(S)-1-[(9-bromo-2,3,6,7-tetramethoxyphenanthren-10-yl)methyl]pyrrolidine-2-carboxylic acid | 1394286-35-1

• 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: (S)-1-[(9-bromo-2,3,6,7-tetramethoxyphenanthren-10-yl)methyl]pyrrolidine-2-carboxylic acid
• 英文别名: (2S)-1-[(10-bromo-2,3,6,7-tetramethoxyphenanthren-9-yl)methyl]pyrrolidine-2-carboxylic acid
• CAS: 1394286-35-1
• 化学式: C₂₄H₂₆BrNO₆
• 分子量: 504.378
• InChiKey: YNVAYGQUMNRHPT-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-1-[(9-bromo-2,3,6,7-tetramethoxyphenanthren-10-yl)methyl]pyrrolidine-2-carboxylic acid 在 三乙基硅烷 、 sodium tetrahydroborate 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 甲醇 、 三氟乙酸 为溶剂， 反应 23.0h， 生成 (S)-9,11,12,13,13a,14-六氢-2,3,6,7-四甲氧基二苯并[f,h]吡咯并(1,2-b)异喹啉
  参考文献：
  名称：

  Design, Synthesis, and Anti-tobacco Mosaic Virus (TMV) Activity of Phenanthroindolizidines and Their Analogues

  摘要：

  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.

  DOI：

  10.1021/jf303550a
• 作为产物：
  描述：

  9-bromo-10-(bromomethyl)-2,3,6,7-tetramethoxyphenanthrene 在 水 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 (S)-1-[(9-bromo-2,3,6,7-tetramethoxyphenanthren-10-yl)methyl]pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Design, Synthesis, and Anti-tobacco Mosaic Virus (TMV) Activity of Phenanthroindolizidines and Their Analogues

  摘要：

  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.

  DOI：

  10.1021/jf303550a