heterobetulin | 508-81-6

• 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: heterobetulin
• 英文别名: 3β,28-Dihydroxy-18α,19βH-urs-20-en；(4aR)-10c-Hydroxy-1t.2.6at.6bc.9.9.12ac-heptamethyl-4ar-hydroxymethyl-(8atH.12btH.14acH.14btH)-Δ²-eicosahydro-picen；Taraxasten-(20)-diol-(3β.28)；18α.19βH-Ursen-(20)-diol-(3β.28)；(3S,4aR,6aR,6aR,6bR,8aR,12S,12aR,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,6a,7,8,9,12,12a,13,14,14a-tetradecahydro-1H-picen-3-ol
• CAS: 508-81-6
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: IQXRRXBHWRHUSP-RJFFTXNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  heterobetulin 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以0.42 g的产率得到heterobetulonic acid
  参考文献：
  名称：

  An efficient synthesis of moronic and heterobetulonic acids from allobetulin

  摘要：

  The reaction of acetoxyallobetulin with HClO4 in refluxing Ac2O led to a mixture of diacetoxyheterobetulin (3 beta,28-diacetoxy-18 alpha,19 beta H-urs-20-ene), diacetoxymoradiol (3 beta,28-diacetoxy-olean-18(19)-ene), 3 beta-acetoxy-21 beta-acetyl-20 beta,28-epoxy-18 alpha,19 beta H-ursane, and diacetoxy-delta-erythrodiol (3 beta,28-diacetoxy-olean-13(beta)-ene), which were isolated by column chromatography in yields of 18%, 37%, 39%, and 2%, respectively. Deacetylation of diacetoxyheterobetulin and diacetoxymoradiol followed by Jones oxidation of the corresponding triterpene 3 beta,28-diols led to heterobetulonic and moronic acids with overall yields of 17% and 35% from acetoxyallobetulin, respectively. The reported route makes possible the medium-to-large scale preparation of these pharmacologically important triterpenic acids. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.086
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 苯甲酰氯 作用下， 生成 heterobetulin
  参考文献：
  名称：

  Vystrcil; Klinot, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 3273,3276

  摘要：

  DOI：

文献信息

• SUBSTITUTED TARAXASTANES USEFUL FOR TREATING VIRAL INFECTIONS
  申请人：BRADBURY Barton James

  公开号：US20070197646A1

  公开（公告）日：2007-08-23

  Substituted taraxastanes useful for treating viral infections, are provided herein. Thus, in a first aspect, the invention provides compounds of Formula I and the pharmaceutically acceptable salts thereof, wherein the variables R 1 , R 2 , and X are defined herein. The compounds described herein are thought to act by inhibiting retroviral maturation, including maturation of encapsulated retroviruses viruses, such as the HIV viruses, HIV-1 and HIV-2. Pharmaceutical compositions comprising such compounds of Formula I are included herein. Methods of using such compounds to treat human patients infected with an HIV virus and reducing the mortality of AIDS are also provided herein.

  提供了用于治疗病毒感染的替代性taraxastanes。因此，在第一个方面，本发明提供了公式I的化合物及其药用盐，其中变量R1、R2和X在此定义。这里描述的化合物被认为通过抑制逆转录病毒成熟来发挥作用，包括包膜逆转录病毒病毒的成熟，如HIV病毒、HIV-1和HIV-2。本文还包括包含公式I化合物的药物组合物。提供了使用这种化合物治疗感染HIV病毒的人类患者并减少艾滋病死亡率的方法。
• Zur Kenntnis der Triterpene. 115. Mitteilung. Über das Hetero-lupen
  作者：O. Jeger、Hs. K. Krüsi、L. Ruzicka

  DOI：10.1002/hlca.19470300417

  日期：1947.6.14
• Klinot,J.; Vystrcil,A., Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 516 - 530
  作者：Klinot,J.、Vystrcil,A.

  DOI：——

  日期：——
• Sejbal, Jan; Klinotova, Eva; Bludska, Marketa, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 4, p. 1036 - 1042
  作者：Sejbal, Jan、Klinotova, Eva、Bludska, Marketa、Klinot, Jiri、Budesinsky, Milos

  DOI：——

  日期：——
• Dischendorfer; Grillmayer, Monatshefte fur Chemie, 1926, vol. 47, p. 424
  作者：Dischendorfer、Grillmayer

  DOI：——

  日期：——