(1S,4S,6S,8R,10S,12S)-1-methyl-6-propan-2-yl-5,9,15-trioxahexacyclo[10.7.0.02,8.04,6.08,10.013,17]nonadeca-2,13(17)-diene-7,16-dione | 1257644-04-4

• 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: (1S,4S,6S,8R,10S,12S)-1-methyl-6-propan-2-yl-5,9,15-trioxahexacyclo[10.7.0.02,8.04,6.08,10.013,17]nonadeca-2,13(17)-diene-7,16-dione
• CAS: 1257644-04-4
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: NDBFYINIVHOHLP-GSBAHSKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,4S,6S,8R,10S,12S)-1-methyl-6-propan-2-yl-5,9,15-trioxahexacyclo[10.7.0.02,8.04,6.08,10.013,17]nonadeca-2,13(17)-diene-7,16-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以95%的产率得到(1S,4S,6R,7R,8S,10S,12S)-7-hydroxy-1-methyl-6-propan-2-yl-5,9,15-trioxahexacyclo[10.7.0.02,8.04,6.08,10.013,17]nonadeca-2,13(17)-dien-16-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：

  (1S,2R,4R,5R,7R,9S,11S,13R)-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-ene-8,17-dione 在 叔丁基过氧化氢 、 四甲基氢氧化铵 作用下， 以 水 、 苯 为溶剂， 反应 5.0h， 以60%的产率得到(1S,4S,6S,8R,10S,12S)-1-methyl-6-propan-2-yl-5,9,15-trioxahexacyclo[10.7.0.02,8.04,6.08,10.013,17]nonadeca-2,13(17)-diene-7,16-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

• Synthesis and biological evaluation of novel triptolide analogues for anticancer activity
  作者：Bing Zhou、Zehong Miao、Gang Deng、Jian Ding、Yaxi Yang、Huijin Feng、Yuanchao Li

  DOI：10.1016/j.bmcl.2010.08.106

  日期：2010.11

  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.