3-bromopropyl betulonate | 1187656-58-1

• 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: 3-bromopropyl betulonate
• 英文别名: 3-bromopropyl (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate
• CAS: 1187656-58-1
• 化学式: C₃₃H₅₁BrO₃
• 分子量: 575.67
• InChiKey: QJUMBADDLCQOEG-KZDAZGORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  37
• 可旋转键数：
  6
• 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-bromopropyl betulonate 在 silver nitrate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.0h， 以85%的产率得到betulonic acid (3-nitrooxypropyl) ester
  参考文献：
  名称：

  Design, synthesis, and anti-tumor activity of novel betulinic acid derivatives

  摘要：

  Seventeen new derivatives of betulinic acid (BA) with potential anti-tumor activity have been synthesized. In order to improve the bioactivity of BA, we connected BA and nitric oxide donors together via different linkers. The results of the biological activity of these derivatives showed that four compounds exhibited obvious cytotoxicity against human hepatocellular carcinoma cells in vitro.

  DOI：

  10.1080/10286020.2013.870998
• 作为产物：
  描述：

  白桦脂酸 在 Jones reagent 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 6.25h， 生成 3-bromopropyl betulonate
  参考文献：
  名称：

  Design, synthesis, and anti-tumor activity of novel betulinic acid derivatives

  摘要：

  Seventeen new derivatives of betulinic acid (BA) with potential anti-tumor activity have been synthesized. In order to improve the bioactivity of BA, we connected BA and nitric oxide donors together via different linkers. The results of the biological activity of these derivatives showed that four compounds exhibited obvious cytotoxicity against human hepatocellular carcinoma cells in vitro.

  DOI：

  10.1080/10286020.2013.870998

文献信息

• Synthesis and biological evaluation of betulonic acid derivatives as antitumor agents
  作者：Sheng-Jie Yang、Ming-Chuan Liu、Qi Zhao、De-Yu Hu、Wei Xue、Song Yang

  DOI：10.1016/j.ejmech.2015.04.006

  日期：2015.5

  Structural modification was performed at the C-28 position of betulonic acid (BetA). Twenty-five BetA derivatives were synthesized, and evaluated for their antitumor activities against MGC-803, PC3, Bcap-37, A375, and MCF-7 human cancer cell lines by MTT assay. Among the derivatives, most of the derivatives had significant antiproliferative ability (IC50 < 19 μM). Compound 3k, the most active compound

  在丁二酸（BetA）的C-28位置进行结构修饰。合成了二十五个BetA衍生物，并通过MTT分析评估了它们对MGC-803，PC3，Bcap-37，A375和MCF-7人癌细胞系的抗肿瘤活性。在衍生物中，大多数衍生物具有显着的抗增殖能力（IC 50  <19μM）。活性最高的化合物3k在五种癌细胞系上的IC 50值分别为3.6、5.6、4.2、7.8和5.2μM，并被选择用于随后的荧光染色和流式细胞术分析细胞凋亡。结果表明，复合3k可以诱导MGC-803细胞凋亡，在10μM处理36 h后，凋亡率达到28.33％。另外，对癌细胞凋亡信号通路的研究表明，化合物3k诱导的MGC-803细胞的凋亡可能是通过线粒体内在途径进行的。
• Synthesis of Conjugates of Lupane-Type Pentacyclic Triterpenoids with 2-Aminoethane- and N-Methyl-2-Aminoethanesulfonic Acids. Assessment of in vitro Toxicity
  作者：N. G. Komissarova、S. N. Dubovitskii、O. V. Shitikova、E. M. Vyrypaev、L. V. Spirikhin、E. M. Eropkina、T. G. Lobova、M. Yu. Eropkin、M. S. Yunusov

  DOI：10.1007/s10600-017-2153-6

  日期：2017.9

  Conjugates of betulin and betulinic and betulonic acids with 2-aminoethane- and N-methyl-2-aminoethanesulfonic acids were synthesized for the first time and were interesting as potential biologically active compounds. Experiments in vitro in MDCK cell culture using the MTT assay found that betulin and betulinic-acid derivatives with aminoethanesulfonic acid bound to triterpene C-3 or C-28 through an ester linker were less toxic than the native compounds.

  首次合成了与2-氨基乙烷酸及N-甲基-2-氨基乙烷磺酸结合的白桦脂醇和白桦脂酸衍生物，这些化合物因其潜在的生物活性而备受关注。在MDCK细胞培养中进行MTT试验的体外实验表明，通过酯连接体将氨基乙烷磺酸结合在三萜C-3或C-28位置的白桦脂醇和白桦脂酸衍生物，其毒性低于母体化合物。
• Novel NO-releasing derivatives of betulinic acid with antitumor activity
  作者：Jin-Hong Liu、Zi-Fei Zhu、Jia Tang、Ai-Qin Jiang、Liu-Fang Hu、Li Chen

  DOI：10.1016/j.cclet.2015.04.002

  日期：2015.6

  Thirteen novel NO-releasing derivatives of betulinic acid (BA) bearing two types of NO-donors (nitrates and furoxans) were synthesized and evaluated for their antitumor activity. The results showed that furoxan-based derivatives exhibited higher antitumor activity than nitrate-based derivatives, with compounds 11a and 11b displaying promising potency against B16 cell lines and HepG2 cell lines (IC50 < 1 mu mol/L). We supposed that NO-releasing amount of these derivatives which can be detected by Griess method may contribute more to their antitumor activity. As a result, furoxan-based derivatives released larger amount of NO than that of nitrate-based derivatives, which partially explained the higher anti-tumor activity of the former. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• Design, synthesis, and anti-tumor activity of novel betulinic acid derivatives
  作者：Jin-Hong Liu、Jia Tang、Zi-Fei Zhu、Li Chen

  DOI：10.1080/10286020.2013.870998

  日期：2014.1.2

  Seventeen new derivatives of betulinic acid (BA) with potential anti-tumor activity have been synthesized. In order to improve the bioactivity of BA, we connected BA and nitric oxide donors together via different linkers. The results of the biological activity of these derivatives showed that four compounds exhibited obvious cytotoxicity against human hepatocellular carcinoma cells in vitro.