(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-[3-[2-(4-hydroxyphenyl)ethylamino]prop-1-en-2-yl]-5a,5b,8,8,11a-pentamethyl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one | 1115434-69-9

• 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: (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-[3-[2-(4-hydroxyphenyl)ethylamino]prop-1-en-2-yl]-5a,5b,8,8,11a-pentamethyl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
• CAS: 1115434-69-9
• 化学式: C₃₈H₅₇NO₃
• 分子量: 575.875
• InChiKey: PANRNQMMBRCNTO-UJTBAKDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-[3-[2-(4-hydroxyphenyl)ethylamino]prop-1-en-2-yl]-5a,5b,8,8,11a-pentamethyl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one 在 sodium tetrahydroborate 作用下， 生成 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-[3-[2-(4-hydroxyphenyl)ethylamino]prop-1-en-2-yl]-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
  参考文献：
  名称：

  Synthesis, proapoptotic screening, and structure–activity relationships of novel aza-lupane triterpenoids

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.07.120
• 作为产物：
  描述：

  (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-1-[3-[2-(4-hydroxyphenyl)ethylamino]prop-1-en-2-yl]-5a,5b,8,8,11a-pentamethyl-3a-(oxan-2-yloxymethyl)-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 生成 (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-[3-[2-(4-hydroxyphenyl)ethylamino]prop-1-en-2-yl]-5a,5b,8,8,11a-pentamethyl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
  参考文献：
  名称：

  Synthesis, proapoptotic screening, and structure–activity relationships of novel aza-lupane triterpenoids

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.07.120

文献信息

• 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.