白桦脂醇-3-乙酸酯 | 27570-20-3

• 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
• 中文名称: 白桦脂醇-3-乙酸酯
• 英文名称: betulin monoacetate
• 英文别名: 3-O-acetylbetulin；3β-acetoxylup-20 (29)-ene-3,28-diol；[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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: 27570-20-3
• 化学式: C₃₂H₅₂O₃
• 分子量: 484.763
• InChiKey: XUDTWJGGQFHXCR-VFUWXHBOSA-N

物化性质

• 溶解度：
  二甲基甲酰胺：5mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  白桦脂醇-3-乙酸酯 在 氢氧化钾 、 tBuOCrO3H 作用下， 以 甲醇 为溶剂， 生成 白桦脂酸
  参考文献：
  名称：

  Synthesis of Glycosides of Lupane-Type Triterpene Acids

  摘要：

  A preparative synthesis of glucosides of the lupane-type triterpene acids betulinic, dihydrobetulinic, betulonic, dihydrobetulonic. and 3,20-dioxo-30-norlupan-28-oic was proposed. Glycosylation of 3-hydroxyacids by alpha-acetohronioglucose (ABG) with Ag2O was performed in pyridine (Py) to form glycosides at C-28, repeated glycosylation of which by these same reagents but in CH2Cl2 generated a glycoside bond at C-3 to form bisglucosides 28- Glucosides of ketoacids were formed in high yields in both Py and CH2Cl2.

  DOI：

  10.1023/b:conc.0000018113.79735.34
• 作为产物：
  描述：

  白桦脂醇 在 titanium(IV) isopropylate 、 4-二甲氨基吡啶 作用下， 以 吡啶 、 丙醇 为溶剂， 反应 11.0h， 生成 白桦脂醇-3-乙酸酯
  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

• Mitochondria‐Targeted Triphenylphosphonium Conjugated C‐3 Modified Betulin: Synthesis, Antitumor Properties and Mechanism of Action
  作者：Geng Xu、Xiaojia Xu、Jiansong Liu、Qi Jia、Changhong Ke、Hanyuan Zhang、Chao Xu、E Ou、Wen Tan、Yu Zhao

  DOI：10.1002/cmdc.202100659

  日期：2022.2.16

  Mitochondria-targeted triphenylphosphonium conjugated C-3 modified betulin were synthesized and evaluated against tumor and normal cells. The screening results enable the SAR analysis and identified a new conjugate 13 i with significant cytotoxicity against HCT116 and good selectivity for normal cell NCM460. Conjugate 13 i caused ROS accumulation, decreased ψM, and induced apoptosis through mitochondrial

  合成了靶向线粒体的三苯基鏻缀合的 C-3 修饰的白桦脂素，并针对肿瘤和正常细胞进行了评估。筛选结果使 SAR 分析成为可能，并确定了一种新的缀合物13 i，它对 HCT116 具有显着的细胞毒性，对正常细胞 NCM460 具有良好的选择性。Conjugate 13 i引起 ROS 积累，降低 ψM，并通过线粒体途径诱导细胞凋亡。
• 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。
• 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
• Organic photochemistry - part II, photochemical synthesis of the naturally occurring triterpene lactone, 3 β-hydroxy lupan-28, 13 β-olide
  作者：Swapan K. Nag、Samarendra N. Bose

  DOI：10.1016/s0040-4039(00)99143-3

  日期：1989.1

  The photochemical synthesis of the title lactone was achieved by irradiation in the presence of Pb(IV) acetate alone or Pb(IV) acetate + calcium carbonate + iodine or mercuric oxide + iodine. Chiroptical measurements (CD) of this and other related lactones provided convincing evidence in support of the lactone ring structure.

  标题内酯的光化学合成是通过在单独的乙酸铅（IV）或乙酸铅（IV）+碳酸钙+碘或氧化汞+碘的存在下进行辐照而实现的。对该内酯和其他相关内酯的整脊测量（CD）提供了令人信服的证据来支持内酯环结构。