p-nitrophenyl 7-diethylaminocoumarin-3-carboxylate | 1038533-93-5

• 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: p-nitrophenyl 7-diethylaminocoumarin-3-carboxylate
• 英文别名: 4-nitrophenyl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate
• CAS: 1038533-93-5
• 化学式: C₂₀H₁₈N₂O₆
• 分子量: 382.373
• InChiKey: KMFQIZKXQOMGEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  102.89
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 7-diethylaminocoumarin-3-carboxylate 、 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以49%的产率得到
  参考文献：
  名称：

  用于基于 FRET 的磷脂酶 A2 酶动力学研究的混合链磷脂酰胆碱的合成，包括香豆素荧光团

  摘要：

  磷脂酶 A 2 (PLA 2 ) 酶催化甘油磷脂的sn -2 酯键的水解以产生脂肪酸和溶血磷脂。大量哺乳动物磷脂酶包含一个分泌型 PLA 2酶家族，存在于特定组织和细胞位置，具有独特的酶学特性和独特的生物学功能。开发新的实时荧光分光光度计 PLA 2测定应促进体外同工酶的动力学表征和机理阐明，具有检测和测量催化 PLA 2的潜在适用性组织和细胞位置的活性。在这里，我们报告了双标记磷脂酰胆碱类似物的新合成，其链端报告基团包括香豆素荧光团，用于基于荧光共振能量转移 (FRET) 的 PLA 2动力学研究酶。与第一代荧光磷脂供体-受体对相比，香豆素衍生物作为荧光标记物的使用为报告基团提供了显着减小的大小。该设计的主要优点是较少干扰酰基链的理化性质，从而提高合成探针的底物质量。为了评估荧光团取代基对催化水解和测定的脂水界面中磷脂堆积的影响，我们使用实验确定的蜂毒磷脂酶 A 2 的比活性作为分泌型 PLA

  DOI：

  10.1016/j.chemphyslip.2013.05.003
• 作为产物：
  描述：

  4-(二乙氨基)水杨醛 在 哌啶 、 三乙胺 、 potassium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 7.0h， 生成 p-nitrophenyl 7-diethylaminocoumarin-3-carboxylate
  参考文献：
  名称：

  Evaluation of Synthesized Ester or Amide Coumarin Derivatives on Aromatase Inhibitory Activity

  摘要：

  Aromatase inhibitors are effective for the treatment of diseases such as breast cancer, which has led to an increase in their demand. However, only a limited number of aromatase inhibitor drugs are currently being marketed. In addition, considering the important aspect of drug resistance, the development of newer drug types is required. We have been developing inhibitors with backbone structures that differ from existing aromatase inhibitors. In this regard, we previously reported that diethylaminocoumarin dimers and thiazolyl coumarin derivatives possess strong aromatase inhibiting capabilities. In this study, we further examined the structure activity relationships of coumarin derivatives synthesized from thiazolyl coumarin derivatives and their aromatase inhibiting capabilities. Consequently, amide coumarin N-benzhydry1-7-(diethylamino)2-oxo-2H-chromene-3-carboxamide (IC50 values 4.5 mu M) is inhibitor of aromatase. This inhibitor was found to be comparable aromatase inhibitory activity to the 1st generation aromatase inhibitor aminoglutethimide (3.2 mu M). Substitution of the amide group on the amide coumarin derivative affects the aromatase inhibiting activity. Our findings suggest that the structure of each substituent changes the orientation of the compound in the active site of aromatase, thus creating a difference in their activities.

  DOI：

  10.1248/bpb.b20-00035

文献信息

• Mono-acylation of a polyamine-β-cyclodextrin based on guest mediated acyl migration
  作者：Rodolfo F. Gómez-Biagi、Mark Nitz

  DOI：10.1039/c1cc12646f

  日期：——

  The S → N acylation rates of thioester functionalized coumarins on heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-cyclodextrin were measured. A high yield of mono-acylation was achieved with products that form self-inclusion compounds. The differential fluorescence response of the functionalized cyclodextrins upon binding biomacromolecules shows the potential of the constructs as probes.

  测定了硫酯功能化香豆素在全-6-脱氧-6-(2-氨基乙硫基)-β-环糊精上的南-北酰化速率。获得了高产率的一酰化产物，这些产物形成了自包合物。功能化环糊精在结合生物大分子时表现出不同的荧光响应，表明这些构筑体具有作为探针的潜力。
• Synthesis of phosphatidylcholine analogues derived from glyceric acid: a new class of biologically active phospholipid compounds
  作者：Renato Rosseto、Celize M. Tcacenco、Radha Ranganathan、Joseph Hajdu

  DOI：10.1016/j.tetlet.2008.03.084

  日期：2008.5

  Synthesis of a new class of phosphatidylcholine analogues derived from glyceric acid is reported for spectroscopic studies of phospholipases and conformation of phospholipid side-chains in biological membranes, using fluorescence resonance energy transfer (FRET) techniques.

  据报道，使用荧光共振能量转移 (FRET) 技术合成了一类新的源自甘油的磷脂酰胆碱类似物，用于磷脂酶和生物膜中磷脂侧链构象的光谱研究。
• Synthesis of phospholipids on a glyceric acid scaffold: design and preparation of phospholipase A2 specific substrates
  作者：Renato Rosseto、Joseph Hajdu

  DOI：10.1016/j.tet.2014.03.054

  日期：2014.5

  Synthesis of a new series of phospholipid analogues to serve as activity-based probes of secretory phospholipase A2 enzymes is reported. The synthesis is based upon (1) preparation of long-chain esters and amides of glyceric acid, followed by (2) regioselective derivatization of the diol function of the molecule to achieve phosphorylation at the primary hydroxyl group, and to introduce the incipient

  合成了一系列新的磷脂类似物，用作分泌型磷脂酶 A 2酶的活性探针。该合成基于 (1) 甘油酸的长链酯和酰胺的制备，然后 (2) 分子的二醇官能团的区域选择性衍生化以实现伯羟基的磷酸化，并引入初始的sn -目标化合物的2-酯基团。该序列已被证明允许掺入荧光、顺磁性和氧化还原活性报告基团，从而产生适用于检测和测量酶活性的磷脂类似物，以开发高度特异性、实时的磷脂酶 A 2光谱分析酶，以及跟踪水解产物的代谢归宿。该合成方法具有很大的灵活性，为其他磷脂代谢酶的活性探针的设计和合成开辟了道路。