(R)-1-[(9-bromo-2,3,6,7-tetramethoxyphenanthren-10-yl)methyl]pyrrolidine-2-carboxamide | 1394286-36-2

• 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: (R)-1-[(9-bromo-2,3,6,7-tetramethoxyphenanthren-10-yl)methyl]pyrrolidine-2-carboxamide
• 英文别名: (2R)-1-[(10-bromo-2,3,6,7-tetramethoxyphenanthren-9-yl)methyl]pyrrolidine-2-carboxamide
• CAS: 1394286-36-2
• 化学式: C₂₄H₂₇BrN₂O₅
• 分子量: 503.393
• InChiKey: IZUTWKFKUGEKHR-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  83.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-1-[(9-bromo-2,3,6,7-tetramethoxyphenanthren-10-yl)methyl]pyrrolidine-2-carboxamide 在 copper(l) iodide 、 N,N-二甲基甘氨酸盐酸盐 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以84%的产率得到(R)-2,3,6,7-tetramethoxy-10a,11,12,13-tetrahydro-9H-phenanthro[9,10-e]pyrrolo[1,2-a][1,4]diazepin-10(15H)-one
  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 、 D-脯氨酰胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以91%的产率得到(R)-1-[(9-bromo-2,3,6,7-tetramethoxyphenanthren-10-yl)methyl]pyrrolidine-2-carboxamide
  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