(1R,2S,4S,5S,7S,9S,11S,13R)-13-chloro-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

• 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: (1R,2S,4S,5S,7S,9S,11S,13R)-13-chloro-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
• 化学式: C₂₀H₂₁ClO₆
• 分子量: 392.836
• InChiKey: NTVKGPDILFFEOC-COQXYOOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S,5S,7S,9S,11S,13R)-13-chloro-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 甲醇 、 sodium tetrahydroborate 作用下， 反应 1.0h， 以42%的产率得到Δ5,6-dehydrotriptolide
  参考文献：
  名称：

  Semisynthesis of triptolide analogues: Effect of B-ring substituents on cytotoxic activities

  摘要：

  A series of B-ring modified analogues of triptolide were synthesized and tested for their cytotoxicity against two human tumor cell lines (U251 and PC-3). From the current investigation, the structure-cytotoxic activity relationships of these analogues suggested that the introduction of hydroxyl, epoxide, halogen or olefinic groups on C5 and/or C6 could still retain the cytotoxicity, albeit a little less potency, and the C7,C8-beta-epoxide group of triptolide was essential to its potent cytotoxic activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.069
• 作为产物：
  描述：

  雷公藤内酯酮 在 N-氯代丁二酰亚胺 、 偶氮二异丁腈 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以62%的产率得到(1R,2S,4S,5S,7S,9S,11S,13R)-13-chloro-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
  参考文献：
  名称：

  Semisynthesis of triptolide analogues: Effect of B-ring substituents on cytotoxic activities

  摘要：

  A series of B-ring modified analogues of triptolide were synthesized and tested for their cytotoxicity against two human tumor cell lines (U251 and PC-3). From the current investigation, the structure-cytotoxic activity relationships of these analogues suggested that the introduction of hydroxyl, epoxide, halogen or olefinic groups on C5 and/or C6 could still retain the cytotoxicity, albeit a little less potency, and the C7,C8-beta-epoxide group of triptolide was essential to its potent cytotoxic activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.069

文献信息

• Semisynthesis of triptolide analogues: Effect of B-ring substituents on cytotoxic activities
  作者：Hongtao Xu、Yi Chen、Huanyu Tang、Huijin Feng、Yuanchao Li

  DOI：10.1016/j.bmcl.2014.10.069

  日期：2014.12

  A series of B-ring modified analogues of triptolide were synthesized and tested for their cytotoxicity against two human tumor cell lines (U251 and PC-3). From the current investigation, the structure-cytotoxic activity relationships of these analogues suggested that the introduction of hydroxyl, epoxide, halogen or olefinic groups on C5 and/or C6 could still retain the cytotoxicity, albeit a little less potency, and the C7,C8-beta-epoxide group of triptolide was essential to its potent cytotoxic activity. (C) 2014 Elsevier Ltd. All rights reserved.