3β-hydroxy-17β-(1-ethanolamino)carbonyl-28-norlup-20(29)-ene

• 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: 3β-hydroxy-17β-(1-ethanolamino)carbonyl-28-norlup-20(29)-ene
• 英文别名: 3-hydroxy-N-(2-hydroxyethyl)lup-20(29)-en-28-amide；(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-N-(2-hydroxyethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxamide
• 化学式: C₃₂H₅₃NO₃
• 分子量: 499.778
• InChiKey: QPRRKHUHBAQZCI-BWXYOZBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  白桦脂酸 在 草酰氯 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 3β-hydroxy-17β-(1-ethanolamino)carbonyl-28-norlup-20(29)-ene
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Betulonic Acid Amides and Conjugates with Amino Acids

  摘要：

  Betulonic acid amides with aliphatic and heterocyclic amines and with L-amino acids were synthesized by the acid chloride method. Betulonic acid amide and L-methionine derivatives of betulonic acid and its 3-oxime effectively inhibit the influenza A virus. Betulonic acid octadecylamide is active against the herpes simplex type I virus. The conjugate of betulonic acid 3-oxime with L-methionine is also active toward HIV-1. The tested compounds mainly show no activity toward the ECHO6 virus, which is devoid of a coat.

  DOI：

  10.1023/b:rubi.0000015778.77887.f1

文献信息

• Structure−Activity Relationship Study of Betulinic Acid, A Novel and Selective TGR5 Agonist, and Its Synthetic Derivatives: Potential Impact in Diabetes
  作者：Cédric Genet、Axelle Strehle、Céline Schmidt、Geoffrey Boudjelal、Annelise Lobstein、Kristina Schoonjans、Michel Souchet、Johan Auwerx、Régis Saladin、Alain Wagner

  DOI：10.1021/jm900872z

  日期：2010.1.14

  protein-coupled receptor TGR5, known to be activated by bile acids and which mediates some important cell functions. This work revealed that betulinic (1), oleanolic (2), and ursolic acid (3) exhibited TGR5 agonist activity in a selective manner compared to bile acids, which also activated FXR, the nuclear bile acid receptor. The most potent natural triterpenoid betulinic acid was chosen as a reference

  我们在这里描述了针对G蛋白偶联受体TGR5的天然存在的三萜类化合物的生物筛选，已知该三肽类化合物被胆汁酸激活并介导了一些重要的细胞功能。这项工作揭示了白蛋白（1），齐墩果酸（2）和熊果酸（3）与胆汁酸相比，以选择性的方式表现出TGR5激动剂活性，胆汁酸也激活了核胆汁酸受体FXR。选择最有效的天然三萜类桦木酸作为SAR研究的参考化合物。在桦木酸支架上进行半合成，我们专注于C-3醇，C-17羧酸和C-20烯烃的结构修饰。特别地，在C-3位置附近的结构变化引起效力的重大改善，例如衍生物18 dia 2（RG-239）和19 dia 2。在体外和体内测试了最佳衍生物，并讨论了其生物学特性。