ent-3-氧代贝壳烯烷-16,17-二醇 | 135683-73-7

• 物质功能分类: 天然产物 - 萜类
• 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
• 中文名称: ent-3-氧代贝壳烯烷-16,17-二醇
• 英文名称: ent-16α,17-dihydroxykauran-3-one
• 英文别名: ent-16S,17-dihydroxy-kaurane-3-one；ent-kaurane-3-oxo-16β,17-diol；ent-16S,17-Dihydroxykauran-3-one；(1S,4S,9S,10R,13R,14S)-14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecan-6-one
• CAS: 135683-73-7
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: MPDUJZZNNBJFAB-XYYNDNLRSA-N

物化性质

• 沸点：
  460.0±40.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ent-3-氧代贝壳烯烷-16,17-二醇 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 以7 mg的产率得到17-acetoxy-16β-hydroxy-3-oxo-ent-kaurane
  参考文献：
  名称：

  Antitumor activity of terpenoids against classical and atypical multidrug resistant cancer cells

  摘要：

  Nineteen terpenoids, including macrocyclic diterpenes, diterpenic lactones and other polycyclic diterpenes, steroids and a triterpene isolated from the methanolic extracts of Euphorbia species, were evaluated for their potential antineoplastic activity in various human cancer cell lines that were derived from three tumor entities gastric (EPG85-257). pancreatic (EPP85-181) and colon (HT-29) carcinomas Furthermore, different multidrug-resistant variants of these cancer cell lines with over-expression of MDR1/P-gp or no MDR1/P-gp expression were also investigated In parental drug-sensitive cell lines, the tested compounds showed a moderate/weak antiproliferative effect or were inactive. Most of them were found more effective in drug-resistant cells than in the parental, drug-sensitive ones, and some of them showed high antineoplastic efficacy in classical or atypical drug-resistant cells. The most active compounds were the lathyrane diterpenes latilagascenes C and D. and the diterpenic lactones 3 beta-acetoxy-helioscopinolide B and helioscopinolide E which exhibited high antineoplastic activities against the drug-resistant subline EPG85-257RDB derived from gastric carcinoma In addition, the macrocyclic lathyrane diterpene jolkinol B was found to be highly effective in the multidrug-resistant variant HT-29RNOV. (C) 2009 Elsevier GmbH. All rights reserved.

  DOI：

  10.1016/j.phymed.2009.07.009