(5bS,8S,8aR,9aS,9bS,10aR,10bS)-8-hydroxy-8a-isopropyl-10b-methyl-5,5b,6,8,8a,9a,9b,10b-octahydro-1H-bis(oxireno)[2',3':4b,5;2'',3'':6,7]phenanthro[1,2-c]furan-3(2H)-one

• 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: (5bS,8S,8aR,9aS,9bS,10aR,10bS)-8-hydroxy-8a-isopropyl-10b-methyl-5,5b,6,8,8a,9a,9b,10b-octahydro-1H-bis(oxireno)[2',3':4b,5;2'',3'':6,7]phenanthro[1,2-c]furan-3(2H)-one
• 英文别名: (1S,2R,4S,5S,7R,8S,12S)-8-hydroxy-1-methyl-7-propan-2-yl-3,6,15-trioxahexacyclo[10.7.0.02,4.02,9.05,7.013,17]nonadeca-9,13(17)-dien-16-one
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: IASDRLRGJUIZOE-MNSCTPAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5bS,8S,8aR,9aS,9bS,10aR,10bS)-8-hydroxy-8a-isopropyl-10b-methyl-5,5b,6,8,8a,9a,9b,10b-octahydro-1H-bis(oxireno)[2',3':4b,5;2'',3'':6,7]phenanthro[1,2-c]furan-3(2H)-one 在 selenium(IV) oxide 、 sodium phosphate dibasic dodecahydrate 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 120.0h， 生成 (5R)-5-羟基雷公藤内酯醇
  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：

  雷公藤甲素 在 4-二甲氨基吡啶 、 锂硼氢 、 氯化亚砜 、 三氟化硼乙醚 、 C.I.酸性橙108 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 (5bS,8S,8aR,9aS,9bS,10aR,10bS)-8-hydroxy-8a-isopropyl-10b-methyl-5,5b,6,8,8a,9a,9b,10b-octahydro-1H-bis(oxireno)[2',3':4b,5;2'',3'':6,7]phenanthro[1,2-c]furan-3(2H)-one
  参考文献：
  名称：

  一般转录因子TFIIH XPB亚基中的半胱氨酸残基的共价修饰通过转录抑制剂雷公藤内酯的单环氧化物切割。

  摘要：

  雷公藤甲素是传统中草药雷神藤的关键成分，具有有效的抗癌和免疫抑制作用。通过共价修饰XPB（一种通用转录因子TFIIH的亚基），它是一种不可逆的真核转录抑制剂。XPB的Cys342被鉴定为雷公藤内酯醇的12,13-环氧基团经过共价修饰的残基。XPB的Cys342突变为苏氨酸可赋予突变蛋白抗雷公藤甲素的能力。在HEK293T细胞系中用Cys342Thr突变体替代内源性野生型XPB，使其完全耐受雷公藤甲素，从而证实XPB是雷公藤内酯的生理相关靶标。一起，

  DOI：

  10.1002/anie.201408817

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.
• Covalent Modification of a Cysteine Residue in the XPB Subunit of the General Transcription Factor TFIIH Through Single Epoxide Cleavage of the Transcription Inhibitor Triptolide
  作者：Qing-Li He、Denis V. Titov、Jing Li、Minjia Tan、Zhaohui Ye、Yingming Zhao、Daniel Romo、Jun O. Liu

  DOI：10.1002/anie.201408817

  日期：2015.2.2

  Triptolide is a key component of the traditional Chinese medicinal plant Thunder God Vine and has potent anticancer and immunosuppressive activities. It is an irreversible inhibitor of eukaryotic transcription through covalent modification of XPB, a subunit of the general transcription factor TFIIH. Cys342 of XPB was identified as the residue that undergoes covalent modification by the 12,13‐epoxide

  雷公藤甲素是传统中草药雷神藤的关键成分，具有有效的抗癌和免疫抑制作用。通过共价修饰XPB（一种通用转录因子TFIIH的亚基），它是一种不可逆的真核转录抑制剂。XPB的Cys342被鉴定为雷公藤内酯醇的12,13-环氧基团经过共价修饰的残基。XPB的Cys342突变为苏氨酸可赋予突变蛋白抗雷公藤甲素的能力。在HEK293T细胞系中用Cys342Thr突变体替代内源性野生型XPB，使其完全耐受雷公藤甲素，从而证实XPB是雷公藤内酯的生理相关靶标。一起，