7-hydroxy-3-(3',4'-dihydroxyphenyl)coumarin | 24043-79-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-hydroxy-3-(3',4'-dihydroxyphenyl)coumarin
• 英文别名: 3-(3,4-dihydroxyphenyl) 7-hydroxycoumarine；7-hydroxy-3-(3,4-dihydroxyphenyl)-coumarin；3-(3,4-dihydroxyphenyl)-7-hydroxycoumarin；3-(3,4-dihydroxy-phenyl)-7-hydroxy-chromen-2-one；3-(3,4-dihydroxyphenyl)-7-hydroxy-coumarin；3-<3,4-Dihydroxy-phenyl>-7-hydroxy-cumarin；3-(3,4-Dihydroxyphenyl)-7-hydroxychromen-2-one
• CAS: 24043-79-6
• 化学式: C₁₅H₁₀O₅
• 分子量: 270.241
• InChiKey: YASVZYJJTIRXLS-UHFFFAOYSA-N

物化性质

• 沸点：
  597.3±50.0 °C(Predicted)
• 密度：
  1.548±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-hydroxy-3-(3',4'-dihydroxyphenyl)coumarin 、 2(3),9(10),16(17),23(24)-tetra(2,3-dihydro-1H-inden-5-yloxy)phthalocyaninatotitanium(IV) oxide 以 四氢呋喃 为溶剂， 反应 3.0h， 以83%的产率得到3-(3-(3,4-dioxyphenyl)-7-hydroxycoumarino)-2(3),9(10),16(17),23(24)-tetra(2,3-dihydro-1H-inden-5-yloxy)phthalocyaninatotitanium(IV)
  参考文献：
  名称：

  Synthesis, characterization and dielectric properties of novel axial coumarin-substituted titanium(IV) phthalocyanines

  摘要：

  The oxotitanium(IV) phthalocyanine (2) and axial coumarin-substituted derivatives (5 and 6) have been synthesized, and characterized by IR, UV-Vis, fluorescence, H-1 NMR, MALDI-TOF mass spectrometry and elemental analysis. It was observed that the reaction of novel oxotitanium(IV) phthalocyanine with orthodihyroxycoumarin compounds gives its derivatives, substituted by coumarin at the axial position. The electronic and interface state density properties of the Ag/Pc/p-Si diodes have been investigated by current-voltage (I-V) and conductance-frequency-voltage (G-omega-V) methods. It was found that, the conduction mechanism of the diodes is controlled by the thermoionic emission mechanism. From the analysis of frequency, omega, dependence of electrical conductivity, sigma(ac), it was found that the sigma(ac) obeys the power law given by sigma(ac), = sigma(0)w(s). The interface state density of the diodes were determined from (G/omega)-omega plots. It was found that the kind of substitution affects both the interface and omega electrical properties of the phthalocyanine complexes considerably. The obtained results show that the Ag/6/p-Si heterojunction is a good candidate for the electronic device applications. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.09.055
• 作为产物：
  描述：

  3,4-二羟基苯乙酮 在 吗啉 、 乙酸酐 、 对甲苯磺酸 、 sulfur 、 三乙胺 作用下， 反应 8.17h， 生成 7-hydroxy-3-(3',4'-dihydroxyphenyl)coumarin
  参考文献：
  名称：

  3-芳基香豆素衍生物作为潜在抗糖尿病药的合成及生物学评价

  摘要：

  抽象的 通过微波辐射加热合成了多种取代的3-芳基香豆素衍生物。该方法具有环境友好，经济，分离纯化工艺简单，副产物少，反应收率高的特点。筛选了那些3-芳基香豆素衍生物的抗氧化剂，α-葡萄糖苷酶抑制物和晚期糖基化终产物（AGEs）形成抑制物。大多数化合物表现出显着的抗氧化剂和AGEs形成抑制活性。抗糖尿病活性研究表明，化合物11和17在体内与标准药物glibenclamide等效。根据实验结果，目标化合物35可用作开发抗糖尿病新药的先导化合物。整个实验表明，抗糖尿病活性在3-芳基香豆素中普遍存在，为抗糖尿病活性药物的开发增加了新的天然骨架。

  DOI：

  10.1080/14756366.2018.1518958

文献信息

• Synthesis and biological evaluation of 3-arylcoumarins as potential anti-Alzheimer's disease agents
  作者：Jie Yang、Pingping Zhang、Yuheng Hu、Teng Liu、Jie Sun、Xiaojing Wang

  DOI：10.1080/14756366.2019.1574297

  日期：2019.1.1

  the extremely complex pathogenesis. Accumulating evidence indicates there is a close relationship between several enzymes and Alzheimer's disease. Various substituted 3-arylcoumarin derivatives were synthesised, and their in vitro activity, including cholinesterase inhibitory activity, monoamine oxidase inhibitory activity, and antioxidant activity were investigated. Most of the compounds exhibited

  抽象的 阿尔茨海默氏病是一种神经退行性疾病，其发病机理极为复杂。越来越多的证据表明，几种酶与阿尔茨海默氏病之间存在密切的关系。合成了各种取代的3-芳基香豆素衍生物，并研究了它们的体外活性，包括胆碱酯酶抑制活性，单胺氧化酶抑制活性和抗氧化活性。大多数化合物表现出高活性。因此3-芳基香豆素类化合物具有治疗阿尔茨海默氏病的潜力。
• Synthesis and biological evaluation of hydroxylated 3-phenylcoumarins as antioxidants and antiproliferative agents
  作者：Jie Yang、Guo-Yun Liu、Fang Dai、Xiao-Yan Cao、Yan-fei Kang、Li-Mei Hu、Jiang-Jiang Tang、Xiu-Zhuang Li、Yan Li、Xiao-Ling Jin、Bo Zhou

  DOI：10.1016/j.bmcl.2011.08.090

  日期：2011.11

  Based on the observed biological activities of coumarins and resveratrol, we synthesized fourteen hydroxylated 3-phenylcoumarins (stilbene-coumarin hybrids) including six novel ortho-hydroxy-methoxy substituted derivatives, 1-14, by Perkin reaction. We characterized these compounds concerning their antioxidant activity against 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced pBR322 DNA strand breakage, and their antiproliferative effects on human promyelocytic leukemia HL-60 and human lung adenocarcinoma epithelial A549 cells. Structure-activity relationship information suggests that the introduction of ortho-hydroxy-methoxy groups and ortho-dihydroxy groups on the aromatic A ring could efficiently improve antiproliferative activity. Interestingly, a new derivative, 6-methoxy-7-hydroxy-3-(4'-hydroxyphenyl)coumarin, 9, behaved as a poor antioxidant but appeared to be the most potent antiproliferative agent among the compounds examined, and this activity was mediated by deregulation in cell cycle and induction of apoptosis. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of 3-arylcoumarin derivatives as potential anti-diabetic agents
  作者：Yuheng Hu、Bing Wang、Jie Yang、Teng Liu、Jie Sun、Xiaojing Wang

  DOI：10.1080/14756366.2018.1518958

  日期：2019.1.1

  Abstract A variety of substituted 3-arylcoumarin derivatives were synthesised through microwave radiation heating. The method has characteristics of environmental friendliness, economy, simple separation, and purification process, less by-products and high reaction yield. Those 3-arylcoumarin derivatives were screened for antioxidant, α-glucosidase inhibitory and advanced glycation end-products (AGEs)

  抽象的 通过微波辐射加热合成了多种取代的3-芳基香豆素衍生物。该方法具有环境友好，经济，分离纯化工艺简单，副产物少，反应收率高的特点。筛选了那些3-芳基香豆素衍生物的抗氧化剂，α-葡萄糖苷酶抑制物和晚期糖基化终产物（AGEs）形成抑制物。大多数化合物表现出显着的抗氧化剂和AGEs形成抑制活性。抗糖尿病活性研究表明，化合物11和17在体内与标准药物glibenclamide等效。根据实验结果，目标化合物35可用作开发抗糖尿病新药的先导化合物。整个实验表明，抗糖尿病活性在3-芳基香豆素中普遍存在，为抗糖尿病活性药物的开发增加了新的天然骨架。
• Synthesis, characterization and dielectric properties of novel axial coumarin-substituted titanium(IV) phthalocyanines
  作者：Selçuk Altun、Ahmet Altındal、Mustafa Bulut

  DOI：10.1016/j.poly.2012.09.055

  日期：2013.1

  The oxotitanium(IV) phthalocyanine (2) and axial coumarin-substituted derivatives (5 and 6) have been synthesized, and characterized by IR, UV-Vis, fluorescence, H-1 NMR, MALDI-TOF mass spectrometry and elemental analysis. It was observed that the reaction of novel oxotitanium(IV) phthalocyanine with orthodihyroxycoumarin compounds gives its derivatives, substituted by coumarin at the axial position. The electronic and interface state density properties of the Ag/Pc/p-Si diodes have been investigated by current-voltage (I-V) and conductance-frequency-voltage (G-omega-V) methods. It was found that, the conduction mechanism of the diodes is controlled by the thermoionic emission mechanism. From the analysis of frequency, omega, dependence of electrical conductivity, sigma(ac), it was found that the sigma(ac) obeys the power law given by sigma(ac), = sigma(0)w(s). The interface state density of the diodes were determined from (G/omega)-omega plots. It was found that the kind of substitution affects both the interface and omega electrical properties of the phthalocyanine complexes considerably. The obtained results show that the Ag/6/p-Si heterojunction is a good candidate for the electronic device applications. (c) 2012 Elsevier Ltd. All rights reserved.