4-羟基-1-甲基-2-氧代-1,2-二氢喹啉-3-羧酸(2-氨基苯基)-胺 | 151449-78-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-羟基-1-甲基-2-氧代-1,2-二氢喹啉-3-羧酸(2-氨基苯基)-胺
• 英文名称: 4-Hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid (2-amino-phenyl)-amide
• 英文别名: N-(2-aminophenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide；N-(2-aminophenyl)-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide
• CAS: 151449-78-4
• 化学式: C₁₇H₁₅N₃O₃
• mdl: MFCD00629253
• 分子量: 309.324
• InChiKey: VHGBPFRMNBEDAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.7
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  4-羟基-1-甲基-2-氧代-1,2-二氢喹啉-3-羧酸(2-氨基苯基)-胺 反应 0.5h， 以95%的产率得到3-(1H-Benzoimidazol-2-yl)-4-hydroxy-1-methyl-1H-quinolin-2-one
  参考文献：
  名称：

  4-Hydroxy-2-quinolones 7. Synthesis and biological properties of 1-R-3-(2-benzimidazolyl)-4-hydroxy-2-quinolones

  摘要：

  DOI：

  10.1007/bf00528643
• 作为产物：
  描述：

  N-甲基蒽 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 4-羟基-1-甲基-2-氧代-1,2-二氢喹啉-3-羧酸(2-氨基苯基)-胺
  参考文献：
  名称：

  Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents

  摘要：

  A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the alpha-lipoic acid functionality were designed and synthesized as potential bifunctional agents combining antioxidant and anti-inflammatory activity. The new compounds were evaluated for their antioxidant activity and for their ability to inhibit in vitro lipoxygenase as well as for their anti-inflammatory activity in vivo. In general, the derivatives were found to be potent antioxidant or anti-inflammatory agents. The results are discussed in terms of structure-activity relationships and an attempt is made to define the structural features required for activity.

  DOI：

  10.1021/jm061173n

文献信息

• Synthesis, X-ray crystallographic study, and biological evaluation of coumarin and quinolinone carboxamides as anticancer agents
  作者：Dimitris Matiadis、Valentina Stefanou、Giorgos Athanasellis、Stylianos Hamilakis、Vickie McKee、Olga Igglessi-Markopoulou、John Markopoulos

  DOI：10.1007/s00706-013-0986-7

  日期：2013.7

  evaluated for its potency in inhibition of cancer cell growth. The structure of N-[2-(dimethylamino) ethyl]-4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinoline-3-carboxamide was unambiguously confirmed by X-ray diffraction analysis, which revealed the cis conformation of the amide bond resulting from the presence of two intramolecular hydrogen bonds. Graphical Abstract

  摘要合成了一系列香豆素和喹啉酮-3-氨基酰胺衍生物，并评估了其抑制癌细胞生长的潜能。的结构ñ - [2-（二甲基氨基）乙基] -4-羟基-2-氧代-1-苯基-1,2-二氢喹啉-3-甲酰胺是明确地通过X射线衍射分析，其显示所确认的顺式构象由两个分子内氢键的存在而产生的酰胺键 图形概要
• Design and Synthesis of Novel Quinolinone-3-aminoamides and Their α-Lipoic Acid Adducts as Antioxidant and Anti-inflammatory Agents
  作者：Anastasia Detsi、Dionysia Bouloumbasi、Kyriakos C. Prousis、Maria Koufaki、Giorgos Athanasellis、Georgia Melagraki、Antreas Afantitis、Olga Igglessi-Markopoulou、Christos Kontogiorgis、Dimitra J. Hadjipavlou-Litina

  DOI：10.1021/jm061173n

  日期：2007.5.1

  A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the alpha-lipoic acid functionality were designed and synthesized as potential bifunctional agents combining antioxidant and anti-inflammatory activity. The new compounds were evaluated for their antioxidant activity and for their ability to inhibit in vitro lipoxygenase as well as for their anti-inflammatory activity in vivo. In general, the derivatives were found to be potent antioxidant or anti-inflammatory agents. The results are discussed in terms of structure-activity relationships and an attempt is made to define the structural features required for activity.
• 4-Hydroxy-2-quinolones 7. Synthesis and biological properties of 1-R-3-(2-benzimidazolyl)-4-hydroxy-2-quinolones
  作者：I. V. Ukrainets、P. A. Bezuglyi、O. V. Gorokhova、V. I. Treskach、A. V. Turov

  DOI：10.1007/bf00528643

  日期：1993.1