(1S,3aS,5aR,5bR,7aR,12aR,12bR,14aR,14bR)-1-isopropyl-5a,5b,8,8,12a-pentamethyl-3a-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2,3,3a,4,5,5a,5b,6,7,7a,8,12,12a,12b,13,14,14a,14b-octadecahydro-1H-cyclopenta[7,8]chryseno[3,2-d]isoxazole | 951132-04-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (1S,3aS,5aR,5bR,7aR,12aR,12bR,14aR,14bR)-1-isopropyl-5a,5b,8,8,12a-pentamethyl-3a-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2,3,3a,4,5,5a,5b,6,7,7a,8,12,12a,12b,13,14,14a,14b-octadecahydro-1H-cyclopenta[7,8]chryseno[3,2-d]isoxazole
• 英文别名: (1R,2R,10R,13R,14R,17S,20S,21R,22R)-2,9,9,13,14-pentamethyl-17-(oxan-2-yloxymethyl)-20-propan-2-yl-7-oxa-6-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-4(8),5-diene
• CAS: 951132-04-0
• 化学式: C₃₆H₅₇NO₃
• 分子量: 551.853
• InChiKey: QSZXFFPXESOTBB-XIYJGOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3aS,5aR,5bR,7aR,12aR,12bR,14aR,14bR)-1-isopropyl-5a,5b,8,8,12a-pentamethyl-3a-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2,3,3a,4,5,5a,5b,6,7,7a,8,12,12a,12b,13,14,14a,14b-octadecahydro-1H-cyclopenta[7,8]chryseno[3,2-d]isoxazole 在 sodium methylate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.0h， 以90%的产率得到ALS 845
  参考文献：
  名称：

  Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin

  摘要：

  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。

  公开号：

  US20070232577A1
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 ALS 778 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到(1S,3aS,5aR,5bR,7aR,12aR,12bR,14aR,14bR)-1-isopropyl-5a,5b,8,8,12a-pentamethyl-3a-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2,3,3a,4,5,5a,5b,6,7,7a,8,12,12a,12b,13,14,14a,14b-octadecahydro-1H-cyclopenta[7,8]chryseno[3,2-d]isoxazole
  参考文献：
  名称：

  Synthesis and cytotoxicity of 2-cyano-28-hydroxy-lup-1-en-3-ones

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.02.107

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。
• [EN] SYNTHETIC PENTACYCLIC TRITERPENOIDS AND DERIVATIVES OF BETULINIC ACID AND BETULIN<br/>[FR] TRITERPENOIDES PENTACYCLIQUES SYNTHETIQUES ET DERIVES D'ACIDE BETULINIQUE ET DE BETULINE
  申请人：ADVANCED LIFE SCIENCES INC

  公开号：WO2007112043A2

  公开（公告）日：2007-10-04

  [EN] 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.
  [FR] La présente invention concerne des inhibiteurs à petite molécule d'affections de la prolifération cellulaire, en particulier du cancer et des affections associées au cancer. Par exemple, les malignités associées incluent le cancer de l'ovaire, le cancer du col de l'utérus, le cancer du sein, le cancer colorectal et les glioblastomes, entre autres. Les composés de la présente invention sont par conséquent utiles pour le traitement, la prévention et/ou l'inhibition de ces maladies. Ainsi, la présente invention concerne également des formulations pharmaceutiques comprenant ces composés, et les procédés d'utilisation des composés et des formulations afin d'inhiber le cancer et traiter, prévenir, ou inhiber les maladies susmentionnées.
• 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.