methyl-2-[(2-oxo-2H-1-benzopyran-3-carbonyl)amino]propanoate | 56159-51-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl-2-[(2-oxo-2H-1-benzopyran-3-carbonyl)amino]propanoate
• 英文别名: methyl 2-[(2-oxo-2H-chromene-3-carbonyl)amino]propanoate；N-(3-Cumarinylcarbonyl)-L-alaninmethylester；methyl (2S)-2-[(2-oxochromene-3-carbonyl)amino]propanoate
• CAS: 56159-51-4
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: LZMMGMVQKLBUNL-QMMMGPOBSA-N

物化性质

• 熔点：
  108-110 °C
• 沸点：
  529.0±50.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl-2-[(2-oxo-2H-1-benzopyran-3-carbonyl)amino]propanoate 在 sodium hydroxide 、 potassium hydrogensulfate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (S)-2-[(2-oxo-2H-chromen-3-ylcarbonyl)amino]propanoic acid
  参考文献：
  名称：

  Novel emissive bio-inspired non-proteinogenic coumarin-alanine amino acid: fluorescent probe for polyfunctional systems

  摘要：

  Two new bio-inspired non-proteinogenic compounds L1 and L2, containing coumarin and/or acridine chromophores and bearing as spacer an alanine amino acid were successfully synthesized and fully characterized by elemental analysis, H-1 and C-13 NMR, infrared spectroscopy (KBr discs), melting point, ESI-TOF (electrospray ionization-time of flight-mass), UV-vis absorption and emission spectroscopy, fluorescence quantum yields and lifetime measurements. A relative fluorescence quantum yield of 0.02 was determined for both compounds. In L2 the presence of an intramolecular energy transfer from the coumarin to the acridine unit was observed. L1 and L2 are quite sensitive to the basicity of the environment. At alkaline values both compounds show a strong quenching in the fluorescence emission, attributed to the photoinduced electron transfer (PET). However, both deprotonated forms recover the emission with the addition of Zn2+, Cd2+ and Al3+ metal ions. As multifunctional emissive probes, the titration of L1 and L2 with lanthanides (III), Eu3+ and Tb3+ was also explored as new visible bio-probes in the absence and in the presence of liposomes. In a liposomal environment a lower energy transfer was observed.

  DOI：

  10.1007/s00726-012-1262-6
• 作为产物：
  描述：

  水杨醛 在 哌啶 、 N-甲基吗啉 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 methyl-2-[(2-oxo-2H-1-benzopyran-3-carbonyl)amino]propanoate
  参考文献：
  名称：

  香豆素-氨基酸衍生物的有效一锅合成作为潜在的抗炎和抗氧化剂

  摘要：

  摘要 合成了一系列七种香豆素-氨基酸酯缀合物，并通过核磁共振（1H 和 13C）和质谱进行了表征。此外，研究了这些化合物的治疗应用，例如抗炎和抗氧化活性。在合成的化合物中，大多数类似物与标准品相比表现出良好的效率。图形概要

  DOI：

  10.1080/00397911.2020.1735442

文献信息

• An efficient one-pot synthesis of coumarin-amino acid derivatives as potential anti-inflammatory and antioxidant agents
  作者：Mamata Devendra Naik、Yadav D. Bodke、Vijay Kumar M、Revanasiddappa BC

  DOI：10.1080/00397911.2020.1735442

  日期：2020.4.17

  Abstract A series of seven coumarinyl-amino acid ester conjugates have been synthesized and characterized by NMR (1H and 13C) and mass spectra. Further, the compounds were investigated for their therapeutic applications such as anti-inflammatory and antioxidant activities. Among the synthesized compounds most of the analogs showed good efficiency compared with the standard. Graphical Abstract

  摘要 合成了一系列七种香豆素-氨基酸酯缀合物，并通过核磁共振（1H 和 13C）和质谱进行了表征。此外，研究了这些化合物的治疗应用，例如抗炎和抗氧化活性。在合成的化合物中，大多数类似物与标准品相比表现出良好的效率。图形概要
• Novel emissive bio-inspired non-proteinogenic coumarin-alanine amino acid: fluorescent probe for polyfunctional systems
  作者：Elisabete Oliveira、José Luis Capelo、João Carlos Lima、Carlos Lodeiro

  DOI：10.1007/s00726-012-1262-6

  日期：2012.10

  Two new bio-inspired non-proteinogenic compounds L1 and L2, containing coumarin and/or acridine chromophores and bearing as spacer an alanine amino acid were successfully synthesized and fully characterized by elemental analysis, H-1 and C-13 NMR, infrared spectroscopy (KBr discs), melting point, ESI-TOF (electrospray ionization-time of flight-mass), UV-vis absorption and emission spectroscopy, fluorescence quantum yields and lifetime measurements. A relative fluorescence quantum yield of 0.02 was determined for both compounds. In L2 the presence of an intramolecular energy transfer from the coumarin to the acridine unit was observed. L1 and L2 are quite sensitive to the basicity of the environment. At alkaline values both compounds show a strong quenching in the fluorescence emission, attributed to the photoinduced electron transfer (PET). However, both deprotonated forms recover the emission with the addition of Zn2+, Cd2+ and Al3+ metal ions. As multifunctional emissive probes, the titration of L1 and L2 with lanthanides (III), Eu3+ and Tb3+ was also explored as new visible bio-probes in the absence and in the presence of liposomes. In a liposomal environment a lower energy transfer was observed.
• Facile Synthesis of Some Coumarin Derivatives and Their Cytotoxicity through VEGFR2 and Topoisomerase II Inhibition
  作者：Mohamed S. Gomaa、Ibrahim A. I. Ali、Gaber El Enany、El Sayed H. El Ashry、Samir M. El Rayes、Walid Fathalla、Abdulghany H. A. Ahmed、Samar A. Abubshait、Haya A. Abubshait、Mohamed S. Nafie

  DOI：10.3390/molecules27238279

  日期：——

  Novel semisynthetic coumarin derivatives were synthesized to be developed as chemotherapeutic anticancer agents through topoisomerase II, VEGFR2 inhibition that leads to apoptotic cancer cell death. The coumarin amino acids and dipeptides derivatives were prepared by the reaction of coumarin-3-carboxylic acid with amino acid methyl esters following the N,N-dicyclohexylcarbodiimide (DCC) method and

  合成了新型半合成香豆素衍生物，通过拓扑异构酶 II、VEGFR2 抑制导致癌细胞死亡，将其开发为化疗抗癌剂。采用N,N-二环己基碳二亚胺(DCC)法，以1-羟基-苯并三唑(HOBt)为偶联剂，通过香豆素-3-羧酸与氨基酸甲酯的反应制备香豆素氨基酸和二肽衍生物。合成的化合物针对 VEGFR2 和拓扑异构酶 IIα 蛋白进行筛选，以突出它们的结合亲和力和虚拟结合机制。有趣的是，化合物 4k (Tyr) 和 6c (β-Ala-L-Met) 通过与关键氨基酸（如共结晶配体）形成相同的相互作用而共享对三种蛋白质的活性。化合物 4k 和 6c 均对 MCF-7 细胞表现出有效的细胞毒活性，IC50 值为 4.98 和 5.85 µM，分别导致细胞死亡 97.82% 和 97.35%。验证分子对接研究，与索拉非尼 (30 µM) 相比，两种化合物均表现出良好的 VEGFR-2 抑制作用，IC50 值为