(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-3a-(trityloxymethyl)-2,3,4,5,6,7,7a,11b,12,13,13a,13b-dodecahydro-1H-cyclopenta[a]chrysen-9-one | 1131502-22-1

• 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: (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-3a-(trityloxymethyl)-2,3,4,5,6,7,7a,11b,12,13,13a,13b-dodecahydro-1H-cyclopenta[a]chrysen-9-one
• CAS: 1131502-22-1
• 化学式: C₄₉H₆₀O₃
• 分子量: 697.014
• InChiKey: XYAJUXKHGXRPFQ-NFFXIOFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  52
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-3a-(trityloxymethyl)-2,3,4,5,6,7,7a,11b,12,13,13a,13b-dodecahydro-1H-cyclopenta[a]chrysen-9-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以798 mg的产率得到28-O-trityl-2β,3β-dihydroxylup-20(29)-en-28-ol
  参考文献：
  名称：

  Efficient Access to 2-Isobetulinic Acid, 2-Isooleanolic Acid, and 2-Isoursolic Acid

  摘要：

  An efficient access to 2-isobetulin, 2-isobetulinic acid 2-isooleanolic acid, and 2-isoursolic acid has been developed The key step is a novel one-pot conversion of 2,3-dihydroxy triterpenes to 3-deoxy-2-oxo triterpenes. This method provides a new access to 3-deoxy-2-substituted pentacyclic triterpenes as potential therapeutic agents against metabolic diseases, tumors, and HIV infection.

  DOI：

  10.1021/jo801232s
• 作为产物：
  描述：

  28-O-trityllup-20(29)-en-28-ol-3-one 在 air 、 potassium tert-butylate 、 盐酸 、 水 作用下， 以 叔丁醇 为溶剂， 反应 10.0h， 生成 (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-3a-(trityloxymethyl)-2,3,4,5,6,7,7a,11b,12,13,13a,13b-dodecahydro-1H-cyclopenta[a]chrysen-9-one
  参考文献：
  名称：

  Efficient Access to 2-Isobetulinic Acid, 2-Isooleanolic Acid, and 2-Isoursolic Acid

  摘要：

  An efficient access to 2-isobetulin, 2-isobetulinic acid 2-isooleanolic acid, and 2-isoursolic acid has been developed The key step is a novel one-pot conversion of 2,3-dihydroxy triterpenes to 3-deoxy-2-oxo triterpenes. This method provides a new access to 3-deoxy-2-substituted pentacyclic triterpenes as potential therapeutic agents against metabolic diseases, tumors, and HIV infection.

  DOI：

  10.1021/jo801232s

文献信息

• Efficient access to isomeric 2,3-dihydroxy lupanes: first synthesis of alphitolic acid
  作者：Jia Hao、Xueli Zhang、Pu Zhang、Jun Liu、Luyong Zhang、Hongbin Sun

  DOI：10.1016/j.tet.2009.07.047

  日期：2009.9

  Alphitolic acid (3) is a naturally occurring lupane type of pentacyclic triterpene, which possesses various pharmacological properties. Efficient synthesis of 3 has been accomplished in 10 steps with an overall yield of 19% starting from the readily available diketone 11. An alternative approach to the key intermediate 17 has also been developed, and based on this approach, 3 could be obtained in 10

  环烷酸（3）是天然存在的戊烷型五环三萜，具有多种药理特性。3的有效合成已从10步中完成，从容易获得的二酮11开始，总产率为19％。还开发了关键中间体17的替代方法，基于该方法，可以从10开始以10步获得3，总产率为26％（从11开始）。此外，七其他异构-2,3-二羟基lupanes 4 - 10已被合成。合成的三萜3 – 10 评估了它们对兔肌肉GPa（RMGPa）的抑制活性，其中一些对RMGPa表现出中等的抑制活性。
• Efficient synthesis and biological evaluation of epiceanothic acid and related compounds
  作者：Pu Zhang、Li Xu、Keduo Qian、Jun Liu、Luyong Zhang、Kuo-Hsiung Lee、Hongbin Sun

  DOI：10.1016/j.bmcl.2010.11.004

  日期：2011.1

  Epiceanothic acid () is a naturally occurring, but very rare pentacyclic triterpene with a unique pentacyclic triterpene (PT) structure. An efficient synthesis of starting from betulin () has been accomplished in 12-steps with a total yield of 10% in our study. Compound and selected synthetic intermediates were further evaluated as anti-HIV-1 agents, inhibitors of glycogen phosphorylase (GP), and cytotoxic

  Epiceanothic Acid () 是一种天然存在但非常罕见的五环三萜，具有独特的五环三萜 (PT) 结构。在我们的研究中，以桦木醇()为起始原料，经过12步的高效合成，总收率为10%。化合物和选定的合成中间体作为抗 HIV-1 药物、糖原磷酸化酶 (GP) 抑制剂和细胞毒性药物进行了进一步评估。化合物表现出中等程度的 HIV-1 抑制作用。最重要的是，具有开放 A 环的化合物表现出显着的 GP 抑制活性，IC 值为 0.21μM，表明其具有作为抗糖尿病药物开发的潜力。另一方面，具有闭合A环的化合物对A549和MCF-7人类肿瘤细胞系表现出有效的细胞毒性，IC值分别为0.89和0.33μM。这些结果表明 PT 的 A 环是一个重要的药效团，可以对其进行修饰以涉及不同的生物活性。