28-[(tetrahydro-2H-pyran-2-yl)oxy]lup-20(29)-en-3-one | 689277-21-2

• 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: 28-[(tetrahydro-2H-pyran-2-yl)oxy]lup-20(29)-en-3-one
• 英文别名: (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-((tetrahydro-2H-pyran-2-yloxy)methyl)octadecahydro-1H-cyclopenta[a]chrysen-9(5bH)-one；(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(oxan-2-yloxymethyl)-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
• CAS: 689277-21-2
• 化学式: C₃₅H₅₆O₃
• 分子量: 524.828
• InChiKey: ZCUSORUZMOCNHS-ARQWUAQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  28-[(tetrahydro-2H-pyran-2-yl)oxy]lup-20(29)-en-3-one 在 盐酸羟胺 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 23.0h， 生成 28-hydroxylupa-2,20(29)-dieno[2,3-d]isoxazole
  参考文献：
  名称：

  杂环融合的卢烷三萜类化合物可抑制利什曼原虫donovani amastigotes †

  摘要：

  报道了杂环桦木素衍生物的合成及其对利什曼原虫的活性。丁二酸用作通用中间体。在异戊烷骨架的2,3-位引入了几个不同的稠合杂环，包括异恶唑，吡嗪，吡啶，吲哚和吡唑环。同样，对28位进行了修改。三种化合物，5，8和25，显示出低的微摩尔活性，IC 50个分别为13.2，4.3和7.2μM，值。化合物8表现出最佳的活性和选择性，并使用5μM的浓度在受感染的巨噬细胞上测试了其活性，没有显示出巨噬细胞毒性。有趣的是，化合物8对轴突性变形虫和利什曼原虫感染的巨噬细胞的活性是相似的。

  DOI：

  10.1039/c3md00282a
• 作为产物：
  描述：

  白桦脂醇 在 4-甲基苯磺酸吡啶 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 28-[(tetrahydro-2H-pyran-2-yl)oxy]lup-20(29)-en-3-one
  参考文献：
  名称：

  杂环融合的卢烷三萜类化合物可抑制利什曼原虫donovani amastigotes †

  摘要：

  报道了杂环桦木素衍生物的合成及其对利什曼原虫的活性。丁二酸用作通用中间体。在异戊烷骨架的2,3-位引入了几个不同的稠合杂环，包括异恶唑，吡嗪，吡啶，吲哚和吡唑环。同样，对28位进行了修改。三种化合物，5，8和25，显示出低的微摩尔活性，IC 50个分别为13.2，4.3和7.2μM，值。化合物8表现出最佳的活性和选择性，并使用5μM的浓度在受感染的巨噬细胞上测试了其活性，没有显示出巨噬细胞毒性。有趣的是，化合物8对轴突性变形虫和利什曼原虫感染的巨噬细胞的活性是相似的。

  DOI：

  10.1039/c3md00282a

文献信息

• 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。
• 23-Substituted Derivatives of Lupane-type Pentacyclic Triterpenoids
  申请人：Koohang Ali

  公开号：US20100144688A1

  公开（公告）日：2010-06-10

  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 comprises pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.

  本发明包括针对细胞增殖病症的小分子抑制剂，特别是癌症及与癌症相关的病症。例如，相关的恶性肿瘤包括卵巢癌、宫颈癌、乳腺癌、结肠直肠癌和胶质母细胞瘤等。因此，本发明的化合物可用于治疗、预防和/或抑制这些疾病。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。
• Lupane-Type Triterpenoids Modified at 30-Position and Analogues Thereof
  申请人：Koohang Ali

  公开号：US20090062243A1

  公开（公告）日：2009-03-05

  The present invention comprises lupine-type triterpenoids that inhibit cell proliferations, 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.

  本发明涉及一种羽扇豆型三萜类物质，可抑制细胞增殖，特别是癌症和与癌症相关的疾病。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，本发明的化合物可用于治疗、预防和/或抑制这些疾病。因此，本发明还包括含有这些化合物的药物配方和使用这些化合物和配方抑制癌症和治疗、预防或抑制上述疾病的方法。
• Synthesis, proapoptotic screening, and structure–activity relationships of novel aza-lupane triterpenoids
  作者：Aye Aye Mar、Erika L. Szotek、Ali Koohang、William P. Flavin、David A. Eiznhamer、Michael T. Flavin、Ze-Qi Xu

  DOI：10.1016/j.bmcl.2010.07.120

  日期：2010.9

  Apoptosis is a highly regulated process by which excessive cells are eliminated in order to maintain normal cell development and tissue homeostasis. Resistance to apoptosis often contributes to failure in cancer prevention and treatment. Apoptotic cell death regulators are considered important targets for discovery and development of new therapeutic agents in oncology research. A class of novel aza-lupane triterpenoids were designed, synthesized, and evaluated for antitumor activity against a panel of cancer cell lines of different histogenic origin and for ability to induce apoptosis. 3,30-Bis(aza) derivatives were identified not only to possess improved cytotoxicity compared to the natural product betulinic acid but also to affect cell death predominantly via apoptosis, whereas the mono(aza) derivatives apparently triggered cell death via different, non-apoptotic pathway(s). (c) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and cytotoxicity of 2-cyano-28-hydroxy-lup-1-en-3-ones
  作者：Ali Koohang、Nathan D. Majewski、Erika L. Szotek、Aye Aye Mar、David A. Eiznhamer、Michael T. Flavin、Ze-Qi Xu

  DOI：10.1016/j.bmcl.2009.02.107

  日期：2009.4

  New A-ring modified betulin and dihydrobetulin derivatives possessing the 2-cyano-1-en-3-one moiety were prepared and tested for cytotoxicity in seven cancer cell lines. The most active agent 9a synthesized in this account was further demonstrated to induce apoptosis and to activate caspases in malignant melanoma cells. (C) 2009 Elsevier Ltd. All rights reserved.