8-(methoxycarbonyl)-2-(4'-nitrophenyl)-4(1H)-quinolone | 651311-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-(methoxycarbonyl)-2-(4'-nitrophenyl)-4(1H)-quinolone
• 英文别名: methyl 2-(4-nitrophenyl)-4-oxo-1H-quinoline-8-carboxylate
• CAS: 651311-54-5
• 化学式: C₁₇H₁₂N₂O₅
• 分子量: 324.293
• InChiKey: YAGJDJIGWBGDSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  542.6±50.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  102.3
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  8-(methoxycarbonyl)-2-(4'-nitrophenyl)-4(1H)-quinolone 在 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 四氢呋喃 、 氯仿 、 水 、 乙腈 为溶剂， 反应 52.0h， 生成 4-[4-(Allyloxycarbonylamino-methyl)-phenylamino]-2-(4-nitro-phenyl)-quinoline-8-carboxylic acid
  参考文献：
  名称：

  Peptide Quinoline Conjugates:  A New Class of RNA-Binding Molecules

  摘要：

  A synthesis of 4,8-disubstituted 2-phenylquinoline amino acids is reported with the incorporation of one example into a peptide by solid-phase synthesis. The phenylquinoline-containing peptide binds an RNA target with nanomolar affinity (K-D = 208 nM). The strategy can be used to prepare a variety of 2-substituted quinoline amino acids for alteration of affinity in intercalator peptides. Since quinolones represent an important class of antibacterials, these compounds may be useful in the discovery of new antibacterial agents.

  DOI：

  10.1021/ol036094+
• 作为产物：
  描述：

  对硝基苯甲酰醋酸乙酯 、 邻氨基苯甲酸甲酯 在 甲烷磺酸 作用下， 以 苯 、 二苯醚 为溶剂， 反应 44.25h， 以28%的产率得到8-(methoxycarbonyl)-2-(4'-nitrophenyl)-4(1H)-quinolone
  参考文献：
  名称：

  Peptide Quinoline Conjugates:  A New Class of RNA-Binding Molecules

  摘要：

  A synthesis of 4,8-disubstituted 2-phenylquinoline amino acids is reported with the incorporation of one example into a peptide by solid-phase synthesis. The phenylquinoline-containing peptide binds an RNA target with nanomolar affinity (K-D = 208 nM). The strategy can be used to prepare a variety of 2-substituted quinoline amino acids for alteration of affinity in intercalator peptides. Since quinolones represent an important class of antibacterials, these compounds may be useful in the discovery of new antibacterial agents.

  DOI：

  10.1021/ol036094+

文献信息

• Peptide Quinoline Conjugates:  A New Class of RNA-Binding Molecules
  作者：Malathy Krishnamurthy、Barry D. Gooch、Peter A. Beal

  DOI：10.1021/ol036094+

  日期：2004.1.1

  A synthesis of 4,8-disubstituted 2-phenylquinoline amino acids is reported with the incorporation of one example into a peptide by solid-phase synthesis. The phenylquinoline-containing peptide binds an RNA target with nanomolar affinity (K-D = 208 nM). The strategy can be used to prepare a variety of 2-substituted quinoline amino acids for alteration of affinity in intercalator peptides. Since quinolones represent an important class of antibacterials, these compounds may be useful in the discovery of new antibacterial agents.