4-prop-2-ynyl-7-methoxycoumarin | 128095-09-0

• 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-prop-2-ynyl-7-methoxycoumarin
• 英文别名: 7-Methoxy-4-prop-2-ynyloxy-chromen-2-one；7-methoxy-4-prop-2-ynoxychromen-2-one
• CAS: 128095-09-0
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: YSJVVNCKHKJXBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  48.67
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-prop-2-ynyl-7-methoxycoumarin 在 potassium carbonate 、 copper(II) sulfate 、 sodium ascorbate 、 potassium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 77.0h， 生成
  参考文献：
  名称：

  Photophysics of Coumarin and Carbostyril-Sensitized Luminescent Lanthanide Complexes: Implications for Complex Design in Multiplex Detection

  摘要：

  Luminescent lanthanide (Ln(III)) complexes with coumarin or carbostyril antennae were synthesized and their photophysical properties evaluated using steady-state and time-resolved UV-vis spectroscopy. Ligands bearing distant hydroxycoumarin-derived antennae attached through triazole linkers were modest sensitizers for Eu(III) and Tb(III), whereas ligands with 7-amidocarbostyrils directly linked to the coordination site could reach good quantum yields for multiple Ln(III), including the visible emitters Sm(III) and Dy(III), and the near-infrared emitters Nd(III) and Yb(III). The highest lanthanide-centered luminescence quantum yields were 35% (Tb), 7.9% (Eu), 0.67% (Dy), and 0.18% (Sm). Antennae providing similar luminescence intensities with 2-4 Ln-emitters were identified. Photoredox quenching of the carbostyril antenna excited states was observed for all Eu(III)-complexes and should be sensitizing in the case of Yb(III); the scope of the process extends to Ln(III) for which it has not been seen previously, specifically Dy(III) and Sm(III). The proposed process is supported by photophysical and electrochemical data. A FRET-type mechanism was identified in architectures with both distant and close antennae for all of the Lns. This mechanism seems to be the only sensitizing one at long distance and probably contributes to the sensitization at shorter distances along with the triplet pathway. The complexes were nontoxic to either bacterial or mammalian cells. Complexes of an ester-functionalized ligand were taken up by bacteria in a concentration-dependent manner. Our results suggest that the effects of FRET and photoredox quenching should be taken into consideration when designing luminescent Ln complexes. These results also establish these Ln(III)-complexes for multiplex detection beyond the available two-color systems.

  DOI：

  10.1021/jacs.6b11274
• 作为产物：
  描述：

  丹皮酚 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.5h， 生成 4-prop-2-ynyl-7-methoxycoumarin
  参考文献：
  名称：

  鬼臼毒素和香豆素的新型缀合物：合成，细胞毒性，细胞周期阻滞，结合CT DNA和抑制TopoIIβ。

  摘要：

  使用点击反应制备了一系列鬼臼毒素和香豆素的结合物，并评估了它们对A549，HepG2，HeLa和LoVo细胞的细胞毒性。其中，化合物14e对这些癌细胞表现出最强的细胞毒性，IC 50值为4.9-17.5μM。此外，14e通过调节LoVo细胞中的P21和Cyclin D1破坏了微管并诱导了G1期的细胞周期停滞。另外，14e结合CT DNA并选择性地抑制TopoIIβ优于TopoIIα。分子对接模型表明14e似乎与几个DNA碱基和残基Gln778形成稳定的氢键。综上所述，这些缀合物具有被开发为抗肿瘤药的潜力。

  DOI：

  10.1016/j.bmcl.2019.06.063

文献信息

• The Synthesis and Biological Evaluation of Aloe-Emodin-Coumarin Hybrids as Potential Antitumor Agents
  作者：Hai Shang、Yue Hu、Jingrong Li、Lingyu Li、Yu Tian、Xiaoxue Li、Qi Wu、Zhongmei Zou

  DOI：10.3390/molecules27196153

  日期：——

  A series of novel aloe-emodin–coumarin hybrids were designed and synthesized. The antitumor activity of these derivatives was evaluated against five human tumor cell lines (A549, SGC-7901, HepG2, MCF-7 and HCT-8). Some of the synthesized compounds exhibited moderate to good activity against one or more cell lines. Particularly, compound 5d exhibited more potent antiproliferative activity than the reference

  设计并合成了一系列新型芦荟-大黄素-香豆素混合物。针对五种人类肿瘤细胞系（A549、SGC-7901、HepG2、MCF-7 和 HCT-8）评估了这些衍生物的抗肿瘤活性。一些合成的化合物对一种或多种细胞系表现出中等至良好的活性。特别是，化合物5d对所有测试的肿瘤细胞系都表现出比参考药物依托泊苷更强的抗增殖活性，表明它具有广谱的抗肿瘤活性，并且它可能为进一步开发作为抗肿瘤药物的先导化合物提供有希望的结构。修改。此外，还进行了合成化合物的构效关系研究。
• Rao, Ch. Prasad; Srimannarayana, G., Synthetic Communications, 1990, vol. 20, # 4, p. 535 - 540
  作者：Rao, Ch. Prasad、Srimannarayana, G.

  DOI：——

  日期：——
• RAO, CH. PRASAD;SRIMANNARAYANA, G., SYNTH. COMMUN., 20,(1990) N, C. 535-540
  作者：RAO, CH. PRASAD、SRIMANNARAYANA, G.

  DOI：——

  日期：——