(2,3,6-Trifluorophenyl) 1,6-dimethoxy-4-methylacridine-9-carboxylate | 197156-27-7

• 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: (2,3,6-Trifluorophenyl) 1,6-dimethoxy-4-methylacridine-9-carboxylate
• CAS: 197156-27-7
• 化学式: C₂₃H₁₆F₃NO₄
• 分子量: 427.38
• InChiKey: GQQFRGFKGFOBCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2,3,6-Trifluorophenyl) 1,6-dimethoxy-4-methylacridine-9-carboxylate 在 氯化铵 、 锌 作用下， 以 异丙醇 为溶剂， 反应 2.5h， 以29.5 mg的产率得到(2,3,6-trifluorophenyl) 1,6-dimethoxy-4-methyl-9,10-dihydroacridine-9-carboxylate
  参考文献：
  名称：

  Characterization of Acridancarboxylic Acid Derivatives as Chemiluminescent Peroxidase Substrates

  摘要：

  A new class of peroxidase substrates has been developed which produces chemiluminescence upon enzymatic oxidation. A wide variety of N-alkylacridancarboxylic acid derivatives including esters, thioesters, and sulfonamides are efficiently oxidized by a peroxidase and a peroxide to enzymatically produce the corresponding chemiluminescent acridinium compound, In conjunction with a peroxidase enhancer, continuous light emission with high light intensities and an extended duration are produced, Alternately, an appropriately designed acridan substrate produces a stable acridinium ester intermediate which can be accumulated and the chemiluminescence elicited as a burst of light by raising the pH. The effects of leaving groups and substitution on the acridan ring on the mechanism of light production are discussed, Peroxidase-catalyzed oxidation in the presence of a peroxide permits the detection of enzyme with subattomolar sensitivity and a broad linear dynamic range.

  DOI：

  10.1021/jo970202m
• 作为产物：
  描述：

  5-甲氧基-2-甲基苯胺 在 吡啶 、 氢氧化钾 、 copper(l) iodide 、 三氯化铝 、 potassium carbonate 、 对甲苯磺酰氯 、 锌 作用下， 以 溶剂黄146 为溶剂， 反应 51.42h， 生成 (2,3,6-Trifluorophenyl) 1,6-dimethoxy-4-methylacridine-9-carboxylate
  参考文献：
  名称：

  Characterization of Acridancarboxylic Acid Derivatives as Chemiluminescent Peroxidase Substrates

  摘要：

  A new class of peroxidase substrates has been developed which produces chemiluminescence upon enzymatic oxidation. A wide variety of N-alkylacridancarboxylic acid derivatives including esters, thioesters, and sulfonamides are efficiently oxidized by a peroxidase and a peroxide to enzymatically produce the corresponding chemiluminescent acridinium compound, In conjunction with a peroxidase enhancer, continuous light emission with high light intensities and an extended duration are produced, Alternately, an appropriately designed acridan substrate produces a stable acridinium ester intermediate which can be accumulated and the chemiluminescence elicited as a burst of light by raising the pH. The effects of leaving groups and substitution on the acridan ring on the mechanism of light production are discussed, Peroxidase-catalyzed oxidation in the presence of a peroxide permits the detection of enzyme with subattomolar sensitivity and a broad linear dynamic range.

  DOI：

  10.1021/jo970202m

文献信息

• Characterization of Acridancarboxylic Acid Derivatives as Chemiluminescent Peroxidase Substrates
  作者：Hashem Akhavan-Tafti、Renuka DeSilva、Zahra Arghavani、Robert A. Eickholt、Richard S. Handley、Barry A. Schoenfelner、Katsuaki Sugioka、Yumiko Sugioka、A. Paul Schaap

  DOI：10.1021/jo970202m

  日期：1998.2.1

  A new class of peroxidase substrates has been developed which produces chemiluminescence upon enzymatic oxidation. A wide variety of N-alkylacridancarboxylic acid derivatives including esters, thioesters, and sulfonamides are efficiently oxidized by a peroxidase and a peroxide to enzymatically produce the corresponding chemiluminescent acridinium compound, In conjunction with a peroxidase enhancer, continuous light emission with high light intensities and an extended duration are produced, Alternately, an appropriately designed acridan substrate produces a stable acridinium ester intermediate which can be accumulated and the chemiluminescence elicited as a burst of light by raising the pH. The effects of leaving groups and substitution on the acridan ring on the mechanism of light production are discussed, Peroxidase-catalyzed oxidation in the presence of a peroxide permits the detection of enzyme with subattomolar sensitivity and a broad linear dynamic range.