methyl 22β-hydroxy-3-oxoolean-12-en-28-oate | 51181-33-0

• 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: methyl 22β-hydroxy-3-oxoolean-12-en-28-oate
• 英文别名: methyl 22β-hydroxy-3-oxo-olean-12-en-28-ate；methyl 22β-hydroxy-3-oxoolean-12-en-28-onate；22β-hydroxy-3-oxo-olean-12-en-28-oic acid methyl ester；22β-Hydroxy-3-oxo-olean-12-en-28-saeure-methylester；methyl (4R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)-4-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylate
• CAS: 51181-33-0
• 化学式: C₃₁H₄₈O₄
• 分子量: 484.72
• InChiKey: SKHZDCVXZQISSR-GUMDXBKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 22β-hydroxy-3-oxoolean-12-en-28-oate 在 chromium(VI) oxide 作用下， 生成 Methyl-3.22-dioxoolean-12-en-18-oat
  参考文献：
  名称：

  Barton et al., Journal of the Chemical Society, 1954, p. 903,906

  摘要：

  DOI：
• 作为产物：
  描述：

  lantadene A 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 3.0h， 生成 methyl 22β-hydroxy-3-oxoolean-12-en-28-oate
  参考文献：
  名称：

  Johns, Stanley R.; Lamberton, John A.; Morton, Trevor C., Australian Journal of Chemistry, 1983, vol. 36, # 9, p. 1895 - 1902

  摘要：

  DOI：

文献信息

• Novel lung adenocarcinoma and nuclear factor-kappa B (NF-κB) inhibitors: Synthesis and evaluation of lantadene congeners
  作者：Sharad Kumar Suthar、Hong L. Boon、Manu Sharma

  DOI：10.1016/j.ejmech.2013.12.052

  日期：2014.3

  The C-3, C-17 and C-22 congeners of pentacyclic triterpenoids reduced lantadene A (3), B (4) and 22 beta hydroxyoleanolic acid (5) were synthesized and were tested in vitro for their NF-kappa B and IKK beta inhibitory potencies and cytotoxicity against A549 lung cancer cells. The lead congeners 12 and 13 showed IC50 of 0.56 and 0.42 mu mol, respectively against TNF-alpha. induced activation of NF-kappa B. The congeners 12 and 13 exhibited inhibition of IKK beta in a single-digit micromolar dose and at the same time, 12 and 13 showed marked cytotoxicity against A549 lung cancer cells with IC50 of 0.12 and 0.08 mu mol, respectively. The lead ester congeners were stable in the acidic pH, while hydrolyzed readily in the human blood plasma to release the active parent moieties. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Lantadenes and Their Esters as Potential Antitumor Agents
  作者：M. Sharma、P. D. Sharma、M. P. Bansal

  DOI：10.1021/np800167x

  日期：2008.7.1

  Lantadenes are pentacyclic triterpenoids of the weed Lantana camara. Five new lantadenes (14-18) and their methyl esters (20-24) were synthesized, characterized, and screened for cytotoxicity against four human cancer cell lines. The parent compound (1) and the four most active compounds (15, 16, 21, and 22) were further studied for their in vivo tumor inhibitory potential on squamous cell carcinogenesis in Swiss albino mice induced by 7,12-dimethylbenz[a]anthracene (DMBA) and promoted by 12-O-tetradecanoylphorbol-13-acetate (TPA). These results were supported by histopathological studies and discussed in terms of structure-activity relationships. The results inferred the importance of the groups attached to C-22 and C-17 in relation to the antitumor activity of these compounds.
• Barton et al., Journal of the Chemical Society, 1954, p. 903,906
  作者：Barton et al.

  DOI：——

  日期：——
• Johns, Stanley R.; Lamberton, John A.; Morton, Trevor C., Australian Journal of Chemistry, 1983, vol. 36, # 9, p. 1895 - 1902
  作者：Johns, Stanley R.、Lamberton, John A.、Morton, Trevor C.、Suares, Hector、Willing, Richard I.

  DOI：——

  日期：——