12,19-diacetoxy-15-hydroxy-16-norpimarane

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 12,19-diacetoxy-15-hydroxy-16-norpimarane
• 英文别名: [(1R,3S,4aS,4bR,7S,10aS)-3-acetyloxy-7-(hydroxymethyl)-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-1-yl]methyl acetate
• 化学式: C₂₃H₃₆O₅
• 分子量: 392.536
• InChiKey: GUWZMNOGGCIUGV-NENAYYCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  12,19-diacetoxy-15-hydroxy-16-norpimarane 在 甲基磺酰氯 、 三乙胺 作用下， 以36%的产率得到strobol C
  参考文献：
  名称：

  Semisynthesis of ent-norstrobane diterpenoids as potential inhibitor for factor Xa

  摘要：

  A semisynthesis of two ent-strobane diterpenoids strobols C (7) and D (14) was accomplished via a Wagnar-Meerwein rearrangement. Compounds 7, 14, and the intermediate products were evaluated for their inhibition on factor Xa (FXa). Among all the compounds screened for FXa inhibitory activity, three compounds 6, 7, and 9 showed significant inhibitory activities with IC50 values of 1067 +/- 164, 81 +/- 11, 1023 +/- 89 nM, respectively. The inhibitory activity on FXa described in this study highlight the importance of structural modification based on natural products in the development of FXa inhibitors.

  DOI：

  10.1016/j.bmcl.2018.05.036
• 作为产物：
  描述：

  奇壬醇 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 phosphomolybdic acid hydrate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 11.5h， 生成 12,19-diacetoxy-15-hydroxy-16-norpimarane
  参考文献：
  名称：

  Semisynthesis of ent-norstrobane diterpenoids as potential inhibitor for factor Xa

  摘要：

  A semisynthesis of two ent-strobane diterpenoids strobols C (7) and D (14) was accomplished via a Wagnar-Meerwein rearrangement. Compounds 7, 14, and the intermediate products were evaluated for their inhibition on factor Xa (FXa). Among all the compounds screened for FXa inhibitory activity, three compounds 6, 7, and 9 showed significant inhibitory activities with IC50 values of 1067 +/- 164, 81 +/- 11, 1023 +/- 89 nM, respectively. The inhibitory activity on FXa described in this study highlight the importance of structural modification based on natural products in the development of FXa inhibitors.

  DOI：

  10.1016/j.bmcl.2018.05.036

文献信息

• Semisynthesis of ent-norstrobane diterpenoids as potential inhibitor for factor Xa
  作者：Jianbin Wang、He Ma、Hongzheng Fu

  DOI：10.1016/j.bmcl.2018.05.036

  日期：2018.12

  A semisynthesis of two ent-strobane diterpenoids strobols C (7) and D (14) was accomplished via a Wagnar-Meerwein rearrangement. Compounds 7, 14, and the intermediate products were evaluated for their inhibition on factor Xa (FXa). Among all the compounds screened for FXa inhibitory activity, three compounds 6, 7, and 9 showed significant inhibitory activities with IC50 values of 1067 +/- 164, 81 +/- 11, 1023 +/- 89 nM, respectively. The inhibitory activity on FXa described in this study highlight the importance of structural modification based on natural products in the development of FXa inhibitors.