(3-amino-1H-indol-2-yl)-naphthalen-1-yl-methanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3-amino-1H-indol-2-yl)-naphthalen-1-yl-methanone
• 英文别名: (3-amino-1H-indol-2-yl)-naphthalen-1-ylmethanone
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: PAYXYYRKNPGZKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2-氰基苯基)氨基甲酸乙酯 、 2-溴-1-萘-1-乙酮 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以93%的产率得到(3-amino-1H-indol-2-yl)-naphthalen-1-yl-methanone
  参考文献：
  名称：

  3-氨基-1H-吲哚和3-氨基-1H-7-氮杂吲哚的简便的一锅合成，抗增殖评价和构效关系。

  摘要：

  从2-氰基苯基氨基甲酸乙酯/ 3-氰基吡啶-2-乙基氨基甲酸乙酯开始，已经开发了一种高效方法，用于一锅合成取代的3-氨基-1H-吲哚和3-氨基-1H-7-氮杂吲哚衍生物。 α-溴酮的收率为好至极好。筛选所有新合成的类似物对四种癌细胞系的抗增殖活性。与氟尿嘧啶相比，最有希望的化合物8v在抑制HeLa，HepG2和MCF-7细胞增殖方面表现出13倍，5倍和1.4倍的改善，IC50值分别为3.7、8.0和19.9μM。此外，8v通过浓度依赖性的方式在HeLa细胞系的G2 / M期诱导了明显的细胞周期停滞。

  DOI：

  10.1016/j.bioorg.2019.04.008

文献信息

• TEST KIT FOR THE QUANTITATIVE DETERMINATION OF NARCOTIC DRUGS
  申请人：CHIRON AS

  公开号：US20150204893A1

  公开（公告）日：2015-07-23

  A test kit for the quantitative determination of narcotic drugs comprising (A) series of sealed vessels, each vessel containing a deuterium free isotopologue of a narcotic drug in exactly defined concentrations and quantities, wherein the isotopologue differs from vessel to vessel and—wherein the quantities of the isotopologue differ from vessel to vessel or are the same for all vessels; and/or (B) series of sealed vessels, each vessel containing in exactly defined concentrations and quantities the same isotopologue in quantities which differ from vessel to vessel; wherein the free isotopologues are selected from narcotic drugs; prodrugs, salts, solvates, hydrates and polymorphs and contain at least three stable isotopes selected from the group consisting of 13 C, 15 N and 18 O in the molecule with a degree of labeling of at least 95 mol-%; the use of the test kit and a method for quantitatively determining narcotic drugs.

  一种用于定量测定麻醉药物的检测试剂盒，包括（A）一系列密封容器，每个容器中含有一种去氘同位素麻醉药物，其浓度和数量均被精确定义，其中同位素从容器到容器不同，同位素的数量在容器到容器之间不同或对所有容器都相同；和/或（B）一系列密封容器，每个容器中含有相同的同位素，其浓度和数量被精确定义，数量在容器到容器之间不同；其中自由同位素选自麻醉药物、前药、盐、溶剂、水合物和多晶形，并且在分子中至少包含三种稳定同位素，所述稳定同位素选自13C、15N和18O，其标记度至少为95摩尔％；使用该检测试剂盒和一种定量测定麻醉药物的方法。
• Test kit for the quantitative determination of narcotic drugs
  申请人：Chiron AS

  公开号：EP2687854A1

  公开（公告）日：2014-01-22

  A test kit for the quantitative determination of narcotic drugs comprising (A) series of sealed vessels, each vessel containing a deuterium free isotopologue of a narcotic drug in exactly defined concentrations and quantities, - wherein the isotopologue differs from vessel to vessel and - wherein the quantities of the isotopologue differ from vessel to vessel or are the same for all vessels; and/or (B) series of sealed vessels, each vessel containing in exactly defined concentrations and quantities the same isotopologue in quantities which differ from vessel to vessel; - wherein the free isotopologues are selected from narcotic drugs; prodrugs, salts, solvates, hydrates and polymorphs and contain at least three stable isotopes selected from the group consisting of 13C, 15N and 18O in the molecule with a degree of labeling of at least 95 mol-%; the use of the test kit and a method for quantitatively determining narcotic drugs.

  用于定量测定麻醉药品的试剂盒，包括 (A) 一系列密封容器，每个容器装有浓度和数量完全确定的麻醉药品的无 氘同位素、 - 其中各容器的同位素不同，并且 - 其中同位素的数量因容器而异或所有容器相同；和/或 (B) 一系列密封容器，每个容器以完全确定的浓度和数量含有相同的同位 素，其数量因容器而异； - 其中游离的同位素选自麻醉药品；原药、盐、溶液、水合物和多晶型物，以及 分子中至少含有三个稳定同位素，选自 13C、15N 和 18O 组成的组，标记度至少为 95 摩尔-%； 使用检测试剂盒和方法定量测定麻醉药品。
• US9347961B2
  申请人：——

  公开号：US9347961B2

  公开（公告）日：2016-05-24
• [EN] TEST KIT FOR THE QUANTITATIVE DETERMINATION OF NARCOTIC DRUGS<br/>[FR] KIT DE TEST POUR LA DÉTERMINATION QUANTITATIVE DE STUPÉFIANTS
  申请人：CHIRON AS

  公开号：WO2014013063A1

  公开（公告）日：2014-01-23

  A test kit for the quantitative determination of narcotic drugs comprising (A) series of sealed vessels, each vessel containing a deuterium free isotopologue of a narcotic drug in exactly defined concentrations and quantities, wherein the isotopologue differs from vessel to vessel and - wherein the quantities of the isotopologue differ from vessel to vessel or are the same for all vessels; and/or (B) series of sealed vessels, each vessel containing in exactly defined concentrations and quantities the same isotopologue in quantities which differ from vessel to vessel; wherein the free isotopologues are selected from narcotic drugs; prodrugs, salts, solvates, hydrates and polymorphs and contain at least three stable isotopes selected from the group consisting of 13C, 15N and 180 in the molecule with a degree of labeling of at least 95 mol-%; the use of the test kit and a method for quantitatively determining narcotic drugs.
• Facile one-pot synthesis, antiproliferative evaluation and structure-activity relationships of 3-amino-1H-indoles and 3-amino-1H-7-azaindoles
  作者：Peng-Cheng Diao、Meng-Jin Hu、Hai-Kui Yang、Wen-Wei You、Pei-Liang Zhao

  DOI：10.1016/j.bioorg.2019.04.008

  日期：2019.7

  A highly efficient method has been developed for the one-pot synthesis of substituted 3-amino-1H-indole and 3-amino-1H-7-azaindole derivatives starting from ethyl 2-cyanophenylcarbamate/ethyl 3-cyanopyridin-2-ylcarbamate, and α-bromoketones in good to excellent yields. All newly synthesized analogues were screened for their antiproliferative activities against four cancer cell lines. The most promising

  从2-氰基苯基氨基甲酸乙酯/ 3-氰基吡啶-2-乙基氨基甲酸乙酯开始，已经开发了一种高效方法，用于一锅合成取代的3-氨基-1H-吲哚和3-氨基-1H-7-氮杂吲哚衍生物。 α-溴酮的收率为好至极好。筛选所有新合成的类似物对四种癌细胞系的抗增殖活性。与氟尿嘧啶相比，最有希望的化合物8v在抑制HeLa，HepG2和MCF-7细胞增殖方面表现出13倍，5倍和1.4倍的改善，IC50值分别为3.7、8.0和19.9μM。此外，8v通过浓度依赖性的方式在HeLa细胞系的G2 / M期诱导了明显的细胞周期停滞。