(13aS,14S)-14-(butylamino)-3,6,7-trimethoxy-12,13,13a,14-tetrahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-11(9H)-one | 1380677-90-6

• 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,14S)-14-(butylamino)-3,6,7-trimethoxy-12,13,13a,14-tetrahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-11(9H)-one
• 英文别名: (13aS,14S)-14-(butylamino)-3,6,7-trimethoxy-12,13,13a,14-tetrahydro-9H-phenanthro[9,10-f]indolizin-11-one
• CAS: 1380677-90-6
• 化学式: C₂₇H₃₂N₂O₄
• 分子量: 448.562
• InChiKey: AOQHSNORNSQRRV-WXVAWEFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (13aS,14S)-14-(butylamino)-3,6,7-trimethoxy-12,13,13a,14-tetrahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-11(9H)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到(13aS,14S)-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：

  (3,6,7-trimethoxyphenanthren-9-yl)methanol 在 草酰氯 、 三溴化磷 、 四氯化钛 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.83h， 生成 (13aS,14S)-14-(butylamino)-3,6,7-trimethoxy-12,13,13a,14-tetrahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-11(9H)-one
  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

• Design, Synthesis, Antiviral Activity, and SARs of 14-Aminophenanthroindolizidines
  作者：Ziwen Wang、Lei Wang、Shuang Ma、Yuxiu Liu、Lizhong Wang、Qingmin Wang

  DOI：10.1021/jf3013376

  日期：2012.6.13

  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.