N-(2-aminoethyl)-3β-hydroxy-11-oxo-olean-12-en-30-amide | 912541-99-2

• 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: N-(2-aminoethyl)-3β-hydroxy-11-oxo-olean-12-en-30-amide
• 英文别名: N-(2-aminoethyl)glycyrrhetinamide；(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-N-(2-aminoethyl)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxamide
• CAS: 912541-99-2
• 化学式: C₃₂H₅₂N₂O₃
• 分子量: 512.776
• InChiKey: HFRQHSFQIRQETC-XWEVEMRCSA-N

物化性质

• 熔点：
  193-199 °C (decomp)
• 沸点：
  657.6±55.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-aminoethyl)-3β-hydroxy-11-oxo-olean-12-en-30-amide 在 copper(II) sulfate 1H-咪唑-1-磺酰叠氮盐酸盐 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以73%的产率得到(2S,4aS,6aS,6bR,10S,12aS)-N-(2-azidoethyl)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxamide
  参考文献：
  名称：

  [EN] 18-BETA-GLYCYRRHETINIC ACID DERIVATIVES WITH ANTI-TUMOR ACTIVITY
  [FR] DÉRIVÉS D'ACIDE 18?-GLYCYRRHÉTINIQUE AYANT UNE ACTIVITÉ ANTITUMORALE

  摘要：

  这项发明涉及医学和美容领域，更准确地说是抗癌治疗、炎症性疾病和糖尿病治疗以及抗衰老或抗皱剂领域，使用新合成的18β-甘草酸衍生物及其在治疗上述疾病或症状中的应用。

  公开号：

  WO2012022780A1
• 作为产物：
  描述：

  N-[2-(tert-butoxycarbonylamino)ethyl]glycyrrhetinamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以65%的产率得到N-(2-aminoethyl)-3β-hydroxy-11-oxo-olean-12-en-30-amide
  参考文献：
  名称：

  [ 11 C]光气用于放射性合成N-（2- {3- [3,5-双（三氟甲基）]苯基[ 11 C]脲基}乙基）甘草次乙酰胺，它是肿瘤中蛋白酶体和激酶的抑制剂

  摘要：

  据报道，N-（2- {3- [3,5-双（三氟甲基）]苯基脲基}乙基）甘草次酸酰胺（2）是脲基取代的甘草次酸的衍生物（1），具有对蛋白酶体和蛋白酶体的有效抑制活性。激酶，在肿瘤中过表达。在这项研究中，我们使用[ 11 C]光气（[ 11 C] COCl 2）作为标记剂标记了这种不对称尿素2，期望[ 11 C] 2可以成为正体发射层析成像配体，用于蛋白酶体和核糖体的成像。肿瘤中的激酶。[ 11 C] 2的放射合成策略使3,5-双（三氟甲基）苯胺的盐酸盐（4 ·HCl）与[ 11 C] COCl 2反应，可能生成异氰酸酯[ 11 C] 6，然后使[ 11 C] 6与N-（ 2-氨基乙基）甘草次酸酰胺（3）。

  DOI：

  10.1016/j.bmcl.2012.04.049

文献信息

• 一种肝靶向阿霉素/Bcl-2 siRNA共载纳米胶 束及其制备方法和应用
  申请人：潍坊医学院

  公开号：CN109481400B

  公开（公告）日：2021-03-16

  本发明提供了一种载药纳米胶束及其制备方法和应用，该载药纳米胶束其包含药物和/或基因、DPP聚合物和甘草次酸修饰的透明质酸聚合物，所述DPP聚合物具有式(I)所示结构：式(I)其中，n为≥13的自然数。本发明的载药纳米胶束采用了新的聚合物载体DPP，并引入了GH聚合物，提高了药物递送的靶向性，尤其肝靶向性、降低了摄取速率、提高了抗癌效果。本发明的聚合物及载药纳米胶束也可用于制备其他基因与疏水性药物联用的肝靶向递送体系。
• 靶向调控线粒体能量代谢的化合物及其应用和药物
  申请人：四川大学

  公开号：CN111848717A

  公开（公告）日：2020-10-30

  本发明公开了靶向调控线粒体能量代谢的化合物及其应用和药物，药物领域。本发明公开的化合物具有如下结构式：本发明首次发现，该化合物可靶向调控线粒体能量代谢，可用于治疗线粒体能量代谢依赖的疾病，该化合物原料来源于天然植物，具有资源丰富、安全性高等优点，在线粒体能量代谢异常的相关疾病的治疗中具有潜在的应用前景，为此类疾病的治疗提供了新的策略。
• 一种靶向聚合物制备方法、靶向脂质体、脂质 体靶向制剂的制备方法及应用
  申请人：潍坊医学院

  公开号：CN109364024B

  公开（公告）日：2020-11-06

  本发明公开了一种靶标分子二硬脂酰基磷脂酰乙醇胺‑聚乙二醇‑甘草次酸，利用靶标分子制备脂质体，该脂质体包括以下组分DSPE‑PEG‑GA、卵磷脂和胆固醇，由于GA分子的引入使得脂质体递送药物的准确性提高，运送药物到达靶标部位进行释放，更好的发挥抗肿瘤作用，故利用该脂质体负载CUR与CA4P，得到CUR&CA4P/GA‑LPs。本发明采用姜黄素和康普瑞汀磷酸二钠两种药物联合，通过抑制肿瘤细胞增殖和抗肿瘤血管生成两种途径达到协同抗肿瘤的效果，并解决了单一药物长期治疗所产生的肿瘤耐药性问题。
• Amino derivatives of glycyrrhetinic acid as potential inhibitors of cholinesterases
  作者：Stefan Schwarz、Susana Dias Lucas、Sven Sommerwerk、René Csuk

  DOI：10.1016/j.bmc.2014.04.046

  日期：2014.7

  The development of remedies against the Alzheimer's disease (AD) is one of the biggest challenges in medicinal chemistry nowadays. Although not completely understood, there are several strategies fighting this disease or at least bringing some relief. During the progress of AD, the level of acetylcholine (ACh) decreases; hence, a therapy using inhibitors should be of some benefit to the patients. Drugs presently used for the treatment of AD inhibit the two ACh controlling enzymes, acetylcholinesterase as well as butyrylcholinesterase; hence, the design of selective inhibitors is called for. Glycyrrhetinic acid seems to be an interesting starting point for the development of selective inhibitors. Although its glycon, glycyrrhetinic acid is known for being an AChE activator, several derivatives, altered in position C-3 and C-30, exhibited remarkable inhibition constants in micro-molar range. Furthermore, five representative compounds were subjected to three more enzyme assays (on carbonic anhydrase II, papain and the lipase from Candida antarctica) to gain information about the selectivity of the compounds in comparison to other enzymes. In addition, photometric sulforhodamine B assays using murine embryonic fibroblasts (NiH 3T3) were performed to study the cytotoxicity of these compounds. Two derivatives, bearing either a 1,3-diaminopropyl or a 1H-benzotriazolyl residue, showed a BChE selective inhibition in the single-digit micro-molar range without being cytotoxic up to 30 mu M. In silica molecular docking studies on the active sites of AChE and BChE were performed to gain a molecular insight into the mode of action of these compounds and to explain the pronounced selectivity for BChE. (C) 2014 Elsevier Ltd. All rights reserved.
• <i>N</i>-(2-{3-[3,5-Bis(trifluoromethyl)phenyl]ureido}ethyl)-glycyrrhetinamide (<b>6b</b>): A Novel Anticancer Glycyrrhetinic Acid Derivative that Targets the Proteasome and Displays Anti-Kinase Activity
  作者：Benjamin Lallemand、Fabien Chaix、Marina Bury、Céline Bruyère、Jean Ghostin、Jean-Paul Becker、Cédric Delporte、Michel Gelbcke、Véronique Mathieu、Jacques Dubois、Martine Prévost、Ivan Jabin、Robert Kiss

  DOI：10.1021/jm200285z

  日期：2011.10.13

  18-beta-Glycyrrhetinic acid (GA; 1) and many of its derivatives are cytotoxic in cancer cells. The current study aims to characterize the anticancer effects of 17 novel 1 derivatives. On the basis of these studies, N-(2-3-[3,5-bis(trifluoromethyl)phenyl]ureido}ethyl)-glycyrrhetinamide (6b) appeared to be the most potent compound, with IC50 in vitro growth inhibitory concentrations in single-digit micromolarity in a panel of 8 cancer cell lines. Compound 6b is cytostatic and displays similar efficiency in apoptosis-sensitive versus apoptosis-resistant cancer cell lines through, at least partly, the inhibition of the activity of a cluster of a dozen kinases that are implicated in cancer cell proliferation and in the control of the actin cytoskeleton organization. Compound 6b also inhibits the activity of the 3 proteolytic units of the proteasome. Compound 6b thus represents an interesting hit from which future compounds could be derived to improve chemotherapeutic regimens that aim to combat cancers associated with poor prognoses.