(18α,19β) 19,28-epoxy-2-nitro-olean-2-en-3-ol | 1415688-92-4

• 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: (18α,19β) 19,28-epoxy-2-nitro-olean-2-en-3-ol
• 英文别名: (18α,19β)-2-nitro-19,28-epoxyolean-2-en-3-ol；(1R,4R,5R,8R,13R,14R,17R,18R,19R)-4,5,9,9,13,20,20-heptamethyl-11-nitro-24-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracos-10-en-10-ol
• CAS: 1415688-92-4
• 化学式: C₃₀H₄₇NO₄
• 分子量: 485.707
• InChiKey: RBZNPGNXLDUWQQ-KCBLQPAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  35
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (18α,19β) 19,28-epoxy-2-nitro-olean-2-en-3-ol 在 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 133.0h， 生成 (18α,19β) diethyl 19,28-epoxy-2,3-seco-oleanane-2,3-dioate
  参考文献：
  名称：

  Simple structural modifications confer cytotoxicity to allobetulin

  摘要：

  A variety of allobetulin derivatives was synthesized from allobetulin or allobetulone. These compounds were screened for their cytotoxic activity using a photometric SRB assay employing six different human tumor cell lines. In summary, opening of ring A of allobetulin in general lowers the cytotoxicity, but the 2,3-seco diethyl ester was highly cytotoxic and remarkable selective for A549 lung carcinoma cells while being significantly less cytotoxic for non-malignant mouse fibroblasts. The introduction of an amino group at position C-3 in the allobetulin skeleton enhances cytotoxicity and furnishes highly cytotoxic compounds. Their selectivity to distinguish between cancer cell and non-malignant cell depends on the configuration at position C-3. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.015
• 作为产物：
  描述：

  白桦脂醇 在 硝酸 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 (18α,19β) 19,28-epoxy-2-nitro-olean-2-en-3-ol
  参考文献：
  名称：

  在位置2上取代的Lupane和18α-Oleanane衍生物，其细胞毒性和对癌细胞的影响

  摘要：

  在骨架的2位上含有负电取代基的Lupane衍生物通常具有细胞毒性，但是，最具活性的化合物选择性不够。为了进一步研究在Lupane和18α-油烷衍生物中2位取代基对其生物学特性的影响，我们制备了38种三萜类化合物，其中19种是新的，其中大多数在2位上被取代。我们获得了2-溴二氢丁二酸和2-溴代脲基乙二烯，它们的取代产生了在位置2具有各种取代基的衍生物，例如胺，酰胺，硫醇和硫醚。硝苯甲酮和二氢苯甲酸的硝化得到2-硝基和2，2-二硝基衍生物。十五个衍生物的IC 50 在化学敏感性CCRF-CEM（急性淋巴细胞白血病）细胞系上<50μM，并在另外7种癌细胞系（包括耐药性和2种非癌系）上进行了测试。2-氨基同素白蛋白的IC 50为4.6μM ，在S×处引起明显的肿瘤细胞阻滞，在G2 / M转变中略有改变，并在5×IC 50时强烈抑制DNA和RNA的合成。迄今为止，我们的研究小组制备的2-氨基异源白蛋

  DOI：

  10.1016/j.ejmech.2016.05.029

文献信息

• Preparation and nitration of allobetulin seco-derivatives
  作者：A. V. Shernyukov、Email: [e-mail]、I. Ya. Mainagashev、D. V. Korchagina、Yu. V. Gatilov、N. F. Salakhutdinov、G. A. Tolstikov

  DOI：10.1007/s10600-012-0392-0

  日期：2012.11

  2-Nitro-derivatives of allobetulone were prepared by reaction of allobetulin with nitric acid. 2β-Aminoallobetulin was synthesized by reduction of 2-nitrobetulone with LiAlH4. The corresponding allobetulin seco-derivatives were obtained via oxidation by H2O2 in the presence of K2CO3 of 2-nitroallobetulone and cleavage of 2,2-dinitroallobetulone by K2CO3 in H2O:THF.

  通过将全贝图醇与硝酸反应，制备了全贝图醇的2-硝基衍生物。通过用LiAlH4还原2-硝基贝图醇合成了2β-氨基全贝图醇。相关的全贝图醇分离衍生物是通过在K2CO3存在下用H2O2氧化2-硝基全贝图醇以及用K2CO3在水：THF中裂解2,2-二硝基全贝图醇获得的。
• Simple structural modifications confer cytotoxicity to allobetulin
  作者：Lucie Heller、Anja Obernauer、René Csuk

  DOI：10.1016/j.bmc.2015.05.015

  日期：2015.7

  A variety of allobetulin derivatives was synthesized from allobetulin or allobetulone. These compounds were screened for their cytotoxic activity using a photometric SRB assay employing six different human tumor cell lines. In summary, opening of ring A of allobetulin in general lowers the cytotoxicity, but the 2,3-seco diethyl ester was highly cytotoxic and remarkable selective for A549 lung carcinoma cells while being significantly less cytotoxic for non-malignant mouse fibroblasts. The introduction of an amino group at position C-3 in the allobetulin skeleton enhances cytotoxicity and furnishes highly cytotoxic compounds. Their selectivity to distinguish between cancer cell and non-malignant cell depends on the configuration at position C-3. (C) 2015 Elsevier Ltd. All rights reserved.
• Allobetulin derived seco-oleananedicarboxylates act as inhibitors of acetylcholinesterase
  作者：Lucie Heller、Stefan Schwarz、Anja Obernauer、René Csuk

  DOI：10.1016/j.bmcl.2015.04.086

  日期：2015.7

  Ring opening of allobetulone gave either seco-acid 8 or di-acid 4. These acids were converted into esters that were screened by Ellman's assay. A dibutenylester of low cytotoxicity (NIH 3T3 murine embryonic fibroblasts) was shown to be a good mixed-type inhibitor (K-i = 3.39, K-i' = 2.26 mu M) for acetylcholinesterase. (C) 2015 Elsevier Ltd. All rights reserved.
• Lupane and 18α-oleanane derivatives substituted in the position 2, their cytotoxicity and influence on cancer cells
  作者：Lucie Borkova、Sona Gurska、Petr Dzubak、Renata Burianova、Marian Hajduch、Jan Sarek、Igor Popa、Milan Urban

  DOI：10.1016/j.ejmech.2016.05.029

  日期：2016.10

  substituted in the position 2. From betulin, we obtained 2-bromo dihydrobetulonic acid and 2-bromo allobetulon and their substitutions yielded derivatives with various substituents in the position 2 such as amines, amides, thiols, and thioethers. Nitration of allobetulon and dihydrobetulonic acid gave 2-nitro and 2,2-dinitro derivatives. Fifteen derivatives had IC50 < 50 μM on a chemosensitive CCRF-CEM (acute

  在骨架的2位上含有负电取代基的Lupane衍生物通常具有细胞毒性，但是，最具活性的化合物选择性不够。为了进一步研究在Lupane和18α-油烷衍生物中2位取代基对其生物学特性的影响，我们制备了38种三萜类化合物，其中19种是新的，其中大多数在2位上被取代。我们获得了2-溴二氢丁二酸和2-溴代脲基乙二烯，它们的取代产生了在位置2具有各种取代基的衍生物，例如胺，酰胺，硫醇和硫醚。硝苯甲酮和二氢苯甲酸的硝化得到2-硝基和2，2-二硝基衍生物。十五个衍生物的IC 50 在化学敏感性CCRF-CEM（急性淋巴细胞白血病）细胞系上<50μM，并在另外7种癌细胞系（包括耐药性和2种非癌系）上进行了测试。2-氨基同素白蛋白的IC 50为4.6μM ，在S×处引起明显的肿瘤细胞阻滞，在G2 / M转变中略有改变，并在5×IC 50时强烈抑制DNA和RNA的合成。迄今为止，我们的研究小组制备的2-氨基异源白蛋