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.