(2R)-1-{[3-(benzyloxy)-6,7-dimethoxy-9-phenanthryl]methyl}-5-oxopyrrolidine-2-carboxylic acid | 1223487-20-4

• 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: (2R)-1-{[3-(benzyloxy)-6,7-dimethoxy-9-phenanthryl]methyl}-5-oxopyrrolidine-2-carboxylic acid
• 英文别名: (2R)-1-[(6,7-dimethoxy-3-phenylmethoxyphenanthren-9-yl)methyl]-5-oxopyrrolidine-2-carboxylic acid
• CAS: 1223487-20-4
• 化学式: C₂₉H₂₇NO₆
• 分子量: 485.536
• InChiKey: FUSWLACKOCVVMO-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-1-{[3-(benzyloxy)-6,7-dimethoxy-9-phenanthryl]methyl}-5-oxopyrrolidine-2-carboxylic acid 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 草酰氯 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 18.25h， 生成 3-O-desmethyl-13a-(R)-deoxytylophorinine
  参考文献：
  名称：

  Stereospecific Synthesis and Biological Evaluation of Monodesmethyl Metabolites of (+)-13a-(S)-Deoxytylophorinine as Potential Antitumor Agents

  摘要：

  Three major monodesmethyl metabolites of (+)-13a-(S)-deoxytylophorinine were synthesized stereospecifically and their configurations at C-13a were determined. Biological assays revealed that one of the metabolites, 3-O-desmethyl-13a-(S)-deoxytylophorinine, had a higher cytotoxic potency than the parent compound or the positive controls doxorubicin (Adriamycin) and paclitaxel (Taxol).

  DOI：

  10.1055/s-0032-1316810
• 作为产物：
  描述：

  [3-(benzyloxy)-6,7-dimethoxy-9-phenanthryl]methanol 在 水 、 三氟乙酸 、 sodium iodide 作用下， 以 1,4-二氧六环 、 丙酮 、 乙腈 为溶剂， 反应 21.5h， 生成 (2R)-1-{[3-(benzyloxy)-6,7-dimethoxy-9-phenanthryl]methyl}-5-oxopyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Stereospecific Synthesis and Biological Evaluation of Monodesmethyl Metabolites of (+)-13a-(S)-Deoxytylophorinine as Potential Antitumor Agents

  摘要：

  Three major monodesmethyl metabolites of (+)-13a-(S)-deoxytylophorinine were synthesized stereospecifically and their configurations at C-13a were determined. Biological assays revealed that one of the metabolites, 3-O-desmethyl-13a-(S)-deoxytylophorinine, had a higher cytotoxic potency than the parent compound or the positive controls doxorubicin (Adriamycin) and paclitaxel (Taxol).

  DOI：

  10.1055/s-0032-1316810

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.