(3bS,9bS)-6-hydroxy-7-isopropyl-9b-methyl-3b,4,10,11-tetrahydrophenanthro[1,2-c]furan-1,5(3H,9bH)-dione | 1257268-23-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3bS,9bS)-6-hydroxy-7-isopropyl-9b-methyl-3b,4,10,11-tetrahydrophenanthro[1,2-c]furan-1,5(3H,9bH)-dione
• 英文别名: (3bS,9bS)-6-hydroxy-9b-methyl-7-propan-2-yl-3b,4,10,11-tetrahydro-3H-naphtho[2,1-e][2]benzofuran-1,5-dione
• CAS: 1257268-23-7
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: MHZZHUMKOAYLPH-FOIQADDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3bS,9bS)-6-hydroxy-7-isopropyl-9b-methyl-3b,4,10,11-tetrahydrophenanthro[1,2-c]furan-1,5(3H,9bH)-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以82%的产率得到(3bS,5R,9bS)-5,6-dihydroxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e][2]benzofuran-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
• 作为产物：
  描述：

  cis-3,3b,4,9b,10,11-hexahydro-6-methoxy-9b-methyl-7-(-1-methylethyl)phenanthro<1,2-c>furan-1,5-dione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到(3bS,9bS)-6-hydroxy-7-isopropyl-9b-methyl-3b,4,10,11-tetrahydrophenanthro[1,2-c]furan-1,5(3H,9bH)-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

文献信息

• New facile enantio- and diastereo-selective syntheses of (−)-triptonide and (−)-triptolide
  作者：Hongrui Zhang、Haifeng Li、Jijun Xue、Rui Chen、Ying Li、Yu Tang、Chunxin Li

  DOI：10.1039/c3ob42183j

  日期：——

  A novel formal asymmetric synthesis of (−)-triptonide and (−)-triptolide, featuring a new alternative access to their known key intermediate 4, has been achieved through two synthetic routes in 9 steps with 13.6% total yield and 10 steps with 18.5% overall yield, respectively. This synthesis is scalable and hence has high potential for application to further synthetic elaboration and biologic investigation

  一种新颖的形式不对称合成（-）-雷公藤甲酰胺和（-）-雷公藤甲内酯的方法是，通过两种合成路线，分9步合成，总收率为13.6％，10步合成18.5，实现了对已知关键中间体4的新选择。总产率分别为％。这种合成是可扩展的，因此具有用于这种天然产物的进一步合成精细化和生物学研究的巨大潜力。