(13aS)-3,6,7-trimethoxy-9,12,13,13a-tetrahydrophenanthro[9,10-f]indolizine-11,14-dione | 1242341-15-6

• 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: (13aS)-3,6,7-trimethoxy-9,12,13,13a-tetrahydrophenanthro[9,10-f]indolizine-11,14-dione
• CAS: 1242341-15-6
• 化学式: C₂₃H₂₁NO₅
• 分子量: 391.423
• InChiKey: IGZXGZPIJDDOHC-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (13aS)-3,6,7-trimethoxy-9,12,13,13a-tetrahydrophenanthro[9,10-f]indolizine-11,14-dione 在 lithium aluminium tetrahydride 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (13aS,14R)-N-butyl-3,6,7-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-14-amine
  参考文献：
  名称：

  Design, Synthesis, Antiviral Activity, and SARs of 14-Aminophenanthroindolizidines

  摘要：

  Based on our previous structure activity relationship and antiviral mechanism studies, a series of 14-aminophenanthroindolizidines (1a-i, 2, and 3) were designed, targeting tobacco mosaic virus (TMV) RNA, and synthesized and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds exhibited good to excellent in vivo anti-TMV activity, of which compounds Id and 1h displayed significantly higher activity than commercial ningnanmycin, and thus emerged as potential inhibitors of plant virus. The introduction of amino groups at the 14-position of phenanthroindolizidines, which is proposed to interact with arginine residues around the TMV RNA, increased anti-TMV activity.

  DOI：

  10.1021/jf3013376
• 作为产物：
  描述：

  (S)-N-[(2,3,6-trimethoxy-10-phenanthryl)methyl]pyroglutamic acid 在 草酰氯 、 N,N-二甲基甲酰胺 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到(13aS)-3,6,7-trimethoxy-9,12,13,13a-tetrahydrophenanthro[9,10-f]indolizine-11,14-dione
  参考文献：
  名称：

  Design, Synthesis, Antiviral Activity, and SARs of 14-Aminophenanthroindolizidines

  摘要：

  Based on our previous structure activity relationship and antiviral mechanism studies, a series of 14-aminophenanthroindolizidines (1a-i, 2, and 3) were designed, targeting tobacco mosaic virus (TMV) RNA, and synthesized and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds exhibited good to excellent in vivo anti-TMV activity, of which compounds Id and 1h displayed significantly higher activity than commercial ningnanmycin, and thus emerged as potential inhibitors of plant virus. The introduction of amino groups at the 14-position of phenanthroindolizidines, which is proposed to interact with arginine residues around the TMV RNA, increased anti-TMV activity.

  DOI：

  10.1021/jf3013376

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.