(2S)-1-(10-bromo-2,3,6,7-tetramethoxyphenanthren-9-ylmethyl)-pyrrolidine-2-carboxylic acid methyl ester | 1225041-52-0

• 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: (2S)-1-(10-bromo-2,3,6,7-tetramethoxyphenanthren-9-ylmethyl)-pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: (S)-methyl 1-[(9-bromo-2,3,6,7-tetramethoxyphenanthren-10-yl)methyl]pyrrolidine-2-carboxylate；methyl (2S)-1-[(10-bromo-2,3,6,7-tetramethoxyphenanthren-9-yl)methyl]pyrrolidine-2-carboxylate
• CAS: 1225041-52-0
• 化学式: C₂₅H₂₈BrNO₆
• 分子量: 518.404
• InChiKey: FPIGYYFAUCYJGU-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-1-(10-bromo-2,3,6,7-tetramethoxyphenanthren-9-ylmethyl)-pyrrolidine-2-carboxylic acid methyl ester 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 生成 (S)-1-((10-bromo-2,3,6,7-tetramethoxyphenanthren-9-yl)methyl)pyrrolidine-2-carbaldehyde
  参考文献：
  名称：

  自由基环化由l-脯氨酸无消旋地合成（S）-（+）-酪氨酸

  摘要：

  从1-脯氨酸以九个线性步骤合成了菲咯啉吲哚并烷生物碱（S）-（+）-酪氨酸，该步骤包括双溴化和N-叠氮基嘧啶的自由基环化作为关键步骤。菲部分是由高veraveratric酸和veratraldehyde制备的，并允许每个氧取代的环发生变化。

  DOI：

  10.1021/ol100652b
• 作为产物：
  描述：

  9-bromo-10-(bromomethyl)-2,3,6,7-tetramethoxyphenanthrene 、 L-脯氨酸甲酯盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以92%的产率得到(2S)-1-(10-bromo-2,3,6,7-tetramethoxyphenanthren-9-ylmethyl)-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  自由基环化由l-脯氨酸无消旋地合成（S）-（+）-酪氨酸

  摘要：

  从1-脯氨酸以九个线性步骤合成了菲咯啉吲哚并烷生物碱（S）-（+）-酪氨酸，该步骤包括双溴化和N-叠氮基嘧啶的自由基环化作为关键步骤。菲部分是由高veraveratric酸和veratraldehyde制备的，并允许每个氧取代的环发生变化。

  DOI：

  10.1021/ol100652b

文献信息

• Racemization-Free Synthesis of (<i>S</i>)-(+)-Tylophorine from <scp>l</scp>-Proline by Radical Cyclization
  作者：Alexander Stoye、Till Opatz

  DOI：10.1021/ol100652b

  日期：2010.5.7

  The phenanthroindolizidine alkaloid (S)-(+)-tylophorine was synthesized from l-proline in nine linear steps including a double bromination and a free-radical cyclization of an N-aziridinylimine as the key steps. The phenanthrene moiety was prepared from homoveratric acid and veratraldehyde and permits the variation of each oxygen-substituted ring.

  从1-脯氨酸以九个线性步骤合成了菲咯啉吲哚并烷生物碱（S）-（+）-酪氨酸，该步骤包括双溴化和N-叠氮基嘧啶的自由基环化作为关键步骤。菲部分是由高veraveratric酸和veratraldehyde制备的，并允许每个氧取代的环发生变化。
• Design, Synthesis, and Anti-tobacco Mosaic Virus (TMV) Activity of Phenanthroindolizidines and Their Analogues
  作者：Ziwen Wang、Peng Wei、Lizhong Wang、Qingmin Wang

  DOI：10.1021/jf303550a

  日期：2012.10.17

  On the basis of our previous structure-activity relationship (SAR) and antiviral mechanism studies, a series of phenanthroindolizidines and their analogues 3-20 were designed, targeting tobacco mosaic virus (TMV) RNA, synthesized, and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds displayed good anti-TMV activity, and some of them exhibited higher antiviral activity than that of commercial Ningnanmycin (perhaps the most successful registered antiplant viral agent). Especially, (S)-deoxytylophorinine (5) with excellent anti-TMV activity (inactivation activity, 59.8%/500 mu g mL(-1) and 40.3%/100 mu g mL(-1); curative activity, 65.1%/500 mu g mL(-1) and 43.7%/100 mu g mL(-1); and protection activity, 70.2%/500 mu g mL(-1) and 51.3%/100 mu g mL(-1)) emerged as a potential inhibitor of the plant virus. Compound 20 exhibited a strong in vivo protection effect against TMV at 100 mu g mL(-1), which indicated that phenanthroindolizidine analogues with a seven-membered D ring have a new and interesting structural scaffold and have great potential for further development as tobacco protection agents.