benzyl ent-16-oxobeyeran-19-oate | 1266676-06-5

• 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: benzyl ent-16-oxobeyeran-19-oate
• 英文别名: benzyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate；16-oxo-beyerane-19-acid benzyl ester；benzyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 1266676-06-5
• 化学式: C₂₇H₃₆O₃
• 分子量: 408.581
• InChiKey: HOQJPWDEPMKPSG-FIVJYGDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl ent-16-oxobeyeran-19-oate 在 吡啶 、 selenium(IV) oxide 、 palladium 10% on activated carbon 、 盐酸羟胺 、 氢气 、 乙酸酐 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 73.0h， 生成
  参考文献：
  名称：

  Design, synthesis and cytotoxic evaluation of nitric oxide-releasing derivatives of isosteviol

  摘要：

  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.

  DOI：

  10.1111/cbdd.12956
• 作为产物：
  描述：

  stevioside 在 氢溴酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.5h， 生成 benzyl ent-16-oxobeyeran-19-oate
  参考文献：
  名称：

  作为新型心脏保护剂的异甜菊醇衍生物的合成和体内筛选

  摘要：

  异甜菊醇是一种 ent-beyerane 二萜，已多次被报道具有有效的心脏保护活性。为了从异甜菊醇中发现新的心脏保护衍生物，使用易于处理且高效的斑马鱼模型在体内合成和评估了47 种化合物，其中包括 40 种新化合物。因此讨论了这类化合物的构效关系。在这些化合物中，新衍生物15d在体内表现出最显着的功效。我们的结果表明，15d可以有效地防止多柔比星引起的斑马鱼形态畸变和心脏功能障碍。在斑马鱼模型中，其心脏保护活性远优于异甜菊醇和左西孟旦。H9c2细胞的分子机制表明，15d通过抑制活性氧过量产生、恢复线粒体膜电位和维持线粒体形态来保护心肌细胞死亡和损伤。因此，15d作为潜在的心脏保护临床试验候选药物值得进一步开发。本研究是将合成、构效关系研究和体内研究相结合的成功范例。 筛选以有效地从异甜菊醇中发现新的心脏保护剂。

  DOI：

  10.1016/j.ejmech.2021.113396

文献信息

• Isosteviol derivatives as protein tyrosine Phosphatase-1B inhibitors: Synthesis, biological evaluation and molecular docking
  作者：Na Li、Xinyu Li、Meidi Deng、Feifei Zhu、Zian Wang、Ruilong Sheng、Wenhui Wu、Ruihua Guo

  DOI：10.1016/j.bmc.2023.117240

  日期：2023.4

  a series of isosteviol derivatives 1–28 was synthesized and the inhibitory activity on PTP1B was evaluated by double antibody sandwich ELISA (DAS-ELISA) in vitro. Most isosteviol derivatives showed moderate PTP1B inhibitory activities. Among them, derivatives 10, 13, 24, 27 showed remarkable bioactivities with IC50 values ranging from 0.24 to 0.40 µM. Particularly, derivative 24 exhibited the best inhibitory

  蛋白酪氨酸磷酸酶 (PTP1B) 拮抗胰岛素信号传导，并作为与肥胖和 II 型糖尿病相关的胰岛素抵抗的潜在治疗靶点。在这项工作中，合成了一系列异甜菊醇衍生物1-28 ，并通过体外双抗体夹心 ELISA (DAS-ELISA) 评估了对 PTP1B 的抑制活性。大多数异甜菊醇衍生物显示出中等的 PTP1B 抑制活性。其中，衍生物10、13、24、27具有显着的生物活性， IC 50值在0.24-0.40 μM之间。特别地，衍生物24对 PTP1B 表现出最好的抑制活性（IC50  = 0.24 µM)体外; 此外，它对 PTP1B 的选择性比T细胞蛋白酪氨酸磷酸酶 (TCPTP)高 7 倍，对 PTP1B 的选择性比细胞分裂周期 25 同系物 B (CDC25B) 高 14 倍。分子对接研究表明 PTP1B 中24和 LYS-116 残基之间的氢键相互作用可能对抑制活性至关重要。结果表明，衍
• Synthesis and biological evaluation of novel exo-methylene cyclopentanone tetracyclic diterpenoids as antitumor agents
  作者：Jing Li、Dayong Zhang、Xiaoming Wu

  DOI：10.1016/j.bmcl.2010.11.055

  日期：2011.1

  The structure of exo-methylene cyclopentanone, which exists in nature tetracyclic diterpenoids products, has been proved to be an innate group for the treatment of cancer and inflammation. In this letter, four different scaffolds of tetracyclic diterpenoids including the structure exo-methylene cyclopentanone were synthesized from steviol and isosteviol and evaluated in vitro for their antitumor activity against three human cancer lines. Compounds 1a, 1b, 2b and 3b showed significant cytotoxicity, particularly, tetracyclic diterpenoids 2b, 3b were identified as the most potent and selective anticancer agents superior to adriamycin with IC50 values of 0.9 mu M and 1.5 mu M, against Hep-G2 and MDA-MB-231 cell lines, respectively. (C) 2010 Elsevier Ltd. All rights reserved.