cis-(5R,6S)-5,6-dihydroxy-14-epitriptolide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: cis-(5R,6S)-5,6-dihydroxy-14-epitriptolide
• 英文别名: (1S,2S,4S,5S,7R,8S,9S,11S,12S,13R)-8,12,13-trihydroxy-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)-en-17-one
• 化学式: C₂₀H₂₄O₈
• 分子量: 392.406
• InChiKey: YCJUIWPDUYMFHW-YWBLBPQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5α-hydroxytriptonide 在 sodium tetrahydroborate 、 二甲氨基三氟化硫 、 硫酸 、 间氯过氧苯甲酸 、 copper(l) chloride 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 20.0h， 生成 cis-(5R,6S)-5,6-dihydroxytriptolide 、 cis-(5R,6S)-5,6-dihydroxy-14-epitriptolide
  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

• Triptolide Derivatives And Their Uses
  申请人：Li Yuanchao

  公开号：US20070197476A1

  公开（公告）日：2007-08-23

  The invention relates to triptolide derivatives of Formula (I), their pharmaceutically acceptable salts and optical isomers, Formula (I): wherein, C5 and C6 connect with each other by a C—C single bond or double bond; when C5 and C6 are connected with C—C single bond, X and Y represents independently hydrogen, oxygen, hydroxyl, halogen, lower alkyl-oxy, lower alkyl-amino, mercapto, lower alkyl-thio, the group of formula —OCOR, —OSO 2 R or —OPO(OH) 2 , each of which is attached to C5 and C6, R represents —(CH 2 )nCO 2 Na, —(CO 2 )nCO 2 K, or —(CH 2 )nCH 3 , wherein n=1-6; Z represents hydrogen, oxygen, hydroxyl, halogen, lower alkyl-oxy, lower alkyl-amino, mercapto, lower alkyl-thio, the group of formula —OCOR, —OSO 2 R or —OPO(OH)2, each of which is linked at C14-position, R represents —(CH2)nCO2Na, —(CO 2 )nCO 2 K, or —(CH 2 )nCH 2 , wherein n=1-6; wherein, the “_” linked with X, Y, and Z represents “ ” or “ ”, but X and Y cannot both be hydrogen atom at the same time, the methods for preparing them and their use as antiphlogistic agent, immunosuppressive agent or therapeutic agent for other related diseases.

  本发明涉及式（I）的三酰甲基衍生物、其药学上可接受的盐和光学异构体，式（I）如下： 其中，C5和C6通过C—C单键或双键连接；当C5和C6通过C—C单键连接时，X和Y分别表示氢、氧、羟基、卤素、较低的烷氧基、较低的烷基氨基、巯基、较低的烷硫基、式—OCOR、—OSO2R或—OPO（OH）2的基团，每个基团都连接在C5和C6上，其中R表示—（CH2）nCO2Na、—（CO2）nCO2K或—（CH2）nCH3，其中n为1-6；Z表示氢、氧、羟基、卤素、较低的烷氧基、较低的烷基氨基、巯基、较低的烷硫基、式—OCOR、—OSO2R或—OPO（OH）2的基团，每个基团都连接在C14位点，其中R表示—（CH2）nCO2Na、—（CO2）nCO2K或—（CH2）nCH2，其中n为1-6；其中，与X、Y和Z连接的“_”表示“”或“”，但X和Y不能同时为氢原子，本发明还涉及其制备方法以及作为抗炎剂、免疫抑制剂或治疗其他相关疾病的治疗剂的用途。
• 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.