(7-hydroxy-2-oxo-2H-chromen-4-yl)methanaminium chloride | 72304-29-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (7-hydroxy-2-oxo-2H-chromen-4-yl)methanaminium chloride
• 英文别名: 4-(Aminomethyl)-7-hydroxychromen-2-one;hydrochloride；4-(aminomethyl)-7-hydroxychromen-2-one;hydrochloride
• CAS: 72304-29-1
• 化学式: C₁₀H₉NO₃*ClH
• 分子量: 227.647
• InChiKey: QYBJXPSNMHAOLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (7-hydroxy-2-oxo-2H-chromen-4-yl)methanaminium chloride 在 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (7-((butoxycarbonyl)oxy)-2-oxo-2H-chromen-4-yl)methanaminium 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Development of a Fluorogenic Probe with a Transesterification Switch for Detection of Histone Deacetylase Activity

  摘要：

  Histone deacetylases (HDACs) are key enzymatic regulators of many cellular processes such as gene expression, cell cycle, and tumorigenesis. These enzymes are attractive targets for drug development. However, very few simple methods for monitoring HDAC activity have been reported. Here, we have developed a fluorogenic probe, K4(Ac)-CCB, which consists of the histone H3 peptide containing acetyl-Lys and a coumarin fluorophore with a carbonate ester. By the simple addition of the probe to a HDAC solution, enzyme activity was clearly detected through spontaneous intramolecular transesterification, which renders the probe fluorescent. In addition, K4(Ac)-CCB can be applied to the evaluation of HDAC inhibitor activity. This is the first report to demonstrate the monitoring of HDAC activity by using a one-step procedure. Thus, our novel fluorogenic probe will provide a powerful tool for epigenetic research and the discovery of HDAC-targeted drugs.

  DOI：

  10.1021/ja306045j
• 作为产物：
  描述：

  间苯二酚 在 ammonium hydroxide 、 硫酸 作用下， 以 水 为溶剂， 反应 14.0h， 生成 (7-hydroxy-2-oxo-2H-chromen-4-yl)methanaminium chloride
  参考文献：
  名称：

  Development of a Fluorogenic Probe with a Transesterification Switch for Detection of Histone Deacetylase Activity

  摘要：

  Histone deacetylases (HDACs) are key enzymatic regulators of many cellular processes such as gene expression, cell cycle, and tumorigenesis. These enzymes are attractive targets for drug development. However, very few simple methods for monitoring HDAC activity have been reported. Here, we have developed a fluorogenic probe, K4(Ac)-CCB, which consists of the histone H3 peptide containing acetyl-Lys and a coumarin fluorophore with a carbonate ester. By the simple addition of the probe to a HDAC solution, enzyme activity was clearly detected through spontaneous intramolecular transesterification, which renders the probe fluorescent. In addition, K4(Ac)-CCB can be applied to the evaluation of HDAC inhibitor activity. This is the first report to demonstrate the monitoring of HDAC activity by using a one-step procedure. Thus, our novel fluorogenic probe will provide a powerful tool for epigenetic research and the discovery of HDAC-targeted drugs.

  DOI：

  10.1021/ja306045j

文献信息

• NOVEL COUMARIN DERIVATIVE
  申请人：Nagano Tetsuo

  公开号：US20070197778A1

  公开（公告）日：2007-08-23

  A compound represented by the following general formula (I) or a salt thereof [R 1 represents hydrogen atom, or a C 1-12 alkyl group; R 2 represents a C 1-12 alkyl group having one or more maleimide groups, an aryl group having two or more maleimide groups, a group represented by the formula (A): —(CH 2 ) n —CO—N(R 11 )(R 12 ) (R 11 and R 12 represent hydrogen atom, a C 1-12 alkyl group, a C 1-12 alkyl group having one or more maleimide groups, or an aryl group having one or more maleimide groups, and n represents an integer of 1 to 6), or a group represented by the formula (B): —(CH 2 ) m —NH—CO—R 13 (R 13 represents a C 1-12 alkyl group having one or more maleimide groups, or an aryl group having one or more maleimide groups, and m represents an integer of 1 to 6); R 3 and R 5 represent hydrogen atom, or a halogen atom; R 4 represents hydroxyl group, a C 1-12 acyloxy group, a C 1-12 acyloxymethyloxy group, or an amino group], which is useful as a novel fluorescent labeling agent having a property of emitting intense fluorescence only after reacting with a thiol group.
• NOVEL COUMARIN DERIVATIVES
  申请人：NAGANO Tetsuo

  公开号：US20090118471A1

  公开（公告）日：2009-05-07

  A compound represented by the following general formula (I) or a salt thereof [R 1 represents hydrogen atom, or a C 1-12 alkyl group; R 2 represents a C 1-12 alkyl group having one or more maleimide groups, an aryl group having two or more maleimide groups, a group represented by the formula (A): —(CH 2 ) n —CO—N(R 11 )(R 12 ) (R 11 and R 12 represent hydrogen atom, a C 1-12 alkyl group, a C 1-12 alkyl group having one or more maleimide groups, or an aryl group having one or more maleimide groups, and n represents an integer of 1 to 6), or a group represented by the formula (B): —(CH 2 ) m —NH—CO—R 13 (R 13 represents a C 1-12 alkyl group having one or more maleimide groups, or an aryl group having one or more maleimide groups, and m represents an integer of 1 to 6); R 3 and R 5 represent hydrogen atom, or a halogen atom; R 4 represents hydroxyl group, a C 1-12 acyloxy group, a C 1-12 acyloxymethyloxy group, or an amino group], which is useful as a novel fluorescent labeling agent having a property of emitting intense fluorescence only after reacting with a thiol group.
• US7482473B2
  申请人：——

  公开号：US7482473B2

  公开（公告）日：2009-01-27
• Development of a Fluorogenic Probe with a Transesterification Switch for Detection of Histone Deacetylase Activity
  作者：Reisuke Baba、Yuichiro Hori、Shin Mizukami、Kazuya Kikuchi

  DOI：10.1021/ja306045j

  日期：2012.9.5

  Histone deacetylases (HDACs) are key enzymatic regulators of many cellular processes such as gene expression, cell cycle, and tumorigenesis. These enzymes are attractive targets for drug development. However, very few simple methods for monitoring HDAC activity have been reported. Here, we have developed a fluorogenic probe, K4(Ac)-CCB, which consists of the histone H3 peptide containing acetyl-Lys and a coumarin fluorophore with a carbonate ester. By the simple addition of the probe to a HDAC solution, enzyme activity was clearly detected through spontaneous intramolecular transesterification, which renders the probe fluorescent. In addition, K4(Ac)-CCB can be applied to the evaluation of HDAC inhibitor activity. This is the first report to demonstrate the monitoring of HDAC activity by using a one-step procedure. Thus, our novel fluorogenic probe will provide a powerful tool for epigenetic research and the discovery of HDAC-targeted drugs.