4-Hydroxy-3-(1-iminoethyl)coumarin | 91137-45-0

• 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: 4-Hydroxy-3-(1-iminoethyl)coumarin
• 英文别名: 4-hydroxy-3-iminoacetylcoumarin；3-ethanimidoyl-4-hydroxy-2H-chromen-2-one；3-iminoacetyl-4-hydroxycoumarin；JB032；3-(1-aminoethylidene)-2H-chromene-2,4-(3H)-dione；3-ethanimidoyl-4-hydroxychromen-2-one
• CAS: 91137-45-0
• 化学式: C₁₁H₉NO₃
• mdl: MFCD00458354
• 分子量: 203.197
• InChiKey: AXPPRQQWMUYKLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 4-Hydroxy-3-(1-iminoethyl)coumarin 以 二氯甲烷 、 异丙醇 为溶剂， 反应 24.0h， 以54.55%的产率得到[(η⁶-p-cymene)ruthenium(II)chlorido-3-(1-aminomethylene)-2H-chromeno-2,4-(3H)-dione-κ²-(N,O)]
  参考文献：
  名称：

  Spectroscopic and cytotoxic characteristics of (p-cymene)Ru(II) complexes with bidentate coumarins and density functional theory comparison with selected Pd(II) complexes

  摘要：

  This paper presents the synthesis of two new (p-cymene)-ruthenium(II) complexes 3a,b with the bidentate coumarin ligands 2a,b. Both complexes were characterized by FTIR spectroscopy, H-1 NMR, C-13 NMR, MS, elemental analysis and DFT calculations. The X-ray structure of complex 3a was also solved. The cytotoxic properties of both complexes were examined on human leukemia NALM-6 and HL-60 cells and melanoma WM-115 cells. The complexes possess higher cytotoxic activity than the ligands, but distinctive result is for complex 3b, which exhibited higher cytotoxic effect on WM-115 cells (IC50 = 60.2 +/- 7.8 mu M) in comparison to carboplatin (IC50 = 422.2 +/- 50.2 mu M). The results of DFT calculations performed at the BP86-D3/QZ4P level for Ru(II) complexes and Pd(II) complexes with the same ligands indicate that Pd(II) complexes are more lipophilic. Moreover the RP-TLC-Based Lipophilicity assessment was also performed. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2016.10.036
• 作为产物：
  描述：

  methyl 2-methylchromone-3-carboxylate 在 ammonium hydroxide 作用下， 反应 24.0h， 生成 4-Hydroxy-3-(1-iminoethyl)coumarin
  参考文献：
  名称：

  Spectroscopic and cytotoxic characteristics of (p-cymene)Ru(II) complexes with bidentate coumarins and density functional theory comparison with selected Pd(II) complexes

  摘要：

  This paper presents the synthesis of two new (p-cymene)-ruthenium(II) complexes 3a,b with the bidentate coumarin ligands 2a,b. Both complexes were characterized by FTIR spectroscopy, H-1 NMR, C-13 NMR, MS, elemental analysis and DFT calculations. The X-ray structure of complex 3a was also solved. The cytotoxic properties of both complexes were examined on human leukemia NALM-6 and HL-60 cells and melanoma WM-115 cells. The complexes possess higher cytotoxic activity than the ligands, but distinctive result is for complex 3b, which exhibited higher cytotoxic effect on WM-115 cells (IC50 = 60.2 +/- 7.8 mu M) in comparison to carboplatin (IC50 = 422.2 +/- 50.2 mu M). The results of DFT calculations performed at the BP86-D3/QZ4P level for Ru(II) complexes and Pd(II) complexes with the same ligands indicate that Pd(II) complexes are more lipophilic. Moreover the RP-TLC-Based Lipophilicity assessment was also performed. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2016.10.036

文献信息

• Synthesis and Evaluation of 4-Hydroxycoumarin Imines as Inhibitors of Class II Myosins
  作者：Jhonnathan Brawley、Emily Etter、Dante Heredia、Amarawan Intasiri、Kyle Nennecker、Joshua Smith、Brandon M. Welcome、Richard K. Brizendine、Thomas W. Gould、Thomas W. Bell、Christine Cremo

  DOI：10.1021/acs.jmedchem.0c01062

  日期：2020.10.8

  Inhibitors of muscle myosin ATPases are needed to treat conditions that could be improved by promoting muscle relaxation. The lead compound for this study ((3-(N-butylethanimidoyl)ethyl)-4-hydroxy-2H-chromen-2-one; BHC) was previously discovered to inhibit skeletal myosin II. BHC and 34 analogues were synthesized to explore structure–activity relationships. The properties of analogues, including solubility

  需要肌肉肌球蛋白 ATP 酶抑制剂来治疗可以通过促进肌肉放松来改善的病症。本研究的先导化合物（（3-（N-丁基乙酰亚胺酰基）乙基）-4-羟基-2 H - chromen -2-one；BHC）先前被发现可抑制骨骼肌球蛋白II。合成了 BHC 和 34 种类似物以探索结构-活性关系。类似物的特性，包括溶解性、稳定性和毒性，表明 BHC 支架可用于开发治疗方法。快骨骼肌和心肌肌球蛋白II，抑制骨骼肌收缩力的肌动蛋白活化的ATP酶活性的抑制离体，和减慢在体外测量了肌动蛋白滑动速度。与 BHC 相比，具有芳香侧臂的几种类似物对骨骼肌球蛋白与心脏肌球蛋白的效力（半数最大抑制浓度 (IC 50 ) <1 μM）和选择性（≥12 倍）均有所提高。几种类似物阻断了神经传递，表明它们对非肌肉肌球蛋白 II 的选择性高于骨骼肌球蛋白。竞争和分子对接研究表明 BHC 和 blebbistatin 结合到肌球蛋白的同一位点。
• A four-component Pfitzinger reaction: synthesis of 2-pyronylquinolin-4-carbamides
  作者：Sorayya Yaghoubi Kalurazi、Kurosh Rad-Moghadam、Shahram Moradi

  DOI：10.1007/s11164-017-2885-8

  日期：2017.8

  Abstract A one-pot route was developed for efficient synthesis of novel 2-substituted quinolin-4-carboxamides via a four-component sequential reaction between isatins, ammonium acetate, triethyl orthoacetate, and 4-hydroxycoumarin or 4-hydroxy-6-methyl-2H-pyran-2-one. This protocol is an extension of Pfitzinger’s quinoline synthesis and involves an unprecedented in situ iminoacetylation of 2H-pyrone

  摘要 通过一锅法，通过靛红，乙酸铵，原乙酸三乙酯和4-羟基香豆素或4-羟基-6-甲基-2之间的四组分顺序反应，可以有效合成新型的2-取代的喹啉-4-羧酰胺。H-吡喃-2-一。该方案是普菲青格（Pfitzinger）喹啉合成的扩展，涉及2 H-吡喃酮环在3位上空前的原位亚氨基乙酰化，随后依次进行Isatin开环和重排的环化反应。产物是喹啉-4-羧酰胺和4-羟基香豆素/ 4-羟基-6-甲基-2 H-吡喃-2-酮杂环的共价键对，其结构由其NMR，IR和质谱数据支持。 图形概要
• Synthesis, Crystal Structure and Biological Characterization of a Novel Palladium( <scp>II</scp> ) Complex with a Coumarin‐Derived Ligand
  作者：Elzbieta Budzisz、Bernhard K. Keppler、Gerald Giester、Magdalena Wozniczka、Aleksander Kufelnicki、Barbara Nawrot

  DOI：10.1002/ejic.200400483

  日期：2004.11

  for the formation of a palladium(II) complex. The structures of the ligand and its palladium complex 3 were determined by IR and 1H NMR spectroscopy, FAB mass spectrometry and elemental analysis. The single-crystal X-ray structure of 3 was also solved. Ligand 2 in 20% dioxane solution shows two protonation constants — log β11 = 4.28 ± 0.01 and log β12 = 7.66 ± 0.03. In complex 3 two ligand molecules

  2-甲基-4-氧代-4H-色烯-3-羧酸甲酯(1)用25%氨水处理得到3-(1-氨基亚乙基)-2H-色烯-2,4(3H)-二酮(2 ）。化合物 2 用作形成钯 (II) 络合物的配体。配体及其钯配合物3的结构通过IR和1H NMR光谱、FAB质谱和元素分析确定。还解析了 3 的单晶 X 射线结构。20% 二恶烷溶液中的配体 2 显示两个质子化常数 - log β11 = 4.28 ± 0.01 和 log β12 = 7.66 ± 0.03。在复合物 3 中，两个配体分子通过它们的 N 和 O 供体螯合到 Pd 离子上，得到一个带有顺式 N2O2 供体组的四配位 PdII 中心。PdII 处的配位几何形状是方平面，具有从 Pd 原子到配位原子的距离的典型值。在三个癌细胞系上测定了化合物 3 的细胞毒性。A546、HeLa 和 K562 细胞的 IC50 值分别为 9.7、7.8 和 7.8
• Somogyi, Laszlo; Sohar, Pal, Liebigs Annalen, 1995, # 10, p. 1903 - 1906
  作者：Somogyi, Laszlo、Sohar, Pal

  DOI：——

  日期：——
• Spectroscopic and cytotoxic characteristics of (p-cymene)Ru(II) complexes with bidentate coumarins and density functional theory comparison with selected Pd(II) complexes
  作者：Anna Skoczynska、Karin Lux、Peter Mayer、Ingo-Peter Lorenz、Urszula Krajewska、Marek Rozalski、Anna Dołęga、Elzbieta Budzisz

  DOI：10.1016/j.ica.2016.10.036

  日期：2017.2

  This paper presents the synthesis of two new (p-cymene)-ruthenium(II) complexes 3a,b with the bidentate coumarin ligands 2a,b. Both complexes were characterized by FTIR spectroscopy, H-1 NMR, C-13 NMR, MS, elemental analysis and DFT calculations. The X-ray structure of complex 3a was also solved. The cytotoxic properties of both complexes were examined on human leukemia NALM-6 and HL-60 cells and melanoma WM-115 cells. The complexes possess higher cytotoxic activity than the ligands, but distinctive result is for complex 3b, which exhibited higher cytotoxic effect on WM-115 cells (IC50 = 60.2 +/- 7.8 mu M) in comparison to carboplatin (IC50 = 422.2 +/- 50.2 mu M). The results of DFT calculations performed at the BP86-D3/QZ4P level for Ru(II) complexes and Pd(II) complexes with the same ligands indicate that Pd(II) complexes are more lipophilic. Moreover the RP-TLC-Based Lipophilicity assessment was also performed. (C) 2016 Elsevier B.V. All rights reserved.