5α-hydroxytriptonide | 571176-87-9

• 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: 5α-hydroxytriptonide
• 英文别名: (5R)-5-hydroxytriptonide；5alpha-Hydroxytriptonide；(1S,2S,4S,5S,7S,9S,11S,13R)-13-hydroxy-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
• CAS: 571176-87-9
• 化学式: C₂₀H₂₂O₇
• 分子量: 374.39
• InChiKey: SVWZPKRMGJFEFO-COQXYOOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 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：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5α-hydroxytriptonide 在 二甲氨基三氟化硫 、 硫酸 、 间氯过氧苯甲酸 、 copper(l) chloride 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 19.0h， 生成 (1S,2S,4S,5S,7S,9S,11S,12S,13S)-12,13-dihydroxy-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
• 作为产物：
  描述：

  雷公藤内酯酮 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 5α-hydroxytriptonide
  参考文献：
  名称：

  （5R）-5-羟基雷公藤内酯醇的光学选择性工艺合成方法

  摘要：

  本发明涉及一种(5R)‑5‑羟基雷公藤内酯醇的光学选择性工艺合成方法，具体公开一种以雷公藤内酯酮(式II化合物)作为原料，经氧化、还原得到(5R)‑5‑羟基雷公藤内酯醇(式I化合物)纯品的方法。该方法原料来源简单且稳定、后处理操作简单、易于工业化。

  公开号：

  CN113754715B

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。
• Cytotoxic Biotransformed Products from Triptonide by<i>Aspergillus niger</i>
  作者：Ning, Lili、Qu, Guiqin、Ye, Min、Guo, Hongzhu、Bi, Kaishun、Guo, Dean

  DOI：10.1055/s-2003-43220

  日期：2003.9

  The diterpenoid triepoxides are the major active constituents of Tripterygium wilfordii with potent antitumor and immune activities. But the strong toxicity of these compounds has restricted their application to a great extent. In order to find more effective compounds with less toxicity, structural modifications of triptonide (1) by Aspergillus niger (AS 3.739) were investigated and four biotransformed products were obtained. Based on their chemical and spectral data, their structures were elucidated as 5α-hydroxytriptonide (2), triptolide (3), 17-hydroxytriptonide (4), and 16-hydroxytriptonide (5), among which 2, 4 and 5 are new compounds. All the three new transformed products showed cytotoxic activities against the majority of the human tumor cell lines tested, however, they are found to possess less cytotoxic activity when compared with 1. Both compounds 4 and 5 showed similar cytotoxic activity and their IC50 values were 5 - 15 fold less than 1, while 2 is about 100 times less active than 1.

  二萜三氧化物是威灵仙的主要活性成分，具有强大的抗肿瘤和免疫活性。但这些化合物的强烈毒性在很大程度上限制了它们的应用。为了找到毒性更小的有效化合物，研究人员研究了黑曲霉（AS 3.739）对三肽化物（1）的结构改造，并获得了四种生物转化产物。根据其化学和光谱数据，它们的结构被阐明为 5δ-羟基雷公藤内酯（2）、雷公藤内酯（3）、17-羟基雷公藤内酯（4）和 16-羟基雷公藤内酯（5），其中 2、4 和 5 为新化合物。这三种新的转化产物对大多数受测的人类肿瘤细胞株都显示出细胞毒性活性，但与 1 相比，它们的细胞毒性活性较低。化合物 4 和 5 显示出相似的细胞毒性活性，其 IC50 值比 1 低 5-15 倍，而 2 的活性比 1 低约 100 倍。
• US7626044B2
  申请人：——

  公开号：US7626044B2

  公开（公告）日：2009-12-01
• 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.
• （5R）-5-羟基雷公藤内酯醇的光学选择性工艺合成方法
  申请人：上海博璞诺科技发展有限公司

  公开号：CN113754715B

  公开（公告）日：2023-03-17

  本发明涉及一种(5R)‑5‑羟基雷公藤内酯醇的光学选择性工艺合成方法，具体公开一种以雷公藤内酯酮(式II化合物)作为原料，经氧化、还原得到(5R)‑5‑羟基雷公藤内酯醇(式I化合物)纯品的方法。该方法原料来源简单且稳定、后处理操作简单、易于工业化。