1-(2-methyl-4-nitrophenyl)-1H-pyrrole | 383137-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2-methyl-4-nitrophenyl)-1H-pyrrole
• 英文别名: 1H-Pyrrole, 1-(2-methyl-4-nitrophenyl)-；1-(2-methyl-4-nitrophenyl)pyrrole
• CAS: 383137-47-1
• 化学式: C₁₁H₁₀N₂O₂
• mdl: MFCD02665236
• 分子量: 202.213
• InChiKey: CEHOBAIXJWXZRA-UHFFFAOYSA-N

物化性质

• 沸点：
  350.2±35.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-methyl-4-nitrophenyl)-1H-pyrrole 在 乙醇 、 palladium 10% on activated carbon 、 溶剂黄146 作用下， 生成 3-methyl-4-(2-((4-methylpiperazin-1-yl)methyl)-1H-pyrrol-1-yl)aniline
  参考文献：
  名称：

  Structural modifications of indolinones bearing a pyrrole moiety and discovery of a multi-kinase inhibitor with potent antitumor activity

  摘要：

  Structural modifications of compound 2, an angiokinase inhibitor reported by our group were performed, which led to the discovery of methyl (Z)-3-(((4-(2-methyl-5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrol-1-yl)phenyl) amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate (7h). Compound 7h exhibited excellent inhibitory activity against angiokinases including VEGFR-1/2/3, PDGFR alpha/beta, and FGFR-1, as well as LYN and c-KIT kinases. At the cellular level, compound 7h significantly attenuated phosphorylation of AKT and ERK proteins, potently inhibited colony formation of HT-29, MKN74, and HepG2 cancer cells, and induced cell apoptosis. Upon incubation with human liver microsome, 7h exhibited comparable metabolic stability to nintedanib. Compound 7h has emerged as a promising lead compound for future drug design.

  DOI：

  10.1016/j.bmc.2020.115486
• 作为产物：
  描述：

  吡咯 、 2-氟-5-硝基甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以27%的产率得到1-(2-methyl-4-nitrophenyl)-1H-pyrrole
  参考文献：
  名称：

  Structural modifications of indolinones bearing a pyrrole moiety and discovery of a multi-kinase inhibitor with potent antitumor activity

  摘要：

  Structural modifications of compound 2, an angiokinase inhibitor reported by our group were performed, which led to the discovery of methyl (Z)-3-(((4-(2-methyl-5-((4-methylpiperazin-1-yl)methyl)-1H-pyrrol-1-yl)phenyl) amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate (7h). Compound 7h exhibited excellent inhibitory activity against angiokinases including VEGFR-1/2/3, PDGFR alpha/beta, and FGFR-1, as well as LYN and c-KIT kinases. At the cellular level, compound 7h significantly attenuated phosphorylation of AKT and ERK proteins, potently inhibited colony formation of HT-29, MKN74, and HepG2 cancer cells, and induced cell apoptosis. Upon incubation with human liver microsome, 7h exhibited comparable metabolic stability to nintedanib. Compound 7h has emerged as a promising lead compound for future drug design.

  DOI：

  10.1016/j.bmc.2020.115486

文献信息

• Solvent Free Synthesis of N‐Substituted Pyrroles Catalyzed by Calcium Nitrate
  作者：Rucha R. Wani、Hemchandra K. Chaudhari、Balaram S. Takale

  DOI：10.1002/jhet.3507

  日期：2019.4

  Moderated and mild way for synthesizing N‐substituted pyrrole has been demonstrated herein. No solvents need to be used for this reaction, and instead, reactants themselves acted as a reaction medium. In fact, the reaction is carried out using catalytic amount of Ca(NO3)2.4H2O. The reaction conditions are selective and mild that helped to tolerate a wide variety of functional groups to give the desired

  本文已证明了适度温和的合成N-取代吡咯的方法。该反应无需使用溶剂，而是反应物本身充当反应介质。实际上，反应是使用催化量的Ca（NO 3）2 .4H 2 O进行的。反应条件是选择性和温和的，这有助于耐受各种各样的官能团，从而以良好的化学收率得到所需的产物。