3beta-羟基-20-氧代-30-去甲羽扇豆-28-酸甲酯 | 4356-32-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 3beta-羟基-20-氧代-30-去甲羽扇豆-28-酸甲酯
• 中文别名: 己二酸盐氢2-乙基己基
• 英文名称: methyl (3β)-3-hydroxy-20-oxo-30-norlupan-28-oate
• 英文别名: Methyl 3beta-hydroxy-20-oxo-30-norlupan-28-oate；methyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• CAS: 4356-32-5
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: ZHIVKEAQDLRABF-FZFNOLFKSA-N

物化性质

• 沸点：
  539.2±25.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3beta-羟基-20-氧代-30-去甲羽扇豆-28-酸甲酯 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以97%的产率得到methyl 3,20-dioxo-30-norlupan-28-oate
  参考文献：
  名称：

  Incorporation of a Michael acceptor enhances the antitumor activity of triterpenoic acids

  摘要：

  Finding and developing drugs for the treatment of cancer has been challenging scientists for many decades, and using compounds of natural origin represents one of several strategies. Triterpenoic acids are a very promising class of secondary metabolites being able to induce apoptosis while their cytotoxicity is low. Therefore, derivatizations have to be conducted to improve cytotoxicity while retaining their ability to induce programmed cell death. The incorporation of a Michael acceptor into molecules resulted very often in drugs of improved cytotoxicity. Thus, in this study we synthesized and evaluated several Michael acceptor substituted compounds derived from glycyrrhetinic, ursolic, oleanolic and platanic acid. The influence of the presence of such a functional group onto the cytotoxicity was investigated in calorimetric sulforhodamine B assays employing several human cancer cell lines. EC50 values in the single-digit micromolar range were measured. Thus, the incorporation of a Michael acceptor unit into triterpenoic acids enhances the cytotoxicity of these compounds significantly. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.004
• 作为产物：
  描述：

  白桦脂酸 在 臭氧 作用下， 以 乙醚 、 氯仿 为溶剂， 生成 3beta-羟基-20-氧代-30-去甲羽扇豆-28-酸甲酯
  参考文献：
  名称：

  来自 Leptospermum scoparium 的三种羽扇豆衍生物

  摘要：

  Leptospermum scoparium 栽培品种地上部分的乙醚提取物产生具有 20,29,30-trinorlupane 骨架的内酯 (1)。此外，分离出 2α-羟基熊果酸 (2)、铂酸 (3) 和 3β, 30-二羟基-lup-20 (29)-烯-28-油酸 (4)。

  DOI：

  10.1002/ardp.19963291005

文献信息

• [EN] COMPOUNDS FOR REDUCING GLUCOCORTICOIDS, AND METHODS OF TREATMENT THEREOF<br/>[FR] COMPOSÉS PERMETTANT DE RÉDUIRE LES GLUCOCORTICOÏDES, ET PROCÉDÉS DE TRAITEMENT ASSOCIÉS
  申请人：BIONICHE LIFE SCIENCES INC

  公开号：WO2014071506A1

  公开（公告）日：2014-05-15

  A method for reducing glucocorticoids in an animal in need thereof comprising the use of compounds of the formula (I), wherein the definitions for R', R1-R11 and n are as disclosed in the description. The compounds of formula (I) are for the treatment or prevention of a glucocorticoid-related disorder for maintaining bone density, maintaining and improving the immune system, treating Cushing' s syndrome, treating obesity, improving reproduction efficiency, treating metabolic disorder, treating hypertension, treating hyperglycemia, treating insulin resistance, treating type 2 diabetes, and/or aiding in cancer and immune therapies

  一种用于减少需要动物体内糖皮质激素的方法，包括使用式(I)的化合物，其中R'、R1-R11和n的定义如描述中所披露。式(I)的化合物用于治疗或预防与糖皮质激素相关的疾病，以维持骨密度、维护和改善免疫系统、治疗库欣综合征、治疗肥胖、提高生殖效率、治疗代谢紊乱、治疗高血压、治疗高血糖、治疗胰岛素抵抗、治疗2型糖尿病，和/或在癌症和免疫疗法中发挥作用。
• Platanic acid-derived methyl 20-amino-30-norlupan-28-oates are potent cytotoxic agents acting by apoptosis
  作者：Michael Kahnt、Lucie Heller、Ahmed Al-Harrasi、Renate Schäfer、Ralph Kluge、Christoph Wagner、Choijiljav Otgonbayar、René Csuk

  DOI：10.1007/s00044-018-2189-6

  日期：2018.7

  derivatives of betulinic acid (2) and 12 derivatives of platanic acid (3) has been prepared and screened for their cytotoxic activity using SRB assays. First synthetic approaches were focused on the preparation of augustic acid (4) analogs of 2 and 3 by introducing a second hydroxyl group on the A-ring of both triterpenoic acids leading to compounds 5–14. Further structural modifications were performed at

  制备了一组八种桦木酸衍生物（2）和十二烷酸衍生物（3），并使用SRB分析筛选了它们的细胞毒性活性。第一种合成方法的重点是通过在两个三萜酸的A环上引入第二个羟基，从而生成化合物5 – 14，来制备2和3的奥古斯特酸（4）类似物。进一步的结构修改，通过其在转化的C-20酮基的铂酸骨架的进行成肟部分和随后还原成20-氨基-30-norlupan衍生物17 - 24。在SRB分析中，低EC观察到50个值，尤其是（3β，20  R）-3-乙酰氧基-20-氨基-30-去甲甲pan-28-酸酯（21），甲基（3β，20  S）-3-乙酰氧基-20-氨基-30的值。 -norlupan-28-oate（22）和（3β，20  R）-3,28-diacetyloxy-20-amino-30-norlupane（24）都在C-20上具有氨基功能。选择化合物21进行广泛的生物学测试，结果表明该化合物通过诱导细胞凋亡导致细胞死亡。
• The chemistry of triterpenes and related compounds. Part XLVI. Some novel products from the ozonolysis of methyl acetylbetulinate
  作者：R. T. Aplin、Rosalind P. K. Chan、T. G. Halsall

  DOI：10.1039/j39690002322

  日期：——

  Ozonolysis of methyl acetylbetulinate (II) gives number of products in addition to the nor-ketone (V) formed by the normal fission of the isopropenyl double-bond. They include the Baeyer–Villiger oxidation product (VIII) of the nor-ketone and two trisnor-compounds. In one of these (XVIII) the isopropenyl group has been lost and a Δ18,19 double-bond has been formed at the carbon to which it was attached

  除通过异丙烯基双键的正常裂变形成的正酮（V）外，对乙酰基乙酸丁二酸甲酯（II）进行臭氧分解还可得到多种产品。它们包括正酮的Baeyer-Villiger氧化产物（VIII）和两个trisnor化合物。在这些（XVIII）之一中，异丙烯基已经丢失，并且在其所连接的碳上形成了Δ18,19双键。在另一个（XI）中，异丙烯基已被氢取代。讨论了形成这些产物的可能机理。
• Platanic acid: A new scaffold for the synthesis of cytotoxic agents
  作者：Michael Kahnt、Lucie Heller、Patricia Grabandt、Ahmed Al-Harrasi、René Csuk

  DOI：10.1016/j.ejmech.2017.11.046

  日期：2018.1

  Thirty-seven different derivatives (2-38) have been prepared from platanic acid, a natural occurring triterpenoid. Main emphasis was the introduction of several N-containing functional groups such as amines, amides and oximes and their screening for cytotoxic activity employing several human tumor cell lines using SRB assays. In these SRB assays, nearly all compounds showed good cytotoxicity for these

  三十七个不同衍生物（2 - 38）已经从铂酸，天然存在的三萜类化合物制备。主要重点是引入几种含N的官能团（例如胺，酰胺和肟），并利用几种人肿瘤细胞系使用SRB分析法筛选其细胞毒性活性。在这些SRB分析中，几乎所有化合物都对这些人类肿瘤细胞系显示出良好的细胞毒性。然而，将两种化合物（17和38）提交了扩展的生物学测试，并使用荧光显微镜和FACS分析对其作用方式进行了研究。化合物17，甲基（3β，20 R）3-乙酰氧基-20-氨基-30-去甲鲁班-28-油酸酯诱导A2780卵巢癌细胞凋亡。
• Zur Kenntnis der Triterpene. (56. Mitteilung). Zur Oxydation des Betulin-monoacetats und des Acetyl-betulinsäure-methylesters mit Chromtrioxyd
  作者：L. Ruzicka、A. H. Lamberton

  DOI：10.1002/hlca.194002301157

  日期：——