(3R,3aS,9R,9aS,9bS)-3-(azidomethyl)-9-hydroxy-6,9-dimethyl-3,3a,4,5,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one | 1403357-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,3aS,9R,9aS,9bS)-3-(azidomethyl)-9-hydroxy-6,9-dimethyl-3,3a,4,5,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• CAS: 1403357-79-8
• 化学式: C₁₅H₂₁N₃O₃
• 分子量: 291.35
• InChiKey: MGQFKMIQHACLPT-MJDBTJCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  parthenolide 在 叠氮基三甲基硅烷 、 三氟化硼乙醚 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.25h， 生成 (3R,3aS,9R,9aS,9bS)-3-(azidomethyl)-9-hydroxy-6,9-dimethyl-3,3a,4,5,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
  参考文献：
  名称：

  Guaianolide Sesquiterpene Lactones, a Source To Discover Agents That Selectively Inhibit Acute Myelogenous Leukemia Stem and Progenitor Cells

  摘要：

  Small molecules that can selectively target cancer stem cells (CSCs) remain rare currently and exhibit no common structural features. Here we report a series of guaianolide sesquiterpene lactones (GSLs) and their derivatives that can selectively eradicate acute myelogenous leukemia (AML) stem or progenitor cells. Natural GSL compounds arglabin, an anticancer clinical drug, and micheliolide (MCL), are able to reduce the proportion of AML stem cells (CD34(+)CD38(-)) in primary AML cells. Targeting of AML stem cells is further confirmed by a sharp reduction of colony-forming units of primary AML cells upon MCL treatment. Moreover, DMAMCL, the dimethylamino Michael adduct of MCL, slowly releases MCL in plasma and in vivo and demonstrates remarkable therapeutic efficacy in the nonobese diabetic/severe combined immunodeficiency AML models. These findings indicate that GSL is an ample source for chemical agents against AML stem or progenitor cells and that GSL is potentially highly useful to explore anti-CSC approaches.

  DOI：

  10.1021/jm301064b