19β,28-epoxy-2α-hydroxy-18α-oleanan-3-one | 106144-68-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 19β,28-epoxy-2α-hydroxy-18α-oleanan-3-one
• 英文别名: (1R,4R,5R,8R,11R,13R,14R,17R,18R,19R)-11-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracosan-10-one
• CAS: 106144-68-7
• 化学式: C₃₀H₄₈O₃
• 分子量: 456.709
• InChiKey: NSQAHWABWYYZEM-UGBXBDICSA-N

物化性质

• 沸点：
  542.7±25.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  33
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  19β,28-epoxy-2α-hydroxy-18α-oleanan-3-one 在 吗啉 、 sulfur 作用下， 反应 26.0h， 生成 allobetulone
  参考文献：
  名称：

  Reactions of triterpenoid ketones with sulfur and morpholine under the conditions of Willgerodt-Kindler reaction

  摘要：

  19β,28-环氧-18α-齐墩果烷-3-酮（I）在吗啡啉中加热与硫反应，生成2-酮衍生物II，伴随着少量的起始酮I。反应可以控制使得几乎只生成2-酮衍生物II。带有酮基和2、3位进一步官能团的衍生物III-VII也生成2-酮衍生物II。同样地，3-酮-18α-齐墩果烷-28→19β-酯（XVIII）被转化为2-酮衍生物XIX。1-酮衍生物VIII和A-去酮衍生物IX在这些条件下不发生反应。在反应混合物中加入邻二胺会导致形成带有吡嗪环与环A相接的化合物XIII、XV-XVII、XX。

  DOI：

  10.1135/cccc19860118
• 作为产物：
  描述：

  allobetulone 在 硫酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 19β,28-epoxy-2α-hydroxy-18α-oleanan-3-one
  参考文献：
  名称：

  用 DAST 氟化桦木碱和其他三萜类化合物

  摘要：

  Betulinines 是具有抗肿瘤活性的羽扇豆烷、des-E-羽扇豆烷、18-羽扇豆烯、20(29)-羽扇豆烯和 18α-齐墩果烷衍生物。我们使用二乙基氨基三氟化硫 (DAST) 作为氟化剂检查了这些衍生物的氟化。我们制备了 19β,28-epoxy-2,2-difluoro-18α-oleanan-3-one (3c), 19β,28-epoxy-2,2-di-fluoro-18α-oleanan-3β-ol (4a), 3β-acetoxy-30-fluorolup-20(29)-ene-28-oate (6b)、3β,28-diacetoxy-22-oxo-21,21-difluorolup-18-ene (8b) 和其他几种氟化桦木脑用于迄今为止未能证明显着抗癌活性的体外细胞毒性试验。

  DOI：

  10.1055/s-2005-861861

文献信息

• Reaction of lupane and oleanane triterpenoids with Lawesson's reagent
  作者：Miroslav Kvasnica、Iva Rudovska、Ivana Cisarova、Jan Sarek

  DOI：10.1016/j.tet.2008.02.023

  日期：2008.4

  The reactions of selected triterpenic oxo compounds with Lawesson's reagent were investigated. We examined sulfurization of some oxygen compounds and for these reactions several hindered ketones, one aldehyde, α-hydroxyketones, esters, or anhydrides were chosen. We synthesized 15 new sulfur derivatives, including thioketone 16, dimeric sulfides 17–19, and thiaderivatives 20–22. We also observed unusual

  研究了选定的三萜氧基化合物与Lawesson试剂的反应。我们检查了一些含氧化合物的硫化，对于这些反应，选择了几种受阻酮，一种醛，α-羟基酮，酯或酸酐。我们合成了15个新的硫衍生物，包括硫酮16，二聚硫化物17 - 19，和thiaderivatives 20 - 22。我们还观察到了不寻常的转化，提供了athathiaphosphinines 23a，23b和dithiaphospholanes 24。制备的化合物没有显示出任何明显的细胞毒性活性。
• Synthesis of cytotoxic 2,2-difluoroderivatives of dihydrobetulinic acid and allobetulin and study of their impact on cancer cells
  作者：Lucie Borkova、Lucie Jasikova、Jiri Rehulka、Katerina Frisonsova、Milan Urban、Ivo Frydrych、Igor Popa、Marian Hajduch、Niall J. Dickinson、Martin Vlk、Petr Dzubak、Jan Sarek

  DOI：10.1016/j.ejmech.2015.03.068

  日期：2015.5

  In this article, we describe the preparation and cytotoxic properties of a small focused library of lupane and 18 alpha-oleanane triterpenoids that contain a combination of two structural motifs known to enhance the biological activities. First, we introduced two fluorine atoms to position 2 of the skeleton. Second, we synthesized a set of hemiester prodrugs, which were intended to increase the solubility and activity. Starting from betulin, we obtained two hydroxyketones (derivatives of dihydrobetulinic acid and allobetulin) and their fluorination using DAST provided 2,2-difluoro-3-oxo-compounds as the main products. Then the 3-oxo group in each derivative was reduced by NaBH4 to obtain 3 beta-hydroxy compounds suitable for modifying by various hemiesters. We prepared 21 compounds, 11 of them new, their cytotoxicity was tested on T lymphoblastic leukemia CCRF-CEM cells first and the most active derivatives were selected for screening on another six tumor and two non-tumor cell lines. All of them showed selectivity against cancer lines with therapeutic index between 2 and 8. All hemiesters had activity in the same range as the free hydroxyl derivatives and they would be suitable prodrugs for future in vivo experiments. Interestingly, all hemiesters of 2,2-difluorodihydrobetulonic acid had higher activity against p53 knock-out p53-/- cancer cell line than against the non-mutated analog. In active derivatives, the cell cycle was analyzed by flow cytometry and several compounds slowed down cell cycle progression through G0/G1 or S-phase. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Klinot, Jiri; Sejbal, Jan; Vystrcil, Alois, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 2, p. 400 - 412
  作者：Klinot, Jiri、Sejbal, Jan、Vystrcil, Alois

  DOI：——

  日期：——
• Sejbal, Jan; Klinot, Jiri; Vystrcil, Alois, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 4, p. 1052 - 1061
  作者：Sejbal, Jan、Klinot, Jiri、Vystrcil, Alois

  DOI：——

  日期：——
• TRITERPENOID DERIVATIVES AND THEIR USE AS ANTIPROLIFERATIVE AGENTS
  申请人：Univerzita palackeho V Olomouci

  公开号：EP1289977A2

  公开（公告）日：2003-03-12