messagenic acid D | 132473-93-9

• 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: messagenic acid D
• 英文别名: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-hydroxy-1-(3-hydroxyprop-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]chrysene-3a-carboxylic acid
• CAS: 132473-93-9
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: NILZYBMKKVCAHD-FZFNOLFKSA-N

物化性质

• 沸点：
  588.6±30.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  白桦脂酸 在 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以8 mg的产率得到messagenic acid D
  参考文献：
  名称：

  来自 Leptospermum scoparium 的三种羽扇豆衍生物

  摘要：

  Leptospermum scoparium 栽培品种地上部分的乙醚提取物产生具有 20,29,30-trinorlupane 骨架的内酯 (1)。此外，分离出 2α-羟基熊果酸 (2)、铂酸 (3) 和 3β, 30-二羟基-lup-20 (29)-烯-28-油酸 (4)。

  DOI：

  10.1002/ardp.19963291005

文献信息

• Method of preparing and use of prodrugs of betulinic acid derivatives
  申请人：Pezzuto M. John

  公开号：US20070072835A1

  公开（公告）日：2007-03-29

  A composition and method of preventing or inhibiting tumor growth and, more particularly, of treating a malignant tumor, using prodrugs of plant-derived compounds and derivatives is disclosed. In the method, a composition containing betulinic acid or a betulinic acid derivative is administered in a prodrug form to release betulinic acid or a betulinic acid derivative in vivo at the tumor site.

  本发明涉及一种预防或抑制肿瘤生长的组合物和方法，更具体地，涉及使用植物衍生物和衍生物的前药来治疗恶性肿瘤。在该方法中，含有苦杏酸或苦杏酸衍生物的组合物以前药形式给予，以在体内肿瘤部位释放苦杏酸或苦杏酸衍生物。
• 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。
• Development of C-20 modified betulinic acid derivatives as antitumor agents
  作者：Jin Yung Kim、Han-Mo Koo、Darrick S.H.L Kim

  DOI：10.1016/s0960-894x(01)00460-7

  日期：2001.9

  Chemical modifications were performed on C-20 position of betulinic acid for a structure-activity relationship study. The evaluation of the compounds using human colon carcinoma HCT-116, human prostate adenocarcinoma PC3, and human melanoma cell lines M14-MEL, SK-MEL-2, and UACC-257 did not show any selective cytotoxicity towards melanoma cells. The results from both MTT reduction assay and SRB staining assay were comparable that no remarkable differences in cytotoxicity profile of the compounds were noticed. The C-20 position was found to be sensitive to the size and the electron density of the substituents in retaining the cytotoxicity of betulinic acid and was found to be undesirable position to derivatize. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Allylic Hydroxylation Through Acid Catalysed Epoxy Ring Opening of Betulinic Acid Derivatives
  作者：Swapan Pramanick、Suparna Mandal、Sibabrata Mukhopadhyay、Sailen Jha

  DOI：10.1080/00397910500180568

  日期：2005.8.1

  Acid catalysed epoxy ring opening of several lupane type triterpenoids leads to unusual allylic hydroxylation. The reaction involves the formation of epoxide by m-chloroperbenzoic acid followed by the treatment of mineral acid. The simple methodology finds utility to introduce a hydroxyl function at the allylic position in these triterpenoids, which is otherwise quite difficult.
• [EN] LUPANE-TYPE TRITERPENOIDS MODIFIED AT 30-POSITION AND ANALOGUES THEREOF<br/>[FR] TRITERPÉNOÏDES DE TYPE LUPANE MODIFIÉS EN POSITION 30 ET LEURS ANALOGUES
  申请人：ADVANCED LIFE SCIENCES INC

  公开号：WO2009020732A1

  公开（公告）日：2009-02-12

  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.