4-hydroxy-3-((4-hydroxy-2-oxo-2H-chromen-3-yl)(2,3-dimethoxyphenyl)methyl)-2H-chromen-2-one | 115604-40-5

• 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: 4-hydroxy-3-((4-hydroxy-2-oxo-2H-chromen-3-yl)(2,3-dimethoxyphenyl)methyl)-2H-chromen-2-one
• 英文别名: 3,3′-((2′′,3′′-dimethoxyphenyl)methylene)bis(4-hydroxy-2Hchromen-2-one)；3,3'-((2,3-dimethoxyphenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)；(2,3-dimethoxy-phenyl)-bis-(4-hydroxy-2-oxo-2H-chromen-3-yl)-methane；(2,3-Dimethoxy-phenyl)-bis-(4-hydroxy-2-oxo-2H-chromen-3-yl)-methan；3-[(2,3-dimethoxyphenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-4-hydroxy-2H-chromen-2-one；3-[(2,3-dimethoxyphenyl)-(4-hydroxy-2-oxochromen-3-yl)methyl]-4-hydroxychromen-2-one
• CAS: 115604-40-5
• 化学式: C₂₇H₂₀O₈
• mdl: MFCD01543801
• 分子量: 472.451
• InChiKey: TWRZXJUDMNMATE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-((4-hydroxy-2-oxo-2H-chromen-3-yl)(2,3-dimethoxyphenyl)methyl)-2H-chromen-2-one 在 吡啶 、 乙酸酐 作用下， 生成 7-(2,3-dimethoxy-phenyl)-7H-pyrano[3,2-c;5,6-c'] dichromium ene-6,8-dione
  参考文献：
  名称：

  Eckstein et al., Roczniki Chemii, 1958, vol. 32, p. 801,805, 806

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基香豆素 、 2,3-二甲氧基苯甲醛 以 乙醇 为溶剂， 反应 3.0h， 以72%的产率得到4-hydroxy-3-((4-hydroxy-2-oxo-2H-chromen-3-yl)(2,3-dimethoxyphenyl)methyl)-2H-chromen-2-one
  参考文献：
  名称：

  4-羟基香豆素衍生物的合成，结构，毒理学和药理研究。

  摘要：

  合成了二十种4-羟基香豆素衍生物。其中五个是第一次描述。3,3'-（2,3,4-三甲氧基苯基亚甲基）双-（4-羟基-2H-1-苯并吡喃-2-酮）（7）和3,3'-（3的X射线晶体结构分析，（5-二甲氧基-4-羟基苯基亚甲基）双-（4-羟基-2H-1-苯并吡喃-2-酮）（9）证实了这些化合物的结构。对华法林抗凝作用的比较药理研究表明，合成的化合物具有不同的抗凝活性。最有前景的化合物是3,3'-（4-氯苯基亚甲基）双-（4-羟基-2H-1-苯并吡喃-2-酮）（12），具有低毒性，非常好的吸收指数和剂量依赖性抗凝活性。

  DOI：

  10.1016/j.ejmech.2006.03.007

文献信息

• A novel nanomagnetic solid acid catalyst for the synthesis of new functionalized bis‐coumarin derivatives under microwave irradiations in green conditions
  作者：Zhila Zare‐Akbari、Siavoush Dastmalchi、Ladan Edjlali、Leila Dinparast、Moosa Es'haghi

  DOI：10.1002/aoc.5649

  日期：2020.7

  water under microwave irradiation conditions. Scanning electron microscopy, transmission electron microscopy, energy‐dispersive X‐ray spectroscopy, X‐ray diffraction, thermogravimetric analysis, dynamic light scattering, vibrating sample magnetometry, Fourier transform infrared spectroscopy, UV–visible absorption, and Brunauer‐Emmett‐Teller (BET) techniques confirmed the successful synthesis of the

  在这项研究中，基于磺基水杨酸固定在Fe 3 O 4纳米颗粒（Fe 3 O 4上）上的新型，绿色，环保和磁性异构催化剂报道了磺基水杨酸MNP）。使用1当量的芳基醛与2当量的4-羟基香豆素在微波辐射条件下反应，可以高收率合成双香豆素类似物。扫描电子显微镜，透射电子显微镜，能量色散X射线光谱法，X射线衍射，热重分析，动态光散射，振动样品磁力分析法，傅立叶变换红外光谱法，紫外可见吸收和Brunauer-Emmett-Teller（BET ）技术证实了催化剂的成功合成。提出的绿色方案的主要吸引人的特点是反应时间非常短（10-15分钟），产率极高，并且避免了有害或有毒的试剂和溶剂。耐热性强，易于分离，
• Visible Light-Induced Synthesis of Biscoumarin Analogs under Catalyst-Free Conditions
  作者：Ankusab Noorahmadsab Nadaf、Kalegowda Shivashankar

  DOI：10.1002/jhet.3171

  日期：2018.6

  Biscoumarin analogs were synthesized by the reaction between two equivalent of 4‐hydroxycoumarin and one equivalent of aryl aldehydes induced by visible light [22 W compact fluorescent lamp (CFL) bulb]. This new method is simple, cost‐effective, and furnished excellent yields with broad substrate generality in short reaction time.

  Biscoumarin类似物是通过可见光[22 W紧凑型荧光灯（CFL）灯泡]诱导的两当量4-羟基香豆素与一当量芳基醛之间的反应合成的。这种新方法简单，经济高效，并且在短反应时间内即可提供优异的收率，并具有广泛的底物通用性。
• Bis-coumarins; non-cytotoxic selective urease inhibitors and antiglycation agents
  作者：Uzma Salar、Arsalan Nizamani、Fizza Arshad、Khalid Mohammed Khan、Muhammed Imran Fakhri、Shahnaz Perveen、Nessar Ahmed、M. Iqbal Choudhary

  DOI：10.1016/j.bioorg.2019.103170

  日期：2019.10

  The current study is concerned with the identification of lead molecules based on the bis-coumarin scaffold having selective urease inhibitory and antiglycation activities. For that purpose, bis-coumarins (1-44) were synthesized and structurally characterized by different spectroscopic techniques. Eight derivatives 4, 8-10, 14, 17, 34, and 40 demonstrated urease inhibition in the range of IC50=4.4 +/- 0.21-115.6 +/- 2.13 mu M, as compared to standard thiourea (IC50=21.3 +/- 1.3 mu M). Especially, compound 17 (IC50=4.4 +/- 0.21 mu M) was found to be five-fold more potent than the standard. Kinetic studies were also performed on compound 17 in order to identify the mechanism of inhibition. Kinetic studies revealed that compound 17 is a competitive inhibitor. Antiglycation activity was evaluated using glycation of bovine serum albumin by methylglyoxal in vitro. Compounds 2, 11-13, 16, 17, 19-22, 35, 37, and 42 showed good to moderate antiglycation activities with IC50 values of 333.63-919.72 mu M, as compared to the standard rutin (IC50=294.46 +/- 1.5 mu M). Results of both assays showed that the compounds with urease inhibitory activity did not show any antiglycation potential, and vice versa. Only compound 17 showed dual inhibition potential. All compounds were also evaluated for cytotoxicity. Compounds 17, 19, and 37 showed a weak toxicity towards 3 T3 mouse fibroblast cell line. All other compounds were found to be non-cytotoxic. Urease inhibition is an approach to treat infections caused by ureolytic bacteria whereas inhibition of glycation of proteins is a strategy to avoid late diabetic complications. Therefore, these compounds may serve as leads for further research.