6-oxo-6H-imidazo(4,5,1-ij)quinoline-4-carboxylic acid methyl ester | 94110-84-6

• 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: 6-oxo-6H-imidazo(4,5,1-ij)quinoline-4-carboxylic acid methyl ester
• 英文别名: Methyl 9-oxo-1,3-diazatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12),10-pentaene-11-carboxylate
• CAS: 94110-84-6
• 化学式: C₁₂H₈N₂O₃
• 分子量: 228.207
• InChiKey: OGPFLYVIYYKOEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-oxo-6H-imidazo(4,5,1-ij)quinoline-4-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 反应 0.25h， 以86%的产率得到8-(formylamino)-1,4-dihydro-4-oxo-2-quinolinecarboxylic acid
  参考文献：
  名称：

  Synthesis and antiallergic activity of some quinolinones and imidazoquinolinones

  摘要：

  A group of 1,4-dihydro-4-oxoquinoline-2- and -3-carboxylic acid esters with nitrogen functionality at the 8-position was synthesized, and 6-oxo-6H-imidazo[4,5,1-ij]quinoline-4- and -5-carboxylic acid esters were elaborated from these. Several of the compounds displayed activity in the rat passive cutaneous anaphylaxis (PCA) test for antiallergic activity. However, PCA activity in this series was accompanied by rat toxicity, as measured by a decrease in percent of normal weight gain over a 2-week period, following a single oral dose.

  DOI：

  10.1021/jm00381a007
• 作为产物：
  描述：

  8-硝基-4-氧代-1,4-二氢喹啉-2-羧酸甲酯 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.5h， 生成 6-oxo-6H-imidazo(4,5,1-ij)quinoline-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and antiallergic activity of some quinolinones and imidazoquinolinones

  摘要：

  A group of 1,4-dihydro-4-oxoquinoline-2- and -3-carboxylic acid esters with nitrogen functionality at the 8-position was synthesized, and 6-oxo-6H-imidazo[4,5,1-ij]quinoline-4- and -5-carboxylic acid esters were elaborated from these. Several of the compounds displayed activity in the rat passive cutaneous anaphylaxis (PCA) test for antiallergic activity. However, PCA activity in this series was accompanied by rat toxicity, as measured by a decrease in percent of normal weight gain over a 2-week period, following a single oral dose.

  DOI：

  10.1021/jm00381a007

文献信息

• PEET, N. P.;BAUGH, L. E.;SUNDER, SHYAM;LEWIS, J. E., J. MED. CHEM., 1985, 28, N 3, 298-302
  作者：PEET, N. P.、BAUGH, L. E.、SUNDER, SHYAM、LEWIS, J. E.

  DOI：——

  日期：——