(1S,4S,6S,8R,10S,12R)-1-methyl-6-propan-2-yl-5,9-dioxa-15-azahexacyclo[10.7.0.02,8.04,6.08,10.013,17]nonadeca-2,13(17)-diene-7,16-dione | 1257268-06-6

• 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,12R)-1-methyl-6-propan-2-yl-5,9-dioxa-15-azahexacyclo[10.7.0.02,8.04,6.08,10.013,17]nonadeca-2,13(17)-diene-7,16-dione
• CAS: 1257268-06-6
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: KXJQPJYQFLWDPF-JZEYQUPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：
  71.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,4S,6S,8R,10S,12R)-1-methyl-6-propan-2-yl-5,9-dioxa-15-azahexacyclo[10.7.0.02,8.04,6.08,10.013,17]nonadeca-2,13(17)-diene-7,16-dione 在 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 10.0h， 以45%的产率得到(1S,2S,4S,5S,7S,9S,11S,13S)-1-methyl-7-propan-2-yl-3,6,10-trioxa-16-azaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-ene-8,17-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：

  在 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以65%的产率得到(1S,4S,6S,8R,10S,12R)-1-methyl-6-propan-2-yl-5,9-dioxa-15-azahexacyclo[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.