3-O-acetylbetulinal | 27570-21-4

• 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-acetylbetulinal
• 英文别名: 3-O-acetylbetulinic aldehyde；3-acetylbetulinic aldehyde；3-Acetylbetulinaldehyde；[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-formyl-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]chrysen-9-yl] acetate
• CAS: 27570-21-4
• 化学式: C₃₂H₅₀O₃
• 分子量: 482.747
• InChiKey: VATQYYFSJMNJAL-VFUWXHBOSA-N

物化性质

• 熔点：
  199-200 °C(Solv: ethyl ether (60-29-7); methanol (67-56-1))
• 沸点：
  527.0±33.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿：10 mg/ml，DMF：1 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-O-acetylbetulinal 在 一水合肼 、 potassium hydroxide 作用下， 以 二乙二醇 为溶剂， 反应 6.0h， 以65%的产率得到羽扇豆醇
  参考文献：
  名称：

  从桦木脑合成羽扇豆醇

  摘要：

  Lupeol (1) 是一种五环羽扇豆型三萜，具有重要的药理特性，例如抗血管生成、抗菌、抗增殖、抗炎和降低胆固醇。它已在治疗炎症、关节炎、糖尿病以及心脏病和肿瘤疾病的体外和体内研究中显示出很高的药理学潜力 [1, 2]。因此，这项工作的目标是开发一种改良的羽扇豆醇合成方案。

  DOI：

  10.1007/s10600-019-02805-5
• 作为产物：
  描述：

  白桦脂醇 在 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 pyridinium chlorochromate 作用下， 以 吡啶 、 丙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 3-O-acetylbetulinal
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Betulin Derivatives with Aromatic Hydrazone Side Chain as Potential Anticancer Agents

  摘要：

  一系列新型的白桦酸-28-腙衍生物（7a-7o）被合成。所有化合物都在四种人类癌细胞（HepG2，MCF-7，HCT-116和A549）中进行了体外细胞毒性评估。其中，化合物7l在MCF-7细胞中表现出最强的细胞毒性，其IC50值（抑制50％细胞生长的测试化合物的浓度）为7.37±0.38μM。初步的细胞机制研究表明，化合物7l可以诱导MCF-7细胞凋亡。以上发现表明，化合物7l可能被用作抗肿瘤药物的先导化合物，具有改善疗效的作用。

  DOI：

  10.21577/0103-5053.20210140

文献信息

• Synthesis, Encapsulation and Antitumor Activity of New Betulin Derivatives
  作者：René Csuk、Alexander Barthel、Ronny Sczepek、Bianka Siewert、Stefan Schwarz

  DOI：10.1002/ardp.201000232

  日期：2011.1

  Novel betulin derivatives were prepared and tested for their antitumor activity. Starting from 3‐O‐acetyl‐ or 3‐O‐methyl‐betulinic aldehyde, the synthesis of C‐28 ethynyl derivatives was performed; their subsequent transformation with several 1,3‐dipolarophiles afforded pyrazoles and 1,2,3‐triazoles. Their screening for antitumor activity was performed in a panel of 15 human cancer cell lines by a

  制备了新的桦木脑衍生物并测试了它们的抗肿瘤活性。以3-O-乙酰基-或3-O-甲基-桦木醛为原料，合成C-28乙炔基衍生物；他们随后与几个 1,3- 偶极亲和试剂进行转化，得到吡唑和 1,2,3-三唑。他们的抗肿瘤活性筛选是通过比色 SRB 测定在一组 15 个人类癌细胞系中进行的。因此，几种化合物显示出比桦木酸更高的细胞毒性。此外，研究了将引线结构 7 封装到脂质体中。染料排斥试验和 DNA 阶梯实验的结果为细胞凋亡提供了证据。
• Synthesis and biological evaluation of antitumor-active γ-butyrolactone substituted betulin derivatives
  作者：René Csuk、Alexander Barthel、Stefan Schwarz、Harish Kommera、Reinhard Paschke

  DOI：10.1016/j.bmc.2010.02.042

  日期：2010.4

  The plant triterpenes betulin and betulinic acid (BA) are triterpenes featuring interesting pharmacological properties. Starting from substituted betulinic aldehydes, we used them as lead structures for the synthesis of several γ-butyrolactones and butenolides. Their antitumor activity was examined for 15 cancer cell lines using a SRB-assay and their apoptotic action was documented by trypan-blue test

  植物三萜类桦木和桦木酸（BA）是具有有趣药理特性的三萜类。从取代的桦木醛开始，我们将它们用作合成几种γ-丁内酯和丁烯化物的前导结构。使用SRB测定法检测了它们对15种癌细胞系的抗肿瘤活性，并通过台盼蓝试验和DNA阶梯检测证明了它们的凋亡作用。几种化合物显示出比桦木酸更高的活性。
• [EN] TRITERPENE AMINE DERIVATIVES<br/>[FR] DÉRIVÉS D'AMINE TRITERPÉNIQUE
  申请人：DFH THERAPEUTICS

  公开号：WO2020006510A1

  公开（公告）日：2020-01-02

  The present invention concerns novel pharmaceutically active triterpene amine derivatives, pharmaceutical compositions containing the same, their use as medicaments, and the use of the compounds for the manufacture of specific medicaments. The present invention also concerns a method of treatment involving administration of the triterpene amine compounds. Specifically, the compounds are derivatives of betulinic acid having substitutions at one or more of the C-3, C-28 and C-19 positions as further described herein. The novel compounds are useful as antiretroviral agents. In particular, the novel compounds are useful for the treatment of Human Immunodeficiency Virus-1 (HIV-1).

  本发明涉及新型具有药用活性的三萜胺衍生物，含有这些衍生物的药物组合物，它们作为药物的用途，以及用这些化合物制造特定药物的用途。本发明还涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉及涉
• 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。
• TRITERPENES DERIVATIVES AND USES THEREOF AS ANTITUMOR AGENTS OR ANTI-INFLAMMATORY AGENTS
  申请人：PICHETTE ANDRE

  公开号：US20080167254A1

  公开（公告）日：2008-07-10

  A compound of formula (1): wherein R 1 is selected from the group consisting of H, α-L-Rhamnopyranose, α-D-Mannopyranose, β-D-Xylopyranose, β-D-Glucopyranose, and α-D-Arabinopyranose; R 2 is selected from CH 3 , COOH, CH 2 OH, COOCH 3 and CH 2 O-α-D-Arabinopyranose; with the proviso that the compound of formula (I) is not a compound of formula (I) wherein R 1 is β-D-Glucopyranose and R 2 is COOH; wherein R 1 is α-L-Rhamnopyranose and R 2 is CH 3 ; wherein R 1 is β-D-Glucopyranose and R 2 is CH 2 OH; wherein R 1 is β-D-Xylopyranose and R 2 is CH 2 OH; wherein R 1 is α-L-Rhamnopyranose and R 2 is COOCH 3 , wherein R 1 is H and R 2 is CH 3 ; wherein R 1 is H and R 2 is CH 2 OH; wherein R 1 is H and R 2 is COOH; or wherein R 1 is H and R 2 is COOCH 3 , or a pharmaceutically acceptable salt thereof.

  式（1）的化合物：其中R1选自H、α-L-葡萄糖苷、α-D-甘露糖苷、β-D-木糖苷、β-D-葡萄糖苷和α-D-阿拉伯糖苷组成的群；R2选自CH3、COOH、CH2OH、COOCH3和CH2O-α-D-阿拉伯糖苷；但化合物的式（I）不是式（I）中R1为β-D-葡萄糖苷且R2为COOH的化合物；其中R1为α-L-葡萄糖苷且R2为CH3；其中R1为β-D-葡萄糖苷且R2为CH2OH；其中R1为β-D-木糖苷且R2为CH2OH；其中R1为α-L-葡萄糖苷且R2为COOCH3；其中R1为H且R2为CH3；其中R1为H且R2为CH2OH；其中R1为H且R2为COOH；或其中R1为H且R2为COOCH3，或其药学上可接受的盐。