7-amino-3-ethyl-4-methylcoumarin | 57584-51-7

• 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-amino-3-ethyl-4-methylcoumarin
• 英文别名: 7-Amino-3-ethyl-4-methyl-2H-chromen-2-one；7-amino-3-ethyl-4-methylchromen-2-one
• CAS: 57584-51-7
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: QELJSRMHQJVTAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-amino-3-ethyl-4-methylcoumarin 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以67%的产率得到7-acetylamino-3-ethyl-4-methylcoumarin
  参考文献：
  名称：

  Substrate specificity of acetoxy derivatives of coumarins and quinolones towards Calreticulin mediated transacetylation: Investigations on antiplatelet function

  摘要：

  Calreticulin transacetylase (CRTAase) is known to catalyze the transfer of acetyl group from polyphenolic acetates (PA) to certain receptor proteins (RP), thus modulating their activity. Herein, we studied for the first time the substrate specificity of CRTAase towards N-acetylamino derivatives of coumarins and quinolones. This study is endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. Among all the N-acetylamino/acetoxy coumarins and quinolones screened, 7-N-acetylamino-4-methylcoumarin (7-AAMC, 17) was found to be the superior substrate to platelet CRTAase and emerged as the most promising antiplatelet agent both in vitro and in vivo. Further it caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2), modulation of tissue factor and the inhibition of platelet aggregation. It was also found effective in the inhibition of LPS induced pro-thrombotic conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.016
• 作为产物：
  描述：

  (3-羟基-苯基)-氨基甲酸乙酯 在 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 7-amino-3-ethyl-4-methylcoumarin
  参考文献：
  名称：

  Substrate specificity of acetoxy derivatives of coumarins and quinolones towards Calreticulin mediated transacetylation: Investigations on antiplatelet function

  摘要：

  Calreticulin transacetylase (CRTAase) is known to catalyze the transfer of acetyl group from polyphenolic acetates (PA) to certain receptor proteins (RP), thus modulating their activity. Herein, we studied for the first time the substrate specificity of CRTAase towards N-acetylamino derivatives of coumarins and quinolones. This study is endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. Among all the N-acetylamino/acetoxy coumarins and quinolones screened, 7-N-acetylamino-4-methylcoumarin (7-AAMC, 17) was found to be the superior substrate to platelet CRTAase and emerged as the most promising antiplatelet agent both in vitro and in vivo. Further it caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2), modulation of tissue factor and the inhibition of platelet aggregation. It was also found effective in the inhibition of LPS induced pro-thrombotic conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.016

文献信息

• Novel Coumarin 7-Carboxamide/Sulfonamide Derivatives as Potential Fungicidal Agents: Design, Synthesis, and Biological Evaluation
  作者：Shu-Guang Zhang、Yu-Qiang Wan、Ya Wen、Wei-Hua Zhang

  DOI：10.3390/molecules27206904

  日期：——

  compounds have been used as fungicides for half a century, and dozens of varieties have been developed so far. This study focused on the introduction of carboxamide and sulfonamide moieties in a coumarin core to discover novel derivatives. Based on this strategy, we synthesized two series of novel carboxamide and sulfonamide substituted coumarin derivatives, and their fungicidal activity was also investigated

  香豆素类化合物具有抗肿瘤、抗凝血、抗HIV、抗真菌、杀虫等多种生物活性。酰胺类和磺胺类化合物作为杀菌剂已有半个世纪的历史，迄今已开发出几十个品种。这项研究的重点是在香豆素核心中引入羧酰胺和磺酰胺部分，以发现新的衍生物。基于此策略，我们合成了两个系列的新型羧酰胺和磺酰胺取代香豆素衍生物，并对其杀菌活性进行了研究。一些设计的化合物在初步试验中具有针对六种植物病原真菌的潜在活性，化合物6r突出显示。化合物6r表现出更强的杀真菌活性Botrytis cinerea (EC 50 = 20.52 µg/mL) 将成为进一步研究的主要结构。
• FLUORESCENT MOLECULE AND METHOD FOR DETECTING TARGET NUCLEIC ACID
  申请人：Riken

  公开号：EP2484671A1

  公开（公告）日：2012-08-08

  Provided are a fluorescent on/off switchable compound for a gene analysis, which is highly stable and highly sensitive, and enables amplification and observation of a trace gene signal, and a labeling reagent for detection of a bio-related material, which uses the fluorescent on/off switchable compound. A compound represented by the following formula (I'): wherein X is a hydrogen atom or a carboxylic acid-protecting group, Y is a 2,4-dinitrobenzenesulfonyl group, a 2-cyano-4-nitrobenzenesulfonyl group or a 5-nitropyridin-2-ylsulfonyl group, R1, R2, R3 and R4 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group having a carbon number of 1 to 6, an alkoxy group having a carbon number of 1 to 6, an aryl group having a carbon number of 6 to 10, or a cyano group.

  本发明提供了一种用于基因分析的荧光开关化合物，它具有高稳定性和高灵敏度，可放大和观察痕量基因信号，还提供了一种用于检测生物相关材料的标记试剂，该试剂使用了该荧光开关化合物。由下式（I'）表示的化合物： 其中 X 是氢原子或羧酸保护基团，Y 是 2，4-二硝基苯磺酰基、2-氰基-4-硝基苯磺酰基或 5-硝基吡啶-2-基磺酰基，R1、R2、R3 和 R4 各自独立地是氢原子、卤素原子、氢氧基原子、氢原子或氢原子、卤素原子、羟基、碳原子数为 1-6 的烷基、碳原子数为 1-6 的烷氧基、碳原子数为 6-10 的芳基或氰基。
• Substrate specificity of acetoxy derivatives of coumarins and quinolones towards Calreticulin mediated transacetylation: Investigations on antiplatelet function
  作者：Abha Kathuria、Nivedita Priya、Karam Chand、Prabhjot Singh、Anjali Gupta、Sarah Jalal、Shilpi Gupta、Hanumantharao G. Raj、Sunil K. Sharma

  DOI：10.1016/j.bmc.2011.11.016

  日期：2012.2

  Calreticulin transacetylase (CRTAase) is known to catalyze the transfer of acetyl group from polyphenolic acetates (PA) to certain receptor proteins (RP), thus modulating their activity. Herein, we studied for the first time the substrate specificity of CRTAase towards N-acetylamino derivatives of coumarins and quinolones. This study is endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. Among all the N-acetylamino/acetoxy coumarins and quinolones screened, 7-N-acetylamino-4-methylcoumarin (7-AAMC, 17) was found to be the superior substrate to platelet CRTAase and emerged as the most promising antiplatelet agent both in vitro and in vivo. Further it caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2), modulation of tissue factor and the inhibition of platelet aggregation. It was also found effective in the inhibition of LPS induced pro-thrombotic conditions. (C) 2011 Elsevier Ltd. All rights reserved.