2-Methyl-4-(p-nitrophenyl)-pyrrol-3-carbonsaeureethylester | 5881-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-Methyl-4-(p-nitrophenyl)-pyrrol-3-carbonsaeureethylester
• 英文别名: 2-methyl-4-(4-nitro-phenyl)-pyrrole-3-carboxylic acid ethyl ester；ethyl 2-methyl-4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate
• CAS: 5881-57-2
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: WPOPTEQBHPYPBL-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  494.9±45.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methyl-4-(p-nitrophenyl)-pyrrol-3-carbonsaeureethylester 在 三氟乙酸 作用下， 以600 mg的产率得到2-Methyl-4-(4-nitro-phenyl)-1H-pyrrole
  参考文献：
  名称：

  Virtual screening and further development of novel ALK inhibitors

  摘要：

  Anaplastic lymphoma kinase (ALK) has been in the spotlight in recent years as a promising new target for therapy of non-small-cell lung cancer (NSCLC). Since the identification of the echinoderm microtubule-associated protein-like 4 (EML4)-ALK fusion gene in some NSCLC patients was reported in 2007, various research groups have been seeking ALK inhibitors. Above all, crizotinib (PF-02341066) has been under clinical trial, and its therapeutic efficacy of inhibiting ALK in NSCLC has been reported. Among anticancer drugs, drug resistance appears frequently necessitating various kinds of inhibitors. We identified novel ALK inhibitors by virtual screening from the public chemical library collected by the Chemical Biology Research Initiative (CBRI) at the University of Tokyo, and inhibitors that are more potent were developed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.008
• 作为产物：
  描述：

  1-硝基,2-(4-硝基苯基)-乙烯 、 乙酰乙酸乙酯 在 sodium methylate 、 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以4.2 g的产率得到2-Methyl-4-(p-nitrophenyl)-pyrrol-3-carbonsaeureethylester
  参考文献：
  名称：

  Virtual screening and further development of novel ALK inhibitors

  摘要：

  Anaplastic lymphoma kinase (ALK) has been in the spotlight in recent years as a promising new target for therapy of non-small-cell lung cancer (NSCLC). Since the identification of the echinoderm microtubule-associated protein-like 4 (EML4)-ALK fusion gene in some NSCLC patients was reported in 2007, various research groups have been seeking ALK inhibitors. Above all, crizotinib (PF-02341066) has been under clinical trial, and its therapeutic efficacy of inhibiting ALK in NSCLC has been reported. Among anticancer drugs, drug resistance appears frequently necessitating various kinds of inhibitors. We identified novel ALK inhibitors by virtual screening from the public chemical library collected by the Chemical Biology Research Initiative (CBRI) at the University of Tokyo, and inhibitors that are more potent were developed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.008

文献信息

• REGIOSELECTIVITY OF THE METHYL-TOSMIC REACTION WITH SUBSTITUTED ETHYL CINNAMATES
  作者：Roberto Di Santo、Roberta Costi、Carlo Galeffi、Michela Forte

  DOI：10.1080/00304940509354884

  日期：2005.4

  with the above mentioned olefin derivative^.'.^-^ Our decade-long interest in the chemistry of pyrrole annulated heterocyclic systems led us to explore new routes to synthesize 2H-pyrrolo[3,4-c]quinoline derivatives, with the aim to obtain new potential ligands of the 5-HT receptors. A recent papers reported the synthesis of 1 substituted 2H-pyrrolo[3,4-c]quinolines via the Me-TosMIC reaction with ethyl

  甲苯磺酰甲基异氰化物 (TosMIC) 是一种有吸引力的结构单元，可用于合成环酮、腈、胺，尤其是杂环合成。具有与吸电子基团共轭的碳碳双键的物质，如羰基、腈和硝基，已广泛用于使用金属化甲苯磺酰甲基异氰化物合成 3,4-二取代吡咯。1-4 此外，通过 a-单取代的 TosMIC 与上述烯烃衍生物反应获得 2,3,4-三取代的吡咯^.'.^-^ 我们对吡咯环状杂环系统化学的长达十年的兴趣使我们探索合成2H-吡咯并[3,4-c]喹啉衍生物的新途径，以期获得5-HT受体新的潜在配体。最近的一篇论文报道了通过 Me-TosMIC 与肉桂酸乙酯的反应合成 1 取代的 2H-吡咯并 [3,4-c] 喹啉。令人惊讶的是，2-硝基肉桂酸乙酯与 Me-TosMIC 的反应旨在获得关键中间体 2-甲基-3-(2-硝基苯基)1H-吡咯-4-羧酸乙酯 (2a)，得到预期的 2a 和其异构体 2-甲基-4-(2-硝基苯