ethyl ent-16-hydroximinobeyeran-19-oate | 1143506-14-2

• 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: ethyl ent-16-hydroximinobeyeran-19-oate
• CAS: 1143506-14-2
• 化学式: C₂₂H₃₅NO₃
• 分子量: 361.525
• InChiKey: OMALUWGOWZYSCJ-RHSMJXSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  58.89
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl ent-16-hydroximinobeyeran-19-oate 在 氢气 作用下， 以 四氢呋喃 为溶剂， 50.0 ℃ 、303.99 kPa 条件下， 反应 5.0h， 生成 16-aminoisosteviol ethyl ester
  参考文献：
  名称：

  异雌甾醇骨架的新型脯氨酰胺为直接不对称醛醇缩合反应的有效有机催化剂

  摘要：

  在这项工作中，合成了两种具有异雌烯醇骨架的新脯氨酰胺，并将其用作不对称羟醛反应的手性催化剂。研究了溶剂效应，催化剂负载量，底物范围和水对反应的影响。仅在5mol％的负载下，合成的催化剂在室温下对环己酮和取代的苯甲醛的直接羟醛反应显示出优异的活性（高达98％的收率）和良好的立体选择性（高达87：13dr，90％ee）。

  DOI：

  10.2174/1570178615666171226163338
• 作为产物：
  描述：

  甜菊糖 在 硫酸 、 盐酸羟胺 、 碳酸氢钠 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 ethyl ent-16-hydroximinobeyeran-19-oate
  参考文献：
  名称：

  Synthesis, cytotoxic activity evaluation and HQSAR study of novel isosteviol derivatives as potential anticancer agents

  摘要：

  A series of novel isosteviol derivatives bearing amino alcohol and thiourea fragments have been stereo selectively synthesized and screened for their in vitro cytotoxic activities against three human cancer cell lines (HCT-116, HGC-27 and JEKO-1). The results demonstrated that these compounds exhibited prominent cytotoxicities. Especially, the compound Iw displayed the most potent anticancer activities against HCT-116 cell with IC50 value of 1.450 mu M. On the basis of this bioassay results, these derivatives were further investigated by the hologram quantitative structure activity relationship (HQSAR) technique. The optimal HQSAR model with q(2) = 0.663, r(2) = 0.895, SEE = 0.179 was generated using A/B/H/Ch as fragment distinction parameters and 4-7 as fragment size. This model was employed to predict the cytotoxic activities of test set compounds, and the predicted values were in good agreement with the experimental results. The contribution maps derived from the optimal model explained the individual atomic contribution to the total activity of single molecule. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.009

文献信息

• Synthesis, Cytotoxicity, and Leishmanicidal Evaluation of <i>Ent</i> ‐beyerene and <i>Ent</i> ‐kaurene Derivatives
  作者：Jilmar. A. Murillo、Fernando Echeverri、Winston Quinones、Fernando Torres、Laura Isaza、Sara M. Robledo、Tatiana Pineda、Horacio F. Olivo、Gustavo A. Escobar

  DOI：10.1002/ejoc.202001424

  日期：2021.6.21

  Synthesis of ent-beyerene and ent-kaurene derivatives of the sweetener Stevia is described, including the cytotoxicity tests and in vitro activity against Leishmania braziliensis, the most predominant form of the cutaneous leishmaniasis disease in America. Twenty-one of the 39 synthesized compounds showed high leishmanicidal activity, even at concentrations below 10 mM

  描述了甜味剂甜叶菊的ent- beyerene 和ent- kaurene 衍生物的合成，包括细胞毒性测试和对巴西利什曼原虫的体外活性，巴西利什曼原虫是美国皮肤利什曼病的最主要形式。39 种合成化合物中有 21 种显示出高杀利什曼原虫活性，即使浓度低于 10 mM
• 四环二萜化合物及制备和应用
  申请人：北京大学

  公开号：CN106543032B

  公开（公告）日：2018-05-01

  本发明属于药物化学、药理学与制剂领域，具体涉及四环二萜化合物、制备、药理作用机制研究、应用、制剂，涉及四环二萜化合物治疗抗凝血、脑缺血、脑中风、脑水肿、脑梗死、神经功能损伤的用途。
• Antileishmanial activity and cytotoxicity of ent-beyerene diterpenoids
  作者：Jilmar A. Murillo、Juan F. Gil、Yulieth A. Upegui、Adriana M. Restrepo、Sara M. Robledo、Winston Quiñones、Fernando Echeverri、Aurelio San Martin、Horacio F. Olivo、Gustavo Escobar

  DOI：10.1016/j.bmc.2018.11.030

  日期：2019.1

  We describe the in vitro activity of two natural isomeric ent-beyerene diterpenes, several derivatives and synthetic intermediates. Beyerenols 1 and 2 showed EC50 of 4.6 ± 9.4 and 5.3 ± 9.4 μg/mL against amastigotes of L. (V) brazilensis, with SI of 5.1 and 7.7, respectively. Beyerenol 1 was synthesized from stevioside. In vivo experiments with bereyenols showed cure in 50% of hamsters infected with

  我们描述了两种天然异构对映体-拜仁二萜，几种衍生物和合成中间体的体外活性。Beyerenols 1和2对巴西L.（V）的吻合动物的EC 50分别为4.6±9.4和5.3±9.4μg/ mL ，SI分别为5.1和7.7。从甜菊糖合成了苯二酚1。体内与bereyenols实验表明治愈感染仓鼠的50％L.（V）brazilensis局部施加如乳霜I（beyerenol 1，0.81％，重量/重量）和霜III（beyerenol 2，1.96％，w / w）。这些结果表明，通过局部应用，拜仁醇是皮肤利什曼病化学疗法的潜在候选者。巴西L.（V）变形虫的体外分析显示，EC中间体10和11的EC 50为1.1±0.1和1.3± 0.04μg / mL，SI分别为3.1和3.5 。
• 异甜菊醇衍生物及其应用
  申请人：上海海洋大学

  公开号：CN116375582A

  公开（公告）日：2023-07-04

  本发明公开了异甜菊醇衍生物及其应用，其通式结构如化学式1所示，其中R1为不同碳链长度的卤代烃或溴苄，R2为O、OH或NOH，R3为H或Br，具有PTP1B抑制活性，且抑制PTP1B酶活性的IC50为0.24μM，以异甜菊醇为原料经过化学修饰制备得到。本发明提供一类异甜菊醇衍生物，合成路线设计合理、原料易得，适于工业化应用，对PTP1B有显著的抑制活性和良好的选择性，可作为PTP1B抑制剂或选择性PTP1B抑制剂，在预防或治疗以PTP1B为靶点的Ⅱ型糖尿病或肥胖症等方面均有广泛的应用价值。
• Design, synthesis and cytotoxic evaluation of nitric oxide-releasing derivatives of isosteviol
  作者：Yan Liu、Tingting Wang、Yong Ling、Na Bao、Wei Shi、Li Chen、Jianbo Sun

  DOI：10.1111/cbdd.12956

  日期：2017.9

  Twenty‐six novel isosteviol derivatives coupled with two types of nitric oxide (NO) donors (furoxans and NONOates) were synthesized and screened for cytotoxic activities against four human cancer cell lines with sunitinib as the positive control. The results showed that seven furoxan‐based derivatives (8a, 8b, 8c, 8d, 8e, 9e, and 9f) exhibited desirable cytotoxic activities, while NONOate‐based derivatives displayed poor potency because of unstability. Compared with sunitinib, compounds 8a and 8e were more active on all tested cell lines, especially in HCT116 (8a, IC50 = 0.48 ± 0.02 μm; 8e, IC50 = 0.94 ± 0.01 μm); compounds 8b and 8d were more potent on HCT116 (IC50 = 3.39 ± 0.06 and 3.29 ± 0.03 μm), HepG2 (IC50 = 1.05 ± 0.03 and 5.37 ± 0.08 μm), and SW620 (IC50 = 1.33 ± 0.02 and 4.11 ± 0.05 μm) cell lines, and 8c exhibited higher activities on HepG2 cells with an IC50 = 4.76 ± 0.14 μm. NO‐releasing experiment of compounds 8a–e, 17a, 18a, 19a, and 21a reminded us that NO‐releasing amount of this series of isosteviol derivatives positively correlates with their cytotoxic activities.