(1R,4R,5R,8R,14R,15R,18R,19R,20R)-4,5,9,9,14,21,21-heptamethyl-10,25-dioxahexacyclo[18.3.2.01,19.04,18.05,15.08,14]pentacosan-11-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,4R,5R,8R,14R,15R,18R,19R,20R)-4,5,9,9,14,21,21-heptamethyl-10,25-dioxahexacyclo[18.3.2.01,19.04,18.05,15.08,14]pentacosan-11-one
• 化学式: C₃₀H₄₈O₃
• 分子量: 456.709
• InChiKey: VAPKIVYIZQDLCT-CCJYTWKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  33
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4R,5R,8R,14R,15R,18R,19R,20R)-4,5,9,9,14,21,21-heptamethyl-10,25-dioxahexacyclo[18.3.2.01,19.04,18.05,15.08,14]pentacosan-11-one 在 硫酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 264.0h， 以85%的产率得到methyl 3-((4R,4aS,4bR,6aR,7R,8R,10aR,10bR,12aR)-8-(2-hydroxypropan-2-yl)-3,3,7,10a,10b-pentamethylhexadecahydro-1H-4,12a-(epoxymethano)chrysen-7-yl)propanoate
  参考文献：
  名称：

  Sejbal, Jan; Klinot, Jiri; Vystrcil, Alois, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 4, p. 1052 - 1061

  摘要：

  DOI：
• 作为产物：
  描述：

  白桦脂醇 在 Jones reagent 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 生成 (1R,4R,5R,8R,14R,15R,18R,19R,20R)-4,5,9,9,14,21,21-heptamethyl-10,25-dioxahexacyclo[18.3.2.01,19.04,18.05,15.08,14]pentacosan-11-one
  参考文献：
  名称：

  Simple structural modifications confer cytotoxicity to allobetulin

  摘要：

  A variety of allobetulin derivatives was synthesized from allobetulin or allobetulone. These compounds were screened for their cytotoxic activity using a photometric SRB assay employing six different human tumor cell lines. In summary, opening of ring A of allobetulin in general lowers the cytotoxicity, but the 2,3-seco diethyl ester was highly cytotoxic and remarkable selective for A549 lung carcinoma cells while being significantly less cytotoxic for non-malignant mouse fibroblasts. The introduction of an amino group at position C-3 in the allobetulin skeleton enhances cytotoxicity and furnishes highly cytotoxic compounds. Their selectivity to distinguish between cancer cell and non-malignant cell depends on the configuration at position C-3. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.015

文献信息

• Simple structural modifications confer cytotoxicity to allobetulin
  作者：Lucie Heller、Anja Obernauer、René Csuk

  DOI：10.1016/j.bmc.2015.05.015

  日期：2015.7

  A variety of allobetulin derivatives was synthesized from allobetulin or allobetulone. These compounds were screened for their cytotoxic activity using a photometric SRB assay employing six different human tumor cell lines. In summary, opening of ring A of allobetulin in general lowers the cytotoxicity, but the 2,3-seco diethyl ester was highly cytotoxic and remarkable selective for A549 lung carcinoma cells while being significantly less cytotoxic for non-malignant mouse fibroblasts. The introduction of an amino group at position C-3 in the allobetulin skeleton enhances cytotoxicity and furnishes highly cytotoxic compounds. Their selectivity to distinguish between cancer cell and non-malignant cell depends on the configuration at position C-3. (C) 2015 Elsevier Ltd. All rights reserved.
• Sejbal, Jan; Klinot, Jiri; Vystrcil, Alois, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 4, p. 1052 - 1061
  作者：Sejbal, Jan、Klinot, Jiri、Vystrcil, Alois

  DOI：——

  日期：——