15-hydroxyltriptolide | 99694-86-7

• 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: 15-hydroxyltriptolide
• 英文别名: triptolidenol；(1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-7-(2-hydroxypropan-2-yl)-1-methyl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one
• CAS: 99694-86-7
• 化学式: C₂₀H₂₄O₇
• 分子量: 376.406
• InChiKey: APBNDXHFQWSYOS-KSYZUNFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  15-hydroxyltriptolide 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以90%的产率得到15-hydroxytriptolide
  参考文献：
  名称：

  雷醇内酯衍生物及其应用

  摘要：

  本发明公开了雷醇内酯衍生物及其应用。具体而言，如通式(Ι)所示的化合物及其光学异构体和药学上可接受的盐；这类新的雷醇内酯衍生物的制备方法；含有这类雷醇内酯衍生物的药物组合物；以及这类雷醇内酯衍生物在制备抗肿瘤药物上的应用。

  公开号：

  CN104513290B
• 作为产物：
  描述：

  雷公藤甲素 在 Cunninghamella blakesleana 、 potato medium 作用下， 以 丙酮 为溶剂， 反应 120.0h， 以2%的产率得到15-hydroxyltriptolide
  参考文献：
  名称：

  Biotransformation of triptolide by Cunninghamella blakesleana

  摘要：

  Biotransformation of triptolide 1 by Cunninghamella blakesleana (AS 3.970) was carried out. Seven biotransformation products were obtained and four of them were characterized as new compounds. On the basis of their NMR and mass spectral data, their structures were characterized as 5alpha-hydroxytriptolide 2, 1beta-hydroxytriptolide 3, triptodiolide 4, 16-hydroxytriptolide 5, triptolidenol 6, 19alpha-hydroxytriptolide 7 and 19beta-hydroxytriptolide 8. All the new transformed products (2, 3, 7 and 8) were found to exhibit potent in vitro cytotoxicity against some human tumor cell lines. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00605-7

文献信息

• [EN] GLUCOSE CONJUGATES OF TRIPTOLIDE, ANALOGS AND USES THEREOF<br/>[FR] CONJUGUÉS GLUCOSE DE TRIPTOLIDE, ANALOGUES ET UTILISATIONS CORRESPONDANTS
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2017136739A1

  公开（公告）日：2017-08-10

  Provided are compounds generated by conjugation of triptolide with glucose to form glucose-triptolide conjugates, provides compounds with effective anti -proliferative activity and improved tolerability as compared to naturally occurring triptolide compounds.

  提供了由三尖杉酯与葡萄糖结合形成的葡萄糖-三尖杉酯共轭物，这些化合物具有有效的抗增殖活性，并且相比自然存在的三尖杉酯化合物具有更好的耐受性。
• Halogenated triptolide derivatives as immunomodulators and anticancer agents
  申请人：Dai Dongcheng

  公开号：US20050288364A1

  公开（公告）日：2005-12-29

  Compounds having the structure I: are useful for inducing cell death (apoptosis) and in immunosuppression. In structure I, CR 1 R 2 is selected from CHOH, C═O, CHF, CF 2 and C(CF 3 )OH; CR 6 and CR 13 are selected from CH, COH and CF; CR 7 R 8 , CR 9 R 10 and CR 11 R 12 are selected from CH 2 , CHOH, C═O, CHF and CF 2 ; and CR 3 R 4 R 5 is selected from CH 3 , CH 2 OH, C═O, COOH, CH 2 F, CHF 2 and CF 3 ; such that: at least one of R 1 -R 13 comprises fluorine; no more than two of CR 3 R 4 R 5 , CR 6 , CR 7 R 8 , CR 9 R 10 , CR 11 R 12 , and CR 13 comprises fluorine or oxygen; and, when CR 1 R 2 is CHOH, CR 3 R 4 R 5 is not CH 2 F.

  具有结构I的化合物对于诱导细胞死亡（凋亡）和免疫抑制具有用处。在结构I中，CR1R2从CHOH、C═O、CHF、CF2和C（CF3）OH中选择；CR6和CR13从CH、COH和CF中选择；CR7R8、CR9R10和CR11R12从CH2、CHOH、C═O、CHF和CF2中选择；CR3R4R5从CH3、CH2OH、C═O、COOH、CH2F、CHF2和CF3中选择；使得：R1-R13中至少有一个含氟；CR3R4R5、CR6、CR7R8、CR9R10、CR11R12和CR13中不超过两个含氟或氧；当CR1R2为CHOH时，CR3R4R5不是CH2F。
• Biotransformation of triptolide by Cunninghamella blakesleana
  作者：Lili Ning、Jixun Zhan、Guiqin Qu、Lei Zhong、Hongzhu Guo、Kaishun Bi、Dean Guo

  DOI：10.1016/s0040-4020(03)00605-7

  日期：2003.6

  Biotransformation of triptolide 1 by Cunninghamella blakesleana (AS 3.970) was carried out. Seven biotransformation products were obtained and four of them were characterized as new compounds. On the basis of their NMR and mass spectral data, their structures were characterized as 5alpha-hydroxytriptolide 2, 1beta-hydroxytriptolide 3, triptodiolide 4, 16-hydroxytriptolide 5, triptolidenol 6, 19alpha-hydroxytriptolide 7 and 19beta-hydroxytriptolide 8. All the new transformed products (2, 3, 7 and 8) were found to exhibit potent in vitro cytotoxicity against some human tumor cell lines. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 雷醇内酯衍生物及其应用
  申请人：中国医学科学院药物研究所

  公开号：CN104513290B

  公开（公告）日：2019-01-01

  本发明公开了雷醇内酯衍生物及其应用。具体而言，如通式(Ι)所示的化合物及其光学异构体和药学上可接受的盐；这类新的雷醇内酯衍生物的制备方法；含有这类雷醇内酯衍生物的药物组合物；以及这类雷醇内酯衍生物在制备抗肿瘤药物上的应用。