(3bR,9bS)-6-methoxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydro-2H-naphtho[2,1-e]isoindol-1-one | 1257268-11-3

• 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: (3bR,9bS)-6-methoxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydro-2H-naphtho[2,1-e]isoindol-1-one
• CAS: 1257268-11-3
• 化学式: C₂₁H₂₇NO₂
• 分子量: 325.451
• InChiKey: TXIKYJHAFQYXAR-GHTZIAJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3bR,9bS)-6-methoxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydro-2H-naphtho[2,1-e]isoindol-1-one 在 chromium(VI) oxide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以35%的产率得到(3bR,9bS)-6-methoxy-9b-methyl-7-propan-2-yl-2,3,3b,4,10,11-hexahydronaphtho[2,1-e]isoindole-1,5-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel triptolide analogues for anticancer activity

  摘要：

  Three types of novel triptolide analogues with 9,11-olefin (3-5), five-membered unsaturated lactam ring (6-7) or A/B cis ring junction (8-14) were synthesized. Although with 9,11-olefin instead of 9,11-beta-epoxide, compound 4a was much more active than the parent natural triptolide (1) with the lowest IC50 value of 0.05 nM for SKOV-3 cells, clearly challenging the traditional viewpoint on the necessity of 9,11-beta-epoxide group of triptolide. In addition, structure-activity relationships for three classes of compounds were studied. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.106
• 作为产物：
  描述：

  (3bR-反式)-3b,4,5,9b,10,11-六氢-6-甲氧基-9b-甲基-7-(1-甲基乙基)-菲并(1,2-c)呋喃-1(3H)-酮 在 氨 、 氯化铵 作用下， 以 水 为溶剂， 反应 48.0h， 以57%的产率得到(3bR,9bS)-6-methoxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydro-2H-naphtho[2,1-e]isoindol-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel triptolide analogues for anticancer activity

  摘要：

  Three types of novel triptolide analogues with 9,11-olefin (3-5), five-membered unsaturated lactam ring (6-7) or A/B cis ring junction (8-14) were synthesized. Although with 9,11-olefin instead of 9,11-beta-epoxide, compound 4a was much more active than the parent natural triptolide (1) with the lowest IC50 value of 0.05 nM for SKOV-3 cells, clearly challenging the traditional viewpoint on the necessity of 9,11-beta-epoxide group of triptolide. In addition, structure-activity relationships for three classes of compounds were studied. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.106