22β-benzoyloxy-3-oxo-olean-12-en-28-oic acid | 67991-49-5

• 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: 22β-benzoyloxy-3-oxo-olean-12-en-28-oic acid
• 英文别名: (4R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)-4-benzoyloxy-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-carboxylic acid
• CAS: 67991-49-5
• 化学式: C₃₇H₅₀O₅
• 分子量: 574.801
• InChiKey: LVUITJIRGWGGRG-YNZRGXEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  diphenylmethyl 22β-benzoyloxy-3-oxoolean-12-en-28-oate 在 苯甲醚 、 三氟乙酸 作用下， 反应 0.08h， 以59%的产率得到22β-benzoyloxy-3-oxo-olean-12-en-28-oic acid
  参考文献：
  名称：

  Lantadenes and Their Esters as Potential Antitumor Agents

  摘要：

  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.

  DOI：

  10.1021/np800167x

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.