benzyl 3-oxo-23-hydroxy-lup-20(29)-en-28-oic acid | 136684-40-7

• 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: benzyl 3-oxo-23-hydroxy-lup-20(29)-en-28-oic acid
• 英文别名: 3-oxo-23-hydroxy-lup-20(29)-en-28-oic acid；3-oxo-23-hydroxybetulinic acid；pulsatillic acid；23-hydroxybetulonic acid；23-hydroxy-3-oxo-20(29)-lupen-28-oic acid；(1R,3aS,5aR,5bR,7aR,8R,11aR,11bR,13aR,13bR)-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
• CAS: 136684-40-7
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: FRBHXYYJMYBCSK-SECHYRITSA-N

物化性质

• 沸点：
  584.2±25.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 3-oxo-23-hydroxy-lup-20(29)-en-28-oic acid 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到23-hydroxybetulinic acid
  参考文献：
  名称：

  以桦木酸为原料部分合成 23-羟基桦木酸和 23-羟基桦木酸

  摘要：

  以天然丰富的桦木酸为原料，部分合成了具有生物活性的 23-羟基桦木酸和 23-羟基桦木酸，其中关键步骤是从桦木酸的 3-one 肟中对 23-甲基进行鲍德温环钯化，一种重要的中药。

  DOI：

  10.3184/174751912x13332875186150
• 作为产物：
  描述：

  23-hydroxybetulinic acid 在 aluminum tri-tert-butoxide 、 丙酮 作用下， 以 苯 为溶剂， 反应 1.0h， 以50 mg的产率得到benzyl 3-oxo-23-hydroxy-lup-20(29)-en-28-oic acid
  参考文献：
  名称：

  白头翁三萜类化合物

  摘要：

  从白头翁的根中分离出一种新的羽扇豆型三萜酸白头翁酸和两种新的羽扇豆素型三萜糖苷白头翁苷A和B，以及已知的23-羟基桦木酸。它们的结构特征为 3-oxo-23-hydroxy-lup-20(29)-en-28-oic acid, 3 beta, 23-dihydroxy-lup-20(29)-en-28-oic acid 3-O -alpha-L-arabinopyranoside 和 3 beta, 23-dihydroxy-lup-20(29)-en-28-oic acid 28-O-beta-D-glupyranosyl-(1-->6)-beta-D-glucopyranoside基于水解和光谱证据，包括二维中继 HOHAHA、一维多重中继 COZY 和 ROESY NMR 技术。Pulsatillic acid 对 P-388、Lewis 肺癌和人类大细胞肺癌表现出细胞毒活性。

  DOI：

  10.1016/0031-9422(96)00043-x

文献信息

• 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。
• Synthesis and antitumor activity of novel 3-oxo-23-hydroxybetulinic acid derivatives
  作者：Hengyuan Zhang、Peiqing Zhu、Jie Liu、Xue Yang、Shengtao Xu、Hequan Yao、Jieyun Jiang、Wencai Ye、Xiaoming Wu、Jinyi Xu

  DOI：10.1016/j.ejmech.2014.09.058

  日期：2014.11

  A series of novel derivatives of 3-oxo-23-hydroxybetulinic acid was designed, synthesized, and evaluated for their antiproliferative activity against a panel of cancer cell lines (HL-60, BEL-7402, SF-763, HeLa, 816 and A375). The results indicated that majority of the derivatives exhibited more significant antitumor activity than the parent compound. In particular compound 10e showed the most potent activity with IC50 values of 5.85, 6.23 and 7.22 mu M against B16, SF-763 and BEL-7402 cells, respectively. Furthermore, 10e inhibited tumor growth by 51.8% and 62.7% (w/w) in H22 and B16 xenograft mouse models, comparable to cyclophosphamide and 5-fluorouracil, respectively. (C) 2014 Elsevier Masson SAS. All rights reserved.
• WO2008/138200
  申请人：——

  公开号：——

  公开（公告）日：——
• A Partial Synthesis of 23-Hydroxybetulonic Acid and 23-Hydroxybetulinic Acid Starting from Betulinic Acid
  作者：Fei Sun、Peiqing Zhu、Hequan Yao、Xiaoming Wu、Jinyi Xu

  DOI：10.3184/174751912x13332875186150

  日期：2012.5

  active 23-hydroxybetulonic acid and 23-hydroxybetulinic acid starting from the naturally abundant betulinic acid has been developed in which the key step was the Baldwin's cyclopalladation of the 23-methyl group from a 3-one oxime of betulinic acid, an important drug in Chinese medicine.

  以天然丰富的桦木酸为原料，部分合成了具有生物活性的 23-羟基桦木酸和 23-羟基桦木酸，其中关键步骤是从桦木酸的 3-one 肟中对 23-甲基进行鲍德温环钯化，一种重要的中药。
• Triterpenoids from Pulsatilla chinensis
  作者：Wen-Cai Ye、Nine-Ning Ji、Shou-Xun Zhao、Jing-Han Liu、Tao Ye、M.A. McKervey、P. Stevenson

  DOI：10.1016/0031-9422(96)00043-x

  日期：1996.6

  triterpenic acid, pulsatillic acid, and two new lupane type triterpenoid glycosides, pulsatilloside A and B, along with the known 23-hydroxybetulinic acid were isolated from the roots of Pulsatilla chinensis. Their structures were characterized as 3-oxo-23-hydroxy-lup-20(29)-en-28-oic acid, 3 beta, 23-dihydroxy-lup-20(29)-en-28-oic acid 3-O-alpha-L-arabinopyranoside and 3 beta, 23-dihydroxy-lup-20(29)-en-28-oic

  从白头翁的根中分离出一种新的羽扇豆型三萜酸白头翁酸和两种新的羽扇豆素型三萜糖苷白头翁苷A和B，以及已知的23-羟基桦木酸。它们的结构特征为 3-oxo-23-hydroxy-lup-20(29)-en-28-oic acid, 3 beta, 23-dihydroxy-lup-20(29)-en-28-oic acid 3-O -alpha-L-arabinopyranoside 和 3 beta, 23-dihydroxy-lup-20(29)-en-28-oic acid 28-O-beta-D-glupyranosyl-(1-->6)-beta-D-glucopyranoside基于水解和光谱证据，包括二维中继 HOHAHA、一维多重中继 COZY 和 ROESY NMR 技术。Pulsatillic acid 对 P-388、Lewis 肺癌和人类大细胞肺癌表现出细胞毒活性。