3-O-acetyl-28-O-tetrahydropyranylbetulin | 189571-53-7

• 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: 3-O-acetyl-28-O-tetrahydropyranylbetulin
• 英文别名: betulin 3-acetoxy-28-tetrahydropyrane ether；(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-((tetrahydro-2H-pyran-2-yloxy)methyl)icosahydro-1H-cyclopenta[a]chrysen-9-ylacetate；[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(oxan-2-yloxymethyl)-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate
• CAS: 189571-53-7
• 化学式: C₃₇H₆₀O₄
• 分子量: 568.881
• InChiKey: HPTAJJZKJDDMAN-JHYCHLOKSA-N

物化性质

• 熔点：
  249-250 °C
• 沸点：
  596.2±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-28-O-tetrahydropyranylbetulin 在 chromium(VI) oxide 、 硫酸 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 61.5h， 生成 白桦脂酸
  参考文献：
  名称：

  A Concise Semi-Synthetic Approach to Betulinic Acid from Betulin

  摘要：

  Betulin was convert to betulinic acid using two different synthetic routes. The first approach involved an oxidation of betulin using Jones' reagent to betulonic acid and subsequent NaBH4 reduction to betulinic acid. The second approach involved steps utilizing different protecting groups on the alcohol functional groups of betulin and Jones' oxidation to circumvent the isomerization of the secondary alcohol of betulinic acid.

  DOI：

  10.1080/00397919708006099
• 作为产物：
  描述：

  白桦脂醇 在 吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 108.0h， 生成 3-O-acetyl-28-O-tetrahydropyranylbetulin
  参考文献：
  名称：

  A Concise Semi-Synthetic Approach to Betulinic Acid from Betulin

  摘要：

  Betulin was convert to betulinic acid using two different synthetic routes. The first approach involved an oxidation of betulin using Jones' reagent to betulonic acid and subsequent NaBH4 reduction to betulinic acid. The second approach involved steps utilizing different protecting groups on the alcohol functional groups of betulin and Jones' oxidation to circumvent the isomerization of the secondary alcohol of betulinic acid.

  DOI：

  10.1080/00397919708006099

文献信息

• Betulin-Derived Compounds as Inhibitors of Alphavirus Replication
  作者：Leena Pohjala、Sami Alakurtti、Tero Ahola、Jari Yli-Kauhaluoma、Päivi Tammela

  DOI：10.1021/np9003245

  日期：2009.11.30

  shown to inhibit Sindbis virus, with IC50 values of 0.5, 1.9, and 6.1 μM, respectively. The latter three compounds also had significant synergistic effects against SFV when combined with 3′-amino-3′-deoxyadenosine. In contrast to previous work on other viruses, the antiviral activity of 13 was mapped to take place in virus replication phase. The efficacy was also shown to be independent of external

  本文描述了自然存在的三萜类桦木精蛋白的合成衍生物对Semliki森林病毒（SFV）复制的抑制作用（1）。对C-3和C-28上的OH基团以及C-20-C-29双键进行了化学修饰。还测定了一组杂环白桦蛋白衍生物。C-3的游离或乙酰化OH基团被确定为抗SFV活性的重要结构贡献者，3,28-di- O-乙酰基白蛋白（4）是最有效的衍生物（IC 50值为9.1μM ）。桦木酸（13），28- O-四氢吡喃基贝特林（17）和三唑烷衍生物（41）还显示可抑制Sindbis病毒，IC 50值分别为0.5、1.9和6.1μM。当与3'-氨基-3'-脱氧腺苷联合使用时，后三种化合物还对SFV具有显着的协同作用。与以前对其他病毒的研究相比，13的抗病毒活性被映射为在病毒复制阶段发生。还显示功效独立于外部鸟苷补充。
• Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin
  申请人：Xu Ze-Qi

  公开号：US20070232577A1

  公开（公告）日：2007-10-04

  The present invention comprises small molecule inhibitors of cell proliferative conditions, in particular cancer and conditions associated with cancer. For example, associated malignancies include ovarian cancer, cervical cancer, breast cancer, colorectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases. Thus, the present invention also comprising pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.

  本发明包括细胞增殖状况的小分子抑制剂，特别是癌症及与癌症相关的状况。例如，相关的恶性肿瘤包括卵巢癌、宫颈癌、乳腺癌、结直肠癌和胶质母细胞瘤等。因此，本发明的化合物对于治疗、预防和/或抑制这些疾病是有用的。因此，本发明还包括包含这些化合物的药物配方以及使用这些化合物和配方来抑制癌症并治疗、预防或抑制上述疾病的方法。
• WO2007/141389
  申请人：——

  公开号：——

  公开（公告）日：——
• A Concise Semi-Synthetic Approach to Betulinic Acid from Betulin
  作者：Darrick S. H. L. Kim、Zhidong Chen、van Tuyen Nguyen、John M. Pezzuto、Shengxiang Qiu、Zhi-Zhen Lu

  DOI：10.1080/00397919708006099

  日期：1997.5

  Betulin was convert to betulinic acid using two different synthetic routes. The first approach involved an oxidation of betulin using Jones' reagent to betulonic acid and subsequent NaBH4 reduction to betulinic acid. The second approach involved steps utilizing different protecting groups on the alcohol functional groups of betulin and Jones' oxidation to circumvent the isomerization of the secondary alcohol of betulinic acid.