methyl 3β-O-carboxypropionylurs-12-ene-28-oate

• 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: methyl 3β-O-carboxypropionylurs-12-ene-28-oate
• 英文别名: 4-[[(3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-8a-methoxycarbonyl-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-yl]oxy]-4-oxobutanoic acid
• 化学式: C₃₅H₅₄O₆
• 分子量: 570.81
• InChiKey: STQFTLGZKHJNKE-MQCXLNOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3β-O-carboxypropionylurs-12-ene-28-oate 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 methyl 3β-O-[4-(6-aminohexylamino)-4-oxo-butyryl]urs-12-ene-28-oate
  参考文献：
  名称：

  The Novel Synthetic Triterpene Methyl 3β-<i>O</i>-[4-(2-Aminoethylamino)-4-oxo-butyryl]olean-12-ene-28-oate Inhibits Breast Tumor Cell Growth <i>in</i> <i>Vitro</i> and <i>in</i> <i>Vivo</i>

  摘要：

  Oleanolic and ursolic acids were used as lead compounds to synthesize a series of pentacyclic triterpenoid derivatives bearing ethylenediamine, butanediamine, or hexanediamine groups at the C-3 position. The potential antiproliferative activity of these compounds was examined in A549 (human non-small cell lung cancer cells), MCF-7 (human breast cancer cells), and HeLa (human cervical carcinoma cells) cells. Methyl 3 ss-O-[4-(2-aminoethylamino)-4-oxo-butyryl]olean-12-ene-28-oate (DABO-Me) was identified as a promising antiproliferative agent in vitro and in vivo. DABO-Me strongly suppressed the proliferation of A549, MCF-7, and HeLa cells (IC50 = 4-7 mu M). In MCF-7 cells, DABO-Me upregulated the pro-apoptotic protein Bax, downregulated the anti-apoptotic protein Bcl-2, promoted the release of cytochrome c, and activated caspase-3/9. Transwell and flow cytometry assays showed that DABO-Me inhibited MCF-7 cell proliferation, migration, and invasion, and induced apoptosis and S phase arrest. In vitro and in vivo experiments indicated that DABO-Me inhibited MCF-7 cell proliferation and suppressed tumor growth. Taken together, these results indicate that DABO-Me could be developed as an effective antitumor drug.

  DOI：

  10.1248/cpb.c20-00353
• 作为产物：
  描述：

  熊果酸 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 methyl 3β-O-carboxypropionylurs-12-ene-28-oate
  参考文献：
  名称：

  设计，合成和生物功能评价新型五环三萜带有O- [4-（1-哌嗪基）-4-氧代-丁酰基部分作为抗增殖剂。

  摘要：

  合成了一系列带有O- [4-（1-哌嗪基）-4-氧代-丁酰基部分的五环三萜衍生物，并研究了它们潜在的抗增殖活性。五环三萜类化合物的衍生物是通过四步或六步合成程序合成的。使用Cell Counting Kit-8方法评估活性研究，并对A549细胞，MCF-7细胞和Hela细胞进行Western印迹分析。化合物3-O- [4-（1-哌嗪基）-4-氧代-丁酰基] olean-12-ene-28-oate（OA-4）和化合物2-O- [4-（1-哌嗪基）-发现4-氧代-丁酰基] -3，23-二羟基urs-12-烯-28-油酸酯（AA-5）是有前途的抗增殖剂。这些化合物显示出进一步优化作为抗肿瘤药物的潜力。

  DOI：

  10.1016/j.bmcl.2015.08.076

文献信息

• Design, synthesis, and biofunctional evaluation of novel pentacyclic triterpenes bearing O-[4-(1-piperazinyl)-4-oxo-butyryl moiety as antiproliferative agents
  作者：Chun-hui Zhao、Cui-li Zhang、Jin-jie Shi、Xi-yan Hou、Bin Feng、Long-xuan Zhao

  DOI：10.1016/j.bmcl.2015.08.076

  日期：2015.10

  A series of pentacyclic triterpenoids derivatives bearing O-[4-(1-piperazinyl)-4-oxo-butyryl moiety has been synthesized and investigated for their potential antiproliferative activities. Pentacyclic triterpenoids derivative compounds were synthesized by a four or six step synthetic procedure. The activity studies were evaluated using Cell Counting Kit-8 method, and Western blotting analysis on A549

  合成了一系列带有O- [4-（1-哌嗪基）-4-氧代-丁酰基部分的五环三萜衍生物，并研究了它们潜在的抗增殖活性。五环三萜类化合物的衍生物是通过四步或六步合成程序合成的。使用Cell Counting Kit-8方法评估活性研究，并对A549细胞，MCF-7细胞和Hela细胞进行Western印迹分析。化合物3-O- [4-（1-哌嗪基）-4-氧代-丁酰基] olean-12-ene-28-oate（OA-4）和化合物2-O- [4-（1-哌嗪基）-发现4-氧代-丁酰基] -3，23-二羟基urs-12-烯-28-油酸酯（AA-5）是有前途的抗增殖剂。这些化合物显示出进一步优化作为抗肿瘤药物的潜力。
• 基于顺铂衍生的含熊果酸配体的四价铂抗癌配合物及其制备方法和应用
  申请人：南京菲力康医药科技有限公司

  公开号：CN113651868B

  公开（公告）日：2022-05-10

  本发明属于药物化学领域，具体涉及一种基于顺铂衍生的含熊果酸配体的四价铂抗癌配合物及其制备方法和应用。本发明公开的该系列含熊果酸配体的Pt(IV)配合物以顺铂为基础母核，在轴向一端引入熊果酸衍生配体，另一端引入‑Cl或‑OH基团；或在轴向两端均引入熊果酸衍生配体，该系列Pt(IV)配合物的制备所使用的原料价廉易得，方法简单易行，易于操作，适用于规模化生产。体外实验表明Pt(IV)配合物US‑CIS‑CL和US‑CIS‑OH显示出很高的抗癌活性，优于顺铂，并具有较好的癌细胞选择性，同时对顺铂耐药的癌细胞也表现出良好的抗癌活性，有潜力开发成为一种高效低毒并克服顺铂耐药的抗癌新药。
• The Novel Synthetic Triterpene Methyl 3β-&lt;i&gt;O&lt;/i&gt;-[4-(2-Aminoethylamino)-4-oxo-butyryl]olean-12-ene-28-oate Inhibits Breast Tumor Cell Growth &lt;i&gt;in&lt;/i&gt; &lt;i&gt;Vitro&lt;/i&gt; and &lt;i&gt;in&lt;/i&gt; &lt;i&gt;Vivo&lt;/i&gt;
  作者：Bin Feng、Chunhui Zhao、Jiaqi Li、Jiawen Yu、Yang Zhang、Xiyue Zhang、Tian Tian、Longxuan Zhao

  DOI：10.1248/cpb.c20-00353

  日期：2020.10.1

  Oleanolic and ursolic acids were used as lead compounds to synthesize a series of pentacyclic triterpenoid derivatives bearing ethylenediamine, butanediamine, or hexanediamine groups at the C-3 position. The potential antiproliferative activity of these compounds was examined in A549 (human non-small cell lung cancer cells), MCF-7 (human breast cancer cells), and HeLa (human cervical carcinoma cells) cells. Methyl 3 ss-O-[4-(2-aminoethylamino)-4-oxo-butyryl]olean-12-ene-28-oate (DABO-Me) was identified as a promising antiproliferative agent in vitro and in vivo. DABO-Me strongly suppressed the proliferation of A549, MCF-7, and HeLa cells (IC50 = 4-7 mu M). In MCF-7 cells, DABO-Me upregulated the pro-apoptotic protein Bax, downregulated the anti-apoptotic protein Bcl-2, promoted the release of cytochrome c, and activated caspase-3/9. Transwell and flow cytometry assays showed that DABO-Me inhibited MCF-7 cell proliferation, migration, and invasion, and induced apoptosis and S phase arrest. In vitro and in vivo experiments indicated that DABO-Me inhibited MCF-7 cell proliferation and suppressed tumor growth. Taken together, these results indicate that DABO-Me could be developed as an effective antitumor drug.