6,7-dimethoxy-phenanthrene-9-carbaldehyde | 855603-62-2

• 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: 6,7-dimethoxy-phenanthrene-9-carbaldehyde
• 英文别名: 6,7-Dimethoxy-phenanthren-9-carbaldehyd；6,7-dimethoxyphenanthrene-9-carbaldehyde
• CAS: 855603-62-2
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: PJMRCUZVAGWUPA-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C
• 沸点：
  457.1±25.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-phenanthrene-9-carbaldehyde 在 盐酸 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 生成 2,3-dimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline
  参考文献：
  名称：

  Synthesis and structure–activity studies of antofine analogues as potential anticancer agents

  摘要：

  Due to the profound cytotoxicities and interesting biochemical aspects, phenanthroindolizidine alkaloids have received an attention as potential therapeutic leads. To define the features of the molecule that are essential for cytotoxicity, we have synthesized and evaluated a series of phenanthroindolizidine alkaloid, antofine, analogues with different substituents on the phenanthrene ring. The systematic structure activity relationship studies elucidate the essential functional group requirement of phenanthrene ring, providing the basis for further development of phenanthroindolizidine alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.080
• 作为产物：
  描述：

  9-cyano-6,7-dimethoxyphenanthrene 在 二异丁基氢化铝 、 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以78%的产率得到6,7-dimethoxy-phenanthrene-9-carbaldehyde
  参考文献：
  名称：

  PHENANTHROINDOLIZIDINE DERIVATIVE AND NF kB INHIBITOR CONTAINING SAME AS ACTIVE INGREDIENT

  摘要：

  公开号：

  EP2351753B1

文献信息

• PHENANTHROINDOLIZIDINE DERIVATIVE AND NF kB INHIBITOR CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：Kabushiki Kaisha Yakult Honsha

  公开号：EP2351753B1

  公开（公告）日：2015-02-11
• 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.
• Synthesis and structure–activity studies of antofine analogues as potential anticancer agents
  作者：Ye Fu、Sang Kook Lee、Hye-Young Min、Taeho Lee、Jaekwang Lee、Maosheng Cheng、Sanghee Kim

  DOI：10.1016/j.bmcl.2006.09.080

  日期：2007.1

  Due to the profound cytotoxicities and interesting biochemical aspects, phenanthroindolizidine alkaloids have received an attention as potential therapeutic leads. To define the features of the molecule that are essential for cytotoxicity, we have synthesized and evaluated a series of phenanthroindolizidine alkaloid, antofine, analogues with different substituents on the phenanthrene ring. The systematic structure activity relationship studies elucidate the essential functional group requirement of phenanthrene ring, providing the basis for further development of phenanthroindolizidine alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.