5,7-dimethoxy-2-(pyridin-4'-yl)-4H-chromen-4-one | 6344-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5,7-dimethoxy-2-(pyridin-4'-yl)-4H-chromen-4-one
• 英文别名: 5,7-Dimethoxy-2-pyridin-4-yl-4H-chromen-4-one；5,7-dimethoxy-2-pyridin-4-ylchromen-4-one
• CAS: 6344-93-0
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: FJOGVHKRNRHTLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-dimethoxy-2-(pyridin-4'-yl)-4H-chromen-4-one 在 aluminum (III) chloride 作用下， 以 乙腈 为溶剂， 以75%的产率得到5-hydroxy-7-methoxy-2-(pyridin-4-yl)-4H-chromen-4-one
  参考文献：
  名称：

  Design, Synthesis, Biological Evaluation, and Molecular Docking of Novel Benzopyran and Phenylpyrazole Derivatives as Akt Inhibitors

  摘要：

  By inspiration of good Akt1 inhibitory and cytotoxic activity of our previously screened hits 1 and 2, a series of novel benzopyrans 3a–c, 4 and phenylpyrazoles 5a–c, 6a–b, and 7 were designed, synthesized, and biologically evaluated for their in vitro Akt1 inhibitory and cytotoxic activity. The results revealed that all of these compounds showed moderate‐to‐excellent antiproliferative effects against the tested cancer cell lines (i.e. HL‐60, OVCAR, PC‐3, and HepG2). Among them, compounds 3a and 3c exhibited preferable Akt1 inhibitory activities (IC50 of 3a and 3c are 6.18 and 5.28 μm, respectively), while compounds 4, 5a–c, 6a–b, and 7 only showed weak Akt1 inhibitory activities. Consequently, we used molecular docking and dynamic simulation to propose a mode of binding between Akt1 and the 3c compound.

  DOI：

  10.1111/cbdd.12489
• 作为产物：
  描述：

  1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-pyrid-4-ylpropan-1,3-dion 在 硫酸 作用下， 以 氯仿 为溶剂， 生成 5,7-dimethoxy-2-(pyridin-4'-yl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of Heterocyclic-Substituted Chromones and Chalcones

  摘要：

  DOI：

  10.1021/jo01070a039

文献信息

• Flavonoid-based inhibitors of the Phi-class glutathione transferase from black-grass to combat multiple herbicide resistance
  作者：Maria Schwarz、Rebecca F. M. Eno、Stefanie Freitag-Pohl、Christopher R. Coxon、Hannah E. Straker、David J. Wortley、David J. Hughes、Glynn Mitchell、Jenny Moore、Ian Cummins、Nawaporn Onkokesung、Melissa Brazier-Hicks、Robert Edwards、Ehmke Pohl、Patrick G. Steel

  DOI：10.1039/d1ob01802g

  日期：——

  discovered a specific flavonoid as a natural ligand of the recombinant enzyme. A series of related synthetic flavonoids was prepared and their binding to AmGSTF1 was investigated showing a high affinity for derivatives bearing a O-5-decyl-α-carboxylate. Molecular modelling based on high-resolution crystal structures allowed a binding pose to be defined which explained flavonoid binding specificity.

  禾本科杂草多重除草剂抗性（MHR）的进化和增长继续威胁着全球谷物生产。虽然多种过程可能导致耐药性，但早期的工作已将 phi 类谷胱甘肽-S-转移酶 ( Am GSTF1) 确定为黑草 ( Alopecurus myosuroides ) 中 MHR 的功能性生物标志物。这项研究结合化学和结构生物学，进一步深入了解Am GSTF1 在 MHR 中的作用。获得了野生型Am GSTF1 的晶体结构，以及两个专门设计的变体，这些变体允许与Am GSTF1 抑制剂 4-氯-7-硝基-苯并呋喃 (NBD-Cl) 的谷胱甘肽和谷胱甘肽加合物进行共晶结构测定。这些研究表明NBD-Cl的抑制活性与活性位点的封闭和底物结合的阻碍有关。使用配体钓鱼实验寻找Am GSTF1 的其他选择性抑制剂，确定了许多黄酮类化合物作为潜在的配体。随后使用黑草提取物进行的实验发现了一种特定的黄酮类化合物作为重组酶的天然配体。制备
• Pharmaceutical Compositions for the Prevention and Treatment of Complex Diseases and Their Delivery by Insertable Medical Devices
  申请人：Wong Norman C.W.

  公开号：US20090029987A1

  公开（公告）日：2009-01-29

  The present invention relates to polyphenol-like compounds that are useful for inhibiting VCAM-1 expression, MCP-1 expression and/or SMC proliferation in a mammal. The disclosed compounds are useful for regulating markers of inflammatory conditions, including vascular inflammation, and for treatment and prevention of inflammatory and cardiovascular diseases and related disease states.

  本发明涉及一种类似于多酚化合物，可用于抑制哺乳动物中VCAM-1表达、MCP-1表达和/或SMC增殖。所披露的化合物可用于调节炎症状态的标志物，包括血管炎症，并用于治疗和预防炎症和心血管疾病及相关疾病状态。
• Synthesis of Heterocyclic-Substituted Chromones and Chalcones
  作者：PATRICK F. DEVITT、ANITA TIMONEY、MICHAEL A. VICKARS

  DOI：10.1021/jo01070a039

  日期：1961.12
• Pharmaceutical compositions for the prevention and treatment of complex diseases and their delivery by insertable medical devices
  申请人：Resverlogix, Inc

  公开号：EP2314295B1

  公开（公告）日：2015-01-28
• US8410109B2
  申请人：——

  公开号：US8410109B2

  公开（公告）日：2013-04-02