(12aR,13R)-6,7-dimethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopenta[b]triphenylene-3,13-diol | 1223487-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (12aR,13R)-6,7-dimethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopenta[b]triphenylene-3,13-diol
• 英文别名: (13aR,14R)-6,7-dimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine-3,14-diol
• CAS: 1223487-29-3
• 化学式: C₂₂H₂₃NO₄
• 分子量: 365.429
• InChiKey: SBVBOLGVLBCFIL-GCJKJVERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 10% palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (12aR,13R)-6,7-dimethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopenta[b]triphenylene-3,13-diol
  参考文献：
  名称：

  Asymmetric synthesis of phenanthroindolizidine alkaloids with hydroxyl group at the C14 position and evaluation of their antitumor activities

  摘要：

  The asymmetric total synthesis of the strongly cytotoxic phenanthroindolizidine alkaloid 3 was achieved. Using the same route, various derivatives were also synthesized. Cytotoxicity of those synthetic compounds was evaluated and compounds 19, 23, and 27 demonstrated potent cytotoxicities similar to that of 3. The in vivo antitumor efficacy of selected compounds was also evaluated and 23 demonstrated moderate antitumor efficacy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.008

文献信息

• Asymmetric synthesis of phenanthroindolizidine alkaloids with hydroxyl group at the C14 position and evaluation of their antitumor activities
  作者：Takashi Ikeda、Takashi Yaegashi、Takeshi Matsuzaki、Syusuke Hashimoto、Seigo Sawada

  DOI：10.1016/j.bmcl.2010.11.008

  日期：2011.1

  The asymmetric total synthesis of the strongly cytotoxic phenanthroindolizidine alkaloid 3 was achieved. Using the same route, various derivatives were also synthesized. Cytotoxicity of those synthetic compounds was evaluated and compounds 19, 23, and 27 demonstrated potent cytotoxicities similar to that of 3. The in vivo antitumor efficacy of selected compounds was also evaluated and 23 demonstrated moderate antitumor efficacy. (C) 2010 Elsevier Ltd. All rights reserved.