7-ethoxycarbonylmethoxy-3-(4-methoxyphenyl)-4H-chromen-4-one | 6760-95-8

• 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-ethoxycarbonylmethoxy-3-(4-methoxyphenyl)-4H-chromen-4-one
• 英文别名: ethyl 2-{[3-(4-methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxy}acetate；3-(4-methoxyphenyl)-7-ethoxyformylmethoxy-4H-chromen-4-one；Ethyl-4-methoxy-7-isoflavonoxyacetat；7-Ethoxycarbonylmethoxy-4'-methoxy-isoflavon；[3-(4-methoxy-phenyl)-4-oxo-4H-chromen-7-yloxy]-acetic acid ethyl ester；Ethyl 2-[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxyacetate
• CAS: 6760-95-8
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: AQGKQVSQXNYWTC-UHFFFAOYSA-N

物化性质

• 沸点：
  515.4±50.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-ethoxycarbonylmethoxy-3-(4-methoxyphenyl)-4H-chromen-4-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以71%的产率得到7-carboxymethoxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of Haptens and Conjugates for ELISAs of Phytoestrogens. Development of the Immunological Tests

  摘要：

  Seven carboxylic acid haptens of isoflavonoids were synthesized, with the spacer arm on the oxygen atom at the C7 position for one series, with formononetin, daidzein, equol, biochanin A, and genistein, and at the C8 position for a second series, with only formononetin and daidzein. The different haptens were coupled to bovine serum albumin (BSA) and to swine thyroglobulin (Thyr). Polyclonal antibodies were generated against the BSA conjugates. Enzyme-linked immunosorbent assays (ELISAs) were developed based on competition between free phytoestrogens and the Thyr-hapten conjugates for specific antibodies. IC50 values of the standard curves ranged between 0.8 and 20 ng/mL that is, 0.3 and 9.2 pmol/well. The antibodies obtained should be useful for assays in vegetable matter as well as in biological fluids after a separation step. These ELISAs should be valuable also in the food industry to control phytoestrogen concentrations prior to and after processing.

  DOI：

  10.1021/jf990896v
• 作为产物：
  描述：

  1-(2,4-二羟基苯基)-2-(4-甲氧基苯基)乙酮 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 14.0h， 生成 7-ethoxycarbonylmethoxy-3-(4-methoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  新型大豆苷元类似物和天冬氨酸体外抗流感活性

  摘要：

  基于中药（TCM）活性成分黄豆苷元的结构修饰合成了一系列新型异黄酮，并在体外评估了它们在MDCK细胞中对抗H1N1达菲耐药（H1N1 TR）病毒的抗流感活性线。其中，4-oxo-4H-1-benzopyran-8-carbaldehydes 11a-11g 是最有前途的，它们表现出与核苷类抗病毒剂利巴利文相比更好的活性和选择性。3-(4-Bromophenyl)-7-hydroxy-4-oxo-4H-1-benzopyran-8-carboxaldehyde (11c) 显示出最好的抑制活性 (EC50, 29.0 μM) 和选择性指数 (SI>10.3)。

  DOI：

  10.1002/cbdv.201400337

文献信息

• C-7 modified flavonoids as novel tyrosyl-tRNA synthetase inhibitors
  作者：Zhu-Ping Xiao、Wei Wei、Qi Liu、Peng-Fei Wang、Xing Luo、Fang-Yuan Chen、Yang Cao、Hong-Xia Huang、Mi-Mi Liu、Hai-Liang Zhu

  DOI：10.1039/c6ra28061g

  日期：——

  Twenty C-7 modified flavonoids were designed and synthesized.

  二十种经过改良的C-7类黄酮类化合物被设计并合成。
• Synthesis, characterization and biological evaluation of formononetin derivatives as novel EGFR inhibitors via inhibiting growth, migration and inducing apoptosis in breast cancer cell line
  作者：Hong-Yan Lin、Wen-Xue Sun、Chao-Sai Zheng、Hong-Wei Han、Xue Wang、Ya-Han Zhang、Han-Yue Qiu、Cheng-Yi Tang、Jin-Liang Qi、Gui-Hua Lu、Rong-Wu Yang、Xiao-Ming Wang、Yong-Hua Yang

  DOI：10.1039/c7ra09825a

  日期：——

  Novel formononetin derivative 4v inhibited MDA-MB-231 cell proliferation, migration and induced apoptosis through targeting EGFR.

  一种新型的异黄酮衍生物4v通过靶向EGFR抑制了MDA-MB-231细胞的增殖和迁移，并诱导了凋亡。
• Structural modification and antihypertensive activity study of formononetin derivatives
  作者：Sai-Jie Zuo、Dong-Lai Ma、Jing Li、Qiu-Hong Guo、Li Zhou

  DOI：10.1080/10286020.2021.2005588

  日期：2022.9.2
• Novel Daidzein Analogs and Their <i>in Vitro</i> Anti‐Influenza Activities
  作者：Shu‐Ting Chung、Yi‐Ting Huang、Hsin‐Yi Hsiung、Wen‐Hsin Huang、Chen‐Wen Yao、An‐Rong Lee

  DOI：10.1002/cbdv.201400337

  日期：2015.4

  series of novel isoflavonoids were synthesized based on structural modifications of daidzein, an active ingredient of traditional Chinese medicine (TCM) and evaluated for their anti‐influenza activity, in vitro, against H1N1 Tamiflu‐resistant (H1N1 TR) virus in the MDCK cell line. Among them, 4‐oxo‐4H‐1‐benzopyran‐8‐carbaldehydes 11a–11g were most promising, and they demonstrated better activities and selectivities

  基于中药（TCM）活性成分黄豆苷元的结构修饰合成了一系列新型异黄酮，并在体外评估了它们在MDCK细胞中对抗H1N1达菲耐药（H1N1 TR）病毒的抗流感活性线。其中，4-oxo-4H-1-benzopyran-8-carbaldehydes 11a-11g 是最有前途的，它们表现出与核苷类抗病毒剂利巴利文相比更好的活性和选择性。3-(4-Bromophenyl)-7-hydroxy-4-oxo-4H-1-benzopyran-8-carboxaldehyde (11c) 显示出最好的抑制活性 (EC50, 29.0 μM) 和选择性指数 (SI>10.3)。
• Synthesis of Haptens and Conjugates for ELISAs of Phytoestrogens. Development of the Immunological Tests
  作者：Catherine Bennetau-Pelissero、Cyril Le Houérou、Valérie Lamothe、Françoise Le Menn、Pierre Babin、Bernard Bennetau

  DOI：10.1021/jf990896v

  日期：2000.2.1

  Seven carboxylic acid haptens of isoflavonoids were synthesized, with the spacer arm on the oxygen atom at the C7 position for one series, with formononetin, daidzein, equol, biochanin A, and genistein, and at the C8 position for a second series, with only formononetin and daidzein. The different haptens were coupled to bovine serum albumin (BSA) and to swine thyroglobulin (Thyr). Polyclonal antibodies were generated against the BSA conjugates. Enzyme-linked immunosorbent assays (ELISAs) were developed based on competition between free phytoestrogens and the Thyr-hapten conjugates for specific antibodies. IC50 values of the standard curves ranged between 0.8 and 20 ng/mL that is, 0.3 and 9.2 pmol/well. The antibodies obtained should be useful for assays in vegetable matter as well as in biological fluids after a separation step. These ELISAs should be valuable also in the food industry to control phytoestrogen concentrations prior to and after processing.