3,7-二羟基-2-苯基-4H-苯并吡喃-4-酮 | 108238-40-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 3,7-二羟基-2-苯基-4H-苯并吡喃-4-酮
• 英文名称: 7,3'-dihydroxyflavone
• 英文别名: 3′,7-dihydroxyflavone；7,3’-dihydroxyflavone；3',7-dihydroxyflavone；7-hydroxy-2-(3-hydroxy-phenyl)-chromen-4-one；7-Hydroxy-2-(3-hydroxy-phenyl)-chromen-4-on；7-hydroxy-2-(3-hydroxyphenyl)chromen-4-one
• CAS: 108238-40-0
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: DYARIVMCYYQNNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

代谢

7,3p-二羟基黄酮已知的人类代谢物包括(2S,3S,4S,5R)-3,4,5-三羟基-6-[2-(3-羟基苯基)-4-氧代色酮-7-基]氧代氧杂环己烷-2-羧酸。

7,3p-Dihydroxyflavone has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-(3-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  3,7-二羟基-2-苯基-4H-苯并吡喃-4-酮 在 sodium carbonate 作用下， 生成 7-acetoxy-2-(3-methoxy-phenyl)-chromen-4-one
  参考文献：
  名称：

  花青素。第一部分：选择性甲基化和去甲基化

  摘要：

  DOI：

  10.1039/jr9540004065
• 作为产物：
  描述：

  7-methoxy-2-(3-methoxyphenyl)chroman-4-one 在 五氯化磷 、 氢碘酸 、 乙酸酐 、 苯 作用下， 生成 3,7-二羟基-2-苯基-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  Hattori, Acta Phytochimica, 1932, vol. 6, p. 131,152

  摘要：

  DOI：

文献信息

• Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches
  作者：Baojian Wu、Xiaoqiang Wang、Shuxing Zhang、Ming Hu

  DOI：10.1007/s11095-012-0666-z

  日期：2012.6

  Catalytic selectivity of human UGT1A9, an important membrane-bound enzyme catalyzing glucuronidation of xenobiotics, was determined experimentally using 145 phenolics and analyzed by 3D-QSAR methods. Catalytic efficiency of UGT1A9 was determined by kinetic profiling. Quantitative structure activity relationships were analyzed using CoMFA and CoMSIA techniques. Molecular alignment of substrate structures was made by superimposing the glucuronidation site and its adjacent aromatic ring to achieve maximal steric overlap. For a substrate with multiple active glucuronidation sites, each site was considered a separate substrate. 3D-QSAR analyses produced statistically reliable models with good predictive power (CoMFA: q2 = 0.548, r2 = 0.949, r pred 2  = 0.775; CoMSIA: q2 = 0.579, r2 = 0.876, r pred 2  = 0.700). Contour coefficient maps were applied to elucidate structural features among substrates that are responsible for selectivity differences. Contour coefficient maps were overlaid in the catalytic pocket of a homology model of UGT1A9, enabling identification of the UGT1A9 catalytic pocket with a high degree of confidence. CoMFA/CoMSIA models can predict substrate selectivity and in vitro clearance of UGT1A9. Our findings also provide a possible molecular basis for understanding UGT1A9 functions and substrate selectivity.

  通过实验使用145种酚类化合物，并通过3D-QSAR方法分析，确定了人UGT1A9的催化选择性。UGT1A9是一种重要的膜结合酶，催化外源性物质的葡糖醛酸化反应。通过动力学分析确定了UGT1A9的催化效率。使用CoMFA和CoMSIA技术分析了定量结构活性关系。通过将葡糖醛酸化位点及其相邻的芳香环重叠，实现了底物结构的最大立体重叠。对于具有多个活性葡糖醛酸化位点的底物，每个位点被视为单独的底物。3D-QSAR分析产生了统计上可靠的模型，具有良好的预测能力（CoMFA：q2=0.548，r2=0.949，r pred 2=0.775；CoMSIA：q2=0.579，r2=0.876，r pred 2=0.700）。通过轮廓系数图阐明了底物中负责选择性差异的结构特征。将轮廓系数图叠加在UGT1A9的同源模型的催化口袋中，能够高度自信地识别UGT1A9的催化口袋。CoMFA/CoMSIA模型可以预测底物的选择性和UGT1A9的体外清除率。我们的发现还提供了理解UGT1A9功能和底物选择性的可能分子基础。
• TRKB AGONISTS AND METHODS OF USE
  申请人：Ye Keqiang

  公开号：US20130040947A1

  公开（公告）日：2013-02-14

  Compounds and methods related to the activation of the TrkB receptor are provided. The methods include administering a 7,8-di-hydroxyflavone derivative with modified flavone or heterocyclic ring to a subject in need thereof. Methods and compounds for the treatment of disorders including neurologic disorders, neuropsychiatric disorders, and metabolic disorders (e.g., obesity) are provided.

  本文提供与TrkB受体激活相关的化合物和方法。这些方法包括将带有改性黄酮或杂环环的7,8-二羟基黄酮衍生物注射给需要的受试者。本文还提供了治疗神经系统疾病、神经精神疾病和代谢性疾病（例如肥胖症）的方法和化合物。
• Rubber composition and tire with rubber containing flavone
  申请人：The Goodyear Tire & Rubber Company

  公开号：EP2730431A1

  公开（公告）日：2014-05-14

  A rubber composition comprising a diene based elastomer and an adhesion promoter derived from a flavone, a methylene donor and a methylene acceptor is disclosed. The rubber composition is essentially free of cobalt. Also, a pneumatic tire comprising such a rubber composition is disclosed.

  本发明公开了一种橡胶组合物，该组合物包含一种二烯基弹性体和一种由黄酮、亚甲基供体和亚甲基受体衍生的附着力促进剂。该橡胶组合物基本上不含钴。此外，还公开了一种包含这种橡胶组合物的充气轮胎。
• 感染症の治療を目的としたフラボン類、クマリン類および関連化合物の使用
  申请人：プレンダーガスト、パトリック、ティ.

  公开号：JP2003504327A

  公开（公告）日：2003-02-04

  \n (57)【要約】\n本発明は感染症、特にウイルス（例えばHCV、HIV、ピコルナウイルスあるいは呼吸器ウイルス）あるいは寄生虫（例えばトキソプラズマ症）感染症の治療におけるシルシリオール、3'4'-ジアセトキシ-5,6,7-トリメトキシフラボンあるいはナリンギンなどのフラビン類の使用を提供する。また前記方法で使用するための組成物群も提供する。\n

  \(57) [Abstract] The invention provides for the use of silsiliol, 3'4'-diacetoxy-5,6,7-trimethoxyflavone or柚皮苷等黄素的用途。还提供了一组用于上述方法的组合物。\n
• Method of treating pain using agents that promote neuronal differentiation
  申请人：Rusanescu Gabriel

  公开号：US10398760B2

  公开（公告）日：2019-09-03

  The present invention is based on the seminal concept of treating pain by promoting neuronal differentiation. The invention provides a method of treating pain utilizing agents that induce neuronal differentiation by activating specific receptors. The invention also provides a method of screening of agents for the purpose of use in treating pain, based on their neuronal differentiation activity.

  本发明基于通过促进神经元分化来治疗疼痛的开创性概念。本发明提供了一种利用通过激活特定受体诱导神经元分化的制剂治疗疼痛的方法。本发明还提供了一种根据制剂的神经元分化活性筛选用于治疗疼痛的制剂的方法。