(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 | 1257268-24-8

• 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,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
• CAS: 1257268-24-8
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: KGCDYKSFCAAZLR-JXXFODFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (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 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 以90%的产率得到(1S,7S,9R,11S)-1-methyl-5-propan-2-yl-8,14-dioxapentacyclo[9.7.0.02,7.07,9.012,16]octadeca-2,4,12(16)-triene-6,15-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：

  (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