(3aS,6aR,9aR,9bS,Z)-3-(2-fluorobenzylidene)-6,9-dimethylenedecahydroazuleno[4,5-b]furan-2(9bH)-one

• 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: (3aS,6aR,9aR,9bS,Z)-3-(2-fluorobenzylidene)-6,9-dimethylenedecahydroazuleno[4,5-b]furan-2(9bH)-one
• 英文别名: (3Z,3aS,6aR,9aR,9bS)-3-[(2-fluorophenyl)methylidene]-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• 化学式: C₂₁H₂₁FO₂
• 分子量: 324.395
• InChiKey: XICPPEYAYAGNSM-KWQGZDBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氟碘苯 、 去氢木香内酯 在 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以42%的产率得到(3aS,6aR,9aR,9bS,E)-3-(2-fluorobenzylidene)-6,9-dimethylenedecahydroazuleno[4,5-b]furan-2(9bH)-one
  参考文献：
  名称：

  The application of Heck reaction in the synthesis of guaianolide sesquiterpene lactones derivatives selectively inhibiting resistant acute leukemic cells

  摘要：

  A series of guaianolide-type sesquiterpene lactones derivatives with arylation of alpha-methylene-gamma-lactone moiety was synthesized using Heck reactions, and was evaluated for their activities against acute myelogenous leukemia (AML) cell line HL-60 and doxorubicin-resistant cell line HL-60/A. Although all compounds were significantly less active against HL-60 than the parent molecules, surprisingly, compounds 3a, 4c-4e, 5e, and 8d exhibited high potency against doxorubicin-resistant cell line HL-60/A (IC50 = 6.2-19 mu M), and their activities against HL-60/A were comparable to that of their parent molecules. In view of their novel activities against HL-60/A, compound 5e with inhibitory activity against HL-60/A (IC50 = 6.2 +/- 0.5 mu M) was selected for study its preliminary mechanism. The result reveals that compound 5e can obviously induce apoptosis. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.028

文献信息

• The application of Heck reaction in the synthesis of guaianolide sesquiterpene lactones derivatives selectively inhibiting resistant acute leukemic cells
  作者：Ya-Hui Ding、Hong-Xia Fan、Jing Long、Quan Zhang、Yue Chen

  DOI：10.1016/j.bmcl.2013.09.028

  日期：2013.11

  A series of guaianolide-type sesquiterpene lactones derivatives with arylation of alpha-methylene-gamma-lactone moiety was synthesized using Heck reactions, and was evaluated for their activities against acute myelogenous leukemia (AML) cell line HL-60 and doxorubicin-resistant cell line HL-60/A. Although all compounds were significantly less active against HL-60 than the parent molecules, surprisingly, compounds 3a, 4c-4e, 5e, and 8d exhibited high potency against doxorubicin-resistant cell line HL-60/A (IC50 = 6.2-19 mu M), and their activities against HL-60/A were comparable to that of their parent molecules. In view of their novel activities against HL-60/A, compound 5e with inhibitory activity against HL-60/A (IC50 = 6.2 +/- 0.5 mu M) was selected for study its preliminary mechanism. The result reveals that compound 5e can obviously induce apoptosis. (c) 2013 Elsevier Ltd. All rights reserved.