pristimerol | 31654-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: pristimerol
• 英文别名: methyl (2R,4aS,6aS,6aS,14aS,14bR)-10,11-dihydroxy-2,4a,6a,6a,9,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1H-picene-2-carboxylate
• CAS: 31654-72-5
• 化学式: C₃₀H₄₂O₄
• 分子量: 466.661
• InChiKey: GAPWCQHXCIXKLV-WXPPGMDDSA-N

物化性质

• 熔点：
  241 °C
• 沸点：
  563.1±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pristimerol 在 potassium carbonate 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 16.0h， 生成 (9β,13α,14β,20α)-2-methoxy-3-hydroxy-9,13-dimethyl-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid
  参考文献：
  名称：

  SAR study of celastrol analogs targeting Nur77-mediated inflammatory pathway

  摘要：

  Nur77, an orphan member of the nuclear receptor superfamily, plays an important role in the regulation of inflammatory processes. Our previous work found that celastrol, a pentacyclic triterpene, bound to Nur77 to inhibit inflammation in a Nur77-dependent manner. Celastrol binding to Nur77 promotes Nur77 translocation from nucleus to cytoplasm, resulting in clearance of inflamed mitochondria and then alleviation of inflammation. Here, we report the design, synthesis, SAR study and biological evaluation of a series of celastrol analogs. A total of 24 celastrol derivatives were made. Compound 3a with a K-d of 0.87 mu M was found to be less toxic than celastrol and could be a hit molecule for further optimization. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.05.009
• 作为产物：
  描述：

  雷公藤红素 在 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 氘代甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 pristimerol
  参考文献：
  名称：

  SAR study of celastrol analogs targeting Nur77-mediated inflammatory pathway

  摘要：

  Nur77, an orphan member of the nuclear receptor superfamily, plays an important role in the regulation of inflammatory processes. Our previous work found that celastrol, a pentacyclic triterpene, bound to Nur77 to inhibit inflammation in a Nur77-dependent manner. Celastrol binding to Nur77 promotes Nur77 translocation from nucleus to cytoplasm, resulting in clearance of inflamed mitochondria and then alleviation of inflammation. Here, we report the design, synthesis, SAR study and biological evaluation of a series of celastrol analogs. A total of 24 celastrol derivatives were made. Compound 3a with a K-d of 0.87 mu M was found to be less toxic than celastrol and could be a hit molecule for further optimization. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.05.009

文献信息

• Structure of Pristimerin and Celastrol
  作者：Koji Nakanishi、Hiroshi Kakisawa、Yoshimasa Hirata

  DOI：10.1246/bcsj.29.7

  日期：1956.1

  Part structure (I) has been presented for pristimerin on grounds of chemical and spectroscopic evidences. Celastrol (tripterine) has been shown to be demetylated pristimerin, hence (I’).

  基于化学和光谱证据，已经提出了 pristimerin 的部分结构 (I)。Celastrol (tripterine) 已被证明是去甲基化的 pristimerin，因此 (I')。
• Structures of two new phenolic 24-nor-D:A-friedo-oleananes related to zeylasterone: A partial synthesis of trimethylzeylasterone
  作者：G.M.Kamal B. Gunaherath、A.A.Leslie Gunatilaka

  DOI：10.1016/s0040-4039(00)81834-1

  日期：1983.1

  Zeylasteral and desmethylzeylasterone, two new triterpenes from Kokoona zeylanica have been shown to be 2,3-dihydroxy-6,23-dioxo-24-nor-D:A-friedo-oleana-1,3,5(10),7-tetraen-29-oic acid methyl ester (20α) and 2,3-dihydroxy-6-oxo-24-nor-D:A-friedo-oleana-1,3,5(10),7-tetraen23,29-dioic acid (20α), respectively, and have been related to trimethylzeylasterone. A partial synthesis of trimethylzeylasterone starting

  Zekosteral和desmethylzeylasterone是来自Kokoona zeylanica的两个新的三萜，已被证明是2,3-dihydroxy-6,23-dioxo-24-nor-D：A-friedo-oleana-1,3,5（10），7- tetraen-29-oic acid甲酯（20α）和2,3-二羟基-6-oxo-24-nor-D：A-friedo-oleana-1,3,5（10），7-tetraen23,29-dioic酸（20α），分别与三甲基玉米甾酮有关。已经从普里斯汀开始部分合成三甲基玉米甾酮。
• The structure of zeylasterone - the first of a new series of phenolic 24-nor-D:A-friedo-oleanan triterpenes
  作者：G.M. Kamal、B. Gunaherath、A.A. Leslie Gunatilaka、M. Uvais、S. Sultanbawa、Mohamed I.M. Wazeer

  DOI：10.1016/0040-4039(80)88112-3

  日期：1980.1

  Zeylasterone, a new triterpene from Kokoona zeylanica, is shown to be 2,3-dihydroxy-6-oxo-24-nor-D:A-friedo-oleana-1,3,5(10),7-tetraen-23,29-dioic acid-29-methyl ester (20 α) (1), the first member of a new series of phenolic 24-nor-D:A-friedo-oleanans.

  Zeylasterone是来自Kokoona zeylanica的一种新的三萜，显示为2,3-二羟基-6-oxo-24-nor-D：A-friedo-oleana-1,3,5（10），7-tetraen-23， 29-二酸-29-甲酯（20α）（1），是新的一系列酚24-nor-D：A-弗里多-油酸酯类中的第一个成员。
• 807. Pristimerin. Part I. The nature of the chromophore
  作者：P. K. Grant、A. W. Johnson

  DOI：10.1039/jr9570004079

  日期：——
• Gunaherath, G. M. Kamal B.; Gunatilaka, A. A. Leslie, Journal of the Chemical Society. Perkin transactions I, 1983, # 12, p. 2845 - 2850
  作者：Gunaherath, G. M. Kamal B.、Gunatilaka, A. A. Leslie

  DOI：——

  日期：——