4-[4-(Allyloxycarbonylamino-methyl)-phenylamino]-2-phenyl-quinoline-8-carboxylic acid | 651311-50-1

• 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: 4-[4-(Allyloxycarbonylamino-methyl)-phenylamino]-2-phenyl-quinoline-8-carboxylic acid
• 英文别名: 2-phenyl-4-[4-[(prop-2-enoxycarbonylamino)methyl]anilino]quinoline-8-carboxylic acid
• CAS: 651311-50-1
• 化学式: C₂₇H₂₃N₃O₄
• 分子量: 453.497
• InChiKey: RHORJYBQUVYQPD-UHFFFAOYSA-N

物化性质

• 沸点：
  694.7±55.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[4-(Allyloxycarbonylamino-methyl)-phenylamino]-2-phenyl-quinoline-8-carboxylic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 4-[4-[[[(2S)-2-[[(2S)-2-(4-aminobutanoylamino)-3-hydroxypropanoyl]amino]-3-methylbutanoyl]amino]methyl]anilino]-N-[(2S)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-2-phenylquinoline-8-carboxamide
  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：

  8-(methoxycarbonyl)-2-phenyl-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 4.83h， 生成 4-[4-(Allyloxycarbonylamino-methyl)-phenylamino]-2-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+