3-aminobetulinic acid | 216156-66-0

• 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-aminobetulinic acid
• 英文别名: 3-amino-3-deoxybetulinic acid；3-aminolup-20(29)-en-28-oic acid；(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-9-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid；(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-9-amino-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• CAS: 216156-66-0
• 化学式: C₃₀H₄₉NO₂
• 分子量: 455.725
• InChiKey: ZZWDPHKXZJTXKA-WXCAYEECSA-N

物化性质

• 沸点：
  541.0±33.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-aminobetulinic acid 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 以60%的产率得到(1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-amino-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
  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：

  路路通酸 在 ammonium acetate 、 氨 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以79 %的产率得到3-aminobetulinic acid
  参考文献：
  名称：

  桦木醇，桦木糖酸，3-氨基桦木酸。改进衍生物的提取和制备合成。

  摘要：

  我们优化了从白桦树皮中提取和纯化桦木醇的工艺，并改进了桦木醇最简单衍生物的制备合成，即桦木酸、桦木醛和 3-氨基桦木酸，作为后续修饰的平台。

  DOI：

  10.1007/s11172-022-3651-7

文献信息

• Synthesis of betulinic acid derivatives with activity against human melanoma
  作者：Darrick S.H.L. Kim、John M. Pezzuto、Emily Pisha

  DOI：10.1016/s0960-894x(98)00295-9

  日期：1998.7

  Betulinic acid has been modified at C-3, C-20, and C-28 positions and the toxicity of the derivatives has been evaluated against cultured human melanoma (MEL-2) and human epidermoid carcinoma of the mouth (KB) cell lines. This preliminary investigation demonstrates that simple modifications of the parent structure of betulinic acid can produce potentially important derivatives, which may be developed as antitumor drugs. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.
• [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.
• 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。
• Betulin, betulonic acid, 3-aminobetulinic acid. Improved extraction and preparative syntheses of derivatives
  作者：M. V. Kaverin、P. A. Morozova、L. V. Snegur

  DOI：10.1007/s11172-022-3651-7

  日期：2022.10

  We optimized the process of extraction and purification of betulin from birch bark and modified preparative syntheses of the simplest derivatives of betulin, namely, betulonic acid, betulonic aldehyde, and 3-aminobetulinic acid, as a platform for subsequent modifications.

  我们优化了从白桦树皮中提取和纯化桦木醇的工艺，并改进了桦木醇最简单衍生物的制备合成，即桦木酸、桦木醛和 3-氨基桦木酸，作为后续修饰的平台。