(3E)-2,3-dihydro-3-[(3,4-dihydroxyphenyl)methylene]-7-methoxy-4H-1-benzopyran-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: (3E)-2,3-dihydro-3-[(3,4-dihydroxyphenyl)methylene]-7-methoxy-4H-1-benzopyran-4-one
• 英文别名: (E)-3-(3,4-dihydroxybenzylidene)-7-methoxychroman-4-one；7-O-methyl-sappanone A；3-(3,4-dihydroxy-benzylidene)-7-methoxy-chroman-4-one；3-(3,4-Dihydroxy-benzyliden)-7-methoxy-chroman-4-on；(3E)-3-[(3,4-dihydroxyphenyl)methylidene]-7-methoxychromen-4-one
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: PJPVPNNIOZGDFS-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氯-1-(2,4-二羟基苯基)丙烷-1-酮 在 哌啶 、 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (3E)-2,3-dihydro-3-[(3,4-dihydroxyphenyl)methylene]-7-methoxy-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3-Benzylidene-4-chromanone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

  摘要：

  合成了一系列 3-亚苄基-4-色满酮衍生物（3-20），并评估了其抗氧化和抑制α-葡萄糖苷酶活性的结构-活性关系。在合成的化合物中，含有儿茶酚分子的化合物 5、13 和 18 显示出了强效的 1,1-二苯基-2-苦基肼（DPPH）自由基清除活性（5：EC50 13 µM；13：EC50 14 µM；18：EC50 13 µM）。化合物 12、14 和 18 显示出较高的α-葡萄糖苷酶抑制活性（12：IC50 15 µM；14：IC50 25 µM；18：IC50 28 µM）。化合物 18 同时显示了强效的 DPPH 自由基清除活性和 α-葡萄糖苷酶抑制活性。这些数据表明，3-亚苄基-4-色满酮衍生物（如化合物 18）可作为先导化合物，用于开发具有抗氧化活性的新型α-葡萄糖苷酶抑制剂。

  DOI：

  10.1248/cpb.c16-00327

文献信息

• Synthesis and Biological Evaluation of 3-Benzylidene-4-chromanone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors
  作者：Koichi Takao、Marimo Yamashita、Aruki Yashiro、Yoshiaki Sugita

  DOI：10.1248/cpb.c16-00327

  日期：——

  A series of 3-benzylidene-4-chromanone derivatives (3–20) were synthesized and the structure–activity relationships for antioxidant and α-glucosidase inhibitory activities were evaluated. Among synthesized compounds, compounds 5, 13, 18, which contain catechol moiety, showed the potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (5: EC50 13 µM; 13: EC50 14 µM; 18: EC50 13 µM). The compounds 12, 14, 18 showed higher α-glucosidase inhibitory activity (12: IC50 15 µM; 14: IC50 25 µM; 18: IC50 28 µM). The compound 18 showed both of potent DPPH radical scavenging and α-glucosidase inhibitory activities. These data suggest that 3-benzylidene-4-chromanone derivatives, such as compound 18, may serve as the lead compound for the development of novel α-glucosidase inhibitors with antioxidant activity.

  合成了一系列 3-亚苄基-4-色满酮衍生物（3-20），并评估了其抗氧化和抑制α-葡萄糖苷酶活性的结构-活性关系。在合成的化合物中，含有儿茶酚分子的化合物 5、13 和 18 显示出了强效的 1,1-二苯基-2-苦基肼（DPPH）自由基清除活性（5：EC50 13 µM；13：EC50 14 µM；18：EC50 13 µM）。化合物 12、14 和 18 显示出较高的α-葡萄糖苷酶抑制活性（12：IC50 15 µM；14：IC50 25 µM；18：IC50 28 µM）。化合物 18 同时显示了强效的 DPPH 自由基清除活性和 α-葡萄糖苷酶抑制活性。这些数据表明，3-亚苄基-4-色满酮衍生物（如化合物 18）可作为先导化合物，用于开发具有抗氧化活性的新型α-葡萄糖苷酶抑制剂。
• WO2008/67451
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and antioxidant properties of substituted 3-benzylidene-7-alkoxychroman-4-ones
  作者：Alireza Foroumadi、Alireza Samzadeh-Kermani、Saeed Emami、Gholamreza Dehghan、Maedeh Sorkhi、Fatemeh Arabsorkhi、Mahmoud Reza Heidari、Mohammad Abdollahi、Abbas Shafiee

  DOI：10.1016/j.bmcl.2007.10.034

  日期：2007.12

  A series of 3-benzylidene-7-alkoxychroman-4-one derivatives were synthesized and evaluated for their antioxidant activities. The antioxidant activity was assessed using three methods, namely, 1, 1 -diphenyl-2-picrylhydrazy] (DPPH) radical scavenging, ferric reducing antioxidant power (FRAP), and thiobarbituric acid reactive substances (TBARS) assays. 3-Benzylidene-7-alkoxychroman-4-one derivatives bearing catecholic group on benzylidene moiety exhibited excellent antioxidant activity. Compounds having catechol moiety exhibited potent antioxidant activities in all tested methods and they were more active than the reference drug, Trolox. (c) 2007 Elsevier Ltd. All rights reserved.
• Perkin; Ray; Robinson, Journal of the Chemical Society, 1927, p. 2100
  作者：Perkin、Ray、Robinson

  DOI：——

  日期：——
• REPORTER SYSTEM FOR HIGH THROUGHPUT SCREENING OF COMPOUNDS AND USES THEREOF
  申请人：RATAN Rajiv

  公开号：US20130005666A1

  公开（公告）日：2013-01-03

  The NF-E2-related factor 2 (Nrf2) is a key transcriptional regulator of antioxidant defense and detoxification. To directly monitor stabilization of Nrf2 we fused its Neh2 domain, responsible for the interaction with its nucleocytoplasmic regulator, Keap1, to firefly luciferase (Neh2-luciferase). It is shown herein that Neh2 domain is sufficient for recognition, ubiquitination and proteasomal degradation of Neh2-luciferase fusion protein. The novel Neh2-luc reporter system allows direct monitoring of the adaptive response to redox stress and classification of drugs based on the time-course of reporter activation. The novel reporter was used to screen a library of compounds to identify activators of Nrf2. The most robust and yet non toxic Nrf2 activators found—nordihydroguaiaretic acid, fisetin, and gedunin-induced astrocyte-dependent neuroprotection from oxidative stress via an Nrf2-dependent mechanism.