(E)-p-nitrophenyl 3-(2-methoxy-5-pyridinyl)acrylate | 221549-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (E)-p-nitrophenyl 3-(2-methoxy-5-pyridinyl)acrylate
• 英文别名: (4-nitrophenyl) (E)-3-(6-methoxypyridin-3-yl)prop-2-enoate
• CAS: 221549-86-6
• 化学式: C₁₅H₁₂N₂O₅
• 分子量: 300.271
• InChiKey: GLSDGYSRHLIGOD-YCRREMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-p-nitrophenyl 3-(2-methoxy-5-pyridinyl)acrylate 在 氢溴酸 、 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 6.17h， 生成 (S)-8-Bromomethyl-4-hydroxy-6-[(E)-3-(6-methoxy-pyridin-3-yl)-acryloyl]-2-methyl-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-1-carboxylic acid methyl ester
  参考文献：
  名称：

  New Water-Soluble Duocarmycin Derivatives: Synthesis and Antitumor Activity of A-Ring Pyrrole Compounds Bearing β-Heteroarylacryloyl Groups

  摘要：

  A series of A-ring pyrrole compounds of duocarmycin bearing 4'-methoxy-beta-heteroarylacryloyl groups were synthesized and evaluated for in vitro anticellular activity against HeLa S-3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. Most of the Li 4'-methoxy-beta-heteroarylacrylates displayed in vitro anticellular activity equivalent to that of 4'-methoxycinnamates, Among the 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxy-beta-heteroarylacrylates, compound 15b having a (4-methoxy-3,5-pyrimidinyl)acryloyl as segment-B (Seg-B) showed remarkably potent in vivo antitumor activity and low peripheral blood toxicity compared with the A-ring pyrrole derivatives having the trimethoxyindole skeleton in Seg-B, which were equal to 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxycinnamates. Moreover, these 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxy-beta-heteroarylacrylates had high aqueous solubility.

  DOI：

  10.1021/jm980559y
• 作为产物：
  描述：

  对硝基苯酚 、 (2E)-3-[6-methoxy(pyridin-3-yl)]prop-2-enoic acid 在 1-methyl-2-chloropyridinium chloride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以72%的产率得到(E)-p-nitrophenyl 3-(2-methoxy-5-pyridinyl)acrylate
  参考文献：
  名称：

  New Water-Soluble Duocarmycin Derivatives: Synthesis and Antitumor Activity of A-Ring Pyrrole Compounds Bearing β-Heteroarylacryloyl Groups

  摘要：

  A series of A-ring pyrrole compounds of duocarmycin bearing 4'-methoxy-beta-heteroarylacryloyl groups were synthesized and evaluated for in vitro anticellular activity against HeLa S-3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. Most of the Li 4'-methoxy-beta-heteroarylacrylates displayed in vitro anticellular activity equivalent to that of 4'-methoxycinnamates, Among the 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxy-beta-heteroarylacrylates, compound 15b having a (4-methoxy-3,5-pyrimidinyl)acryloyl as segment-B (Seg-B) showed remarkably potent in vivo antitumor activity and low peripheral blood toxicity compared with the A-ring pyrrole derivatives having the trimethoxyindole skeleton in Seg-B, which were equal to 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxycinnamates. Moreover, these 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxy-beta-heteroarylacrylates had high aqueous solubility.

  DOI：

  10.1021/jm980559y