3-methoxyacridine-9-carboxylic acid | 172834-71-8

• 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: 3-methoxyacridine-9-carboxylic acid
• 英文别名: 3-Methoxy-acridine-9-carboxylic acid
• CAS: 172834-71-8
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: OUPQDYSDWSHINB-UHFFFAOYSA-N

物化性质

• 沸点：
  508.9±20.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxyacridine-9-carboxylic acid 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2,3,6-Trifluorophenyl) 3-methoxyacridine-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：

  草酰氯 、 3-甲氧基二苯胺 在 三氯化铝 作用下， 生成 3-methoxyacridine-9-carboxylic acid
  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

• Compounds, compositions and methods for generating chemiluminescence with phosphatase enzymes
  申请人：——

  公开号：US20030023089A1

  公开（公告）日：2003-01-30

  Novel heterocyclic compounds which generate chemiluminescence on reaction with a phosphatase enzyme are provided as well as a process for their preparation and intermediates useful therein. The compounds comprise a nitrogen, oxygen or sulfur-containing heterocyclic ring system bearing an exocyclic carbon-carbon double bond. The double bond is further substituted at the distal carbon with a phosphate group and an oxygen or sulfur atom-containing group. Novel compositions further comprising a cationic aromatic compound (CAC) in addition to the heterocyclic phosphate compound are provided. The addition of the CAC in the composition greatly increases the production of chemiluminescence and provides improved detection sensitivity. Compositions further comprising an anionic surfactant and a non-ionic surfactant provide additional improvements in detection sensitivity. The novel chemiluminescent compounds and compositions are useful in methods for producing light and in assays for phosphatase enzymes and enzyme inhibitors and in assays employing enzyme-labeled specific binding pairs.

  本发明提供了产生化学发光的新型杂环化合物，其与磷酸酶酶反应时会产生化学发光，以及用于其制备和有用中间体的方法。该化合物包括带有外向碳-碳双键的氮、氧或硫含杂环环系统。双键在远端碳上进一步取代为一个磷酸酯基团和一个含氧或硫原子的基团。此外，本发明还提供了进一步包括阳离子芳香化合物（CAC）的新型组合物，除了杂环磷酸酯化合物外。在组合物中加入CAC可以大大增加化学发光的产生，并提供改进的检测灵敏度。进一步包括阴离子表面活性剂和非离子表面活性剂的组合物提供了额外的检测灵敏度改进。新型化学发光化合物和组合物在产生光的方法、磷酸酶酶和酶抑制剂的检测方法以及使用酶标记的特异性结合对的检测方法中均有用途。
• Compounds, compositions and methods for generating chemiluminescence
  申请人：Lumigen, Inc.

  公开号：US06090571A1

  公开（公告）日：2000-07-18

  Novel heterocyclic compounds which generate chemiluminescence on reaction with a phosphatase enzyme are provided as well as a process for their preparation and intermediates useful therein. The compounds comprise a nitrogen, oxygen or sulfur-containing heterocyclic ring system bearing an exocyclic carbon-carbon double bond. The double bond is further substituted at the distal carbon with a phosphate group and an oxygen or sulfur atom-containing group. Novel compositions further comprising a cationic aromatic compound (CAC) in addition to the heterocyclic phosphate compound are provided. The addition of the CAC in the composition greatly increases the production of chemiluminescence and provides improved detection sensitivity. Compositions further comprising an anionic surfactant and a non-ionic surfactant provide additional improvements in detection sensitivity. The novel chemiluminescent compounds and compositions are useful in methods for producing light and in assays for phosphatase enzymes and enzyme inhibitors and in assays employing enzyme-labeled specific binding pairs.

  本发明提供了一种产生化学发光的新型杂环化合物，其与磷酸酶酶反应时会产生化学发光，并提供了其制备方法和有用中间体。该化合物包括一个含氮、氧或硫的杂环环系，其带有一个外环碳-碳双键。该双键在远端碳上进一步取代了一个磷酸酯基团和一个含氧或硫的原子基团。此外，还提供了一种新型组合物，其中除了杂环磷酸酯化合物外，还包括一个阳离子芳香化合物（CAC）。在组合物中加入CAC可以极大地增加化学发光的产生，并提高检测灵敏度。进一步包括阴离子表面活性剂和非离子表面活性剂的组合物提供了额外的检测灵敏度改进。新型化学发光化合物和组合物可用于产生光的方法，以及用于磷酸酶酶和酶抑制剂的测定和使用酶标记的特异性结合对的测定。
• High Quantum Yield Acridinium Compounds and Their Uses in Improving Assay Sensitivity
  申请人：Natrajan Anand

  公开号：US20080014660A1

  公开（公告）日：2008-01-17

  The present invention relates to hydrophilic, high quantum yield acridinium compounds. It has been discovered that the placement of electron-donating groups in the acridinium ring system increases the amount of light that is emitted by the corresponding acridinium compound when its chemiluminescence is triggered by alkaline peroxide. More specifically, it has been found that the placement of one or two hydrophilic, alkoxy groups at the C-2 and/or C-7 position of the acridinium ring system of acridinium compounds increases their quantum yield and enhances the aqueous solubility of these compounds. The present hydrophilic, high quantum yield, acridinium compounds are useful chemiluminescent labels for improving the sensitivity of immunoassays.

  本发明涉及亲水性高量子产率的吖啶类化合物。已经发现，在吖啶环系中引入电子供体基团可以增加相应吖啶化合物在碱性过氧化物引发的化学发光时所发射的光量。更具体地，发现在吖啶环系的C-2和/或C-7位置引入一个或两个亲水性的烷氧基团可以增加吖啶类化合物的量子产率并提高这些化合物的水溶性。本发明的亲水性高量子产率的吖啶类化合物是用于提高免疫分析灵敏度的有用化学发光标记。
• [EN] CHEMILUMINESCENT DETECTION OF HYDROLYTIC ENZYMES USING AN ACRIDAN<br/>[FR] DETECTION PAR CHIMIOLUMINESCENCE D'ENZYMES HYDROLYTIQUES A L'AIDE D'UN ACRIDAN
  申请人：LUMIGEN, INC.

  公开号：WO1996007911A1

  公开（公告）日：1996-03-14

  (EN) A chemiluminescent assay method, compositions and kits are described which use a protected phenolic enhancer compound which is deprotected by a hydrolytic enzyme and then enhances a chemiluminescent reaction. The reaction involves an acridan compound, preferably a derivative of an N-alkyl-acridan-9-carboxylic acid, which is activated to produce light by a peroxide compound and a peroxidase enzyme in the presence of the deprotected enhancer. The result is enhanced generation of light from the reaction. The hydrolytic enzyme is present alone or linked to a member of a specific binding pair in an immunoassay, DNA probe assay or other assay where the hydrolytic enzyme is bound to a reporter molecule.(FR) Procédé de détection par chimioluminescence et compositions et trousses associées, dans lesquels on utilise un composé activateur phénolique protégé, qui, lorsqu'il est déprotégé par une enzyme hydrolytique, amplifie une réaction. La réaction fait appel à un composé d'acridan, de préférence à un dérivé d'un acide N-alkyl-acridan-9-carboxylique, qui est activé pour produire de la lumière par un composé de peroxyde et par une enzyme de type peroxydase en présence de l'activateur déprotégé. Il résulte de la réaction une production accrue de lumière. L'enzyme hydrolytique est présente seule ou liée à l'un des éléments d'une paire de liaison spécifique dans un dosage immunologique, dans un dosage par sonde d'ADN ou dans d'autres types de dosages où l'enzyme hydrolytique se trouve liée à une molécule reporteur.

  一种化学发光反应方法及组件和试剂盒，所述方法使用一种受保护的酚酸增强剂，该增强剂经水解酶解后可以增强化学发光反应。所述反应包括一种酸酐酸，优先为N-甲基丙烯酸-9-酸的衍生物，该酸酐酸在过氧化物和过氧化酶的作用下，在解除了增强剂的保护后的条件下发光。该反应来源的发光量得到了增强。水解酶Present alone or linked to a specific binding pair member in an immunoassay, DNA probe assay or other assay in which the hydrolytic enzyme is bound to a reporter molecule. 化学发光检测方法及试剂盒，其中包括一种受保护的酚酸增强剂，该增强剂经水解后可以增强电化学反应。反应包括酸酐酸，最好是N-甲基丙烯酸-9-酸的衍生物，能够经由过氧化物和过氧化酶在解除了增强剂的保护后的条件下发出光。该反应的出现可以呈现颜色变化或光信号。所述水解酶独立存在或者被连接到一种特定配对 member在酶标片、DNA探针检测或者其它酶标或采用带报告分子的酶标方法中的检测试剂盒。
• NOVEL ARYL N-ALKYLACRIDANCARBOXYLATE DERIVATIVES USEFUL FOR CHEMILUMINESCENT DETECTION
  申请人：LUMIGEN, INC.

  公开号：EP0750748A1

  公开（公告）日：1997-01-02