7-羟基-3-甲基-2-苯基-4H-1-苯并吡喃-4-酮 | 18651-15-5

• 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: 7-羟基-3-甲基-2-苯基-4H-1-苯并吡喃-4-酮
• 中文别名: 7-羟基-3-甲基-2-苯基色酮；7-羟基-3-甲基黄酮
• 英文名称: 7-hydroxy-3-methylflavone
• 英文别名: 3-methyl-7-hydroxyflavone；7-hydroxy-3-methyl-2-phenylchromone；7-hydroxy-3-methyl-2-phenyl-chromen-4-one；7-Hydroxy-3-methyl-2-phenyl-chromen-4-on；7-hydroxy-3-methyl-2-phenylchromen-4-one
• CAS: 18651-15-5
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: SUNCCQBNDWHMPR-UHFFFAOYSA-N

物化性质

• 熔点：
  278°C
• 沸点：
  452.2±45.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

7-羟基-3-甲基黄酮已知的人体代谢物包括(2S,3S,4S,5R)-3,4,5-三羟基-6-(3-甲基-4-氧代-2-苯基色烯-7-基)氧杂环己烷-2-羧酸。

7-Hydroxy-3-methylflavone has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(3-methyl-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid.

来源:NORMAN Suspect List Exchange

安全信息

• 海关编码：
  2914400090

制备方法与用途

用途：回苏灵的中间体。

生产方法：通过间苯二酚在氯化锌的催化作用下与丙酸缩合生成2,4-二羟基苯丙酮，再将后者与苯甲酰氯及苯甲酸在200℃高温条件下环合制得该产品。

反应信息

• 作为反应物：
  描述：

  7-羟基-3-甲基-2-苯基-4H-1-苯并吡喃-4-酮 在 乙酸酐 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 30.0h， 生成 7-acetoxy-8-(1',1'-dimethylallyl)-3-methylflavone
  参考文献：
  名称：

  Subba Raju, K. V.; Sudha, K.; Srimannarayana, G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 10, p. 866 - 870

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲氧基-3-甲基-2-苯基-4H-苯并-g-吡喃酮 在 氢溴酸 、 溶剂黄146 作用下， 生成 7-羟基-3-甲基-2-苯基-4H-1-苯并吡喃-4-酮
  参考文献：
  名称：

  732.通过重排邻乙酰氧基苯乙酮合成3-取代的色酮

  摘要：

  DOI：

  10.1039/jr9520003826

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。
• [EN] NOVEL IMAGING AGENTS FOR DETECTING NEUROLOGICAL DYSFUNCTION<br/>[FR] NOUVEAUX AGENTS D'IMAGERIE POUR LA DÉTECTION D'UNE DYSFONCTION NEUROLOGIQUE
  申请人：SIEMENS MEDICAL SOLUTIONS

  公开号：WO2009102498A1

  公开（公告）日：2009-08-20

  Disclosed here in are compounds and methods of diagnosing Alzheimer's Disease or a predisposition thereto in a mammal, the method comprising administering to the mammal a diagnostically effective amount of a radiolabeled compound, wherein the compound is selected from the group consisting of radiolabeled flavones, coumarins, carbazoles, quinolinones, chromenones, imidazoles and triazoles derivatives, allowing the compound to distribute into the brain tissue, and imaging the brain tissue, wherein an increase in binding of the compound to the brain tissue compared to a normal control level of binding indicates that the mammal is suffering from or is at risk of developing Alzheimer's Disease

  本文披露了一种在哺乳动物中诊断阿尔茨海默病或其易感性的化合物和方法，该方法包括向哺乳动物投与一种放射标记化合物的诊断有效量，所述化合物选自放射标记黄酮类、香豆素类、咔唑类、喹诺酮类、色酮类、咪唑类和三唑类衍生物组成的群体，使化合物分布到脑组织中，并对脑组织进行成像，其中与正常控制水平的结合相比，化合物对脑组织的结合增加表明哺乳动物患有或有发展阿尔茨海默病的风险
• Novel derivatives of flavones, xanthones and coumarins
  申请人：——

  公开号：US20020183318A1

  公开（公告）日：2002-12-05

  A marked up versions of the abstract showing insertions and deletions are included in Appendix A. Please add the following abstract: Compounds having the formula (I) Z—OCH 2 —C≡CCH 2 —NRR 1 (I) or a pharmaceutically acceptable salt or solvate thereof wherein Z can represent the formula (1A) or (1B). 1 The compounds possess antiproliferative activity and are useful as modulators of multiple drug resistance in cancer chemotherapy. The compounds may also be useful for the manufacture of a medicament for the treatment or prevention of neoplasms, menopausal disorders and osteoporosis.

  摘要的标记版本，显示插入和删除，已包含在附录A中。请添加以下摘要：具有化学式(I)Z—OCH2—C≡CCH2—NRR1(I)或其药用可接受的盐或溶剂，其中Z可以表示化学式(1A)或(1B)。这些化合物具有抗增殖活性，并可用作癌症化疗中多药耐药的调节剂。这些化合物还可能用于制造用于治疗或预防肿瘤、更年期障碍和骨质疏松症的药物。
• Synthesis and biological evaluation of novel flavone/triazole/benzimidazole hybrids and flavone/isoxazole-annulated heterocycles as antiproliferative and antimycobacterial agents
  作者：Yerrabelly Jayaprakash Rao、Thummala Sowjanya、Gogula Thirupathi、Nandula Yadagiri Sreenivasa Murthy、Sudha Sravanti Kotapalli

  DOI：10.1007/s11030-018-9833-4

  日期：2018.11

  AbstractA series of new flavone/isoxazole fused heterocycles 5a–f and flavone/1,2,3-triazole/benzimidazole hybrid heterocycles compounds 7a–t were synthesized via an intramolecular cyclization and Cu(I)-catalyzed click 1,3-dipolar cycloaddition. The products were evaluated for their antiproliferative activity against human breast cancer cell line (MCF-7) using sulforhodamine B assay (SRB) and antimycobacterial

  摘要通过分子内环化和Cu（I）催化的点击1,3-偶极环加成反应合成了一系列新的黄酮/异恶唑稠合杂环5a-f和黄酮/ 1,2,3-三唑/苯并咪唑杂合杂环化合物7a-t。使用磺基罗丹明B测定（SRB）评估了产品对人乳腺癌细胞系（MCF-7）的抗增殖活性，并使用浊度测定法评估了产品的抗分枝杆菌活性。大多数测试化合物显示出抗增殖活性和抗分枝杆菌活性。化合物7l，7q和7r显示出中等的抗增殖活性，IC50值为 17.9、14.2、19.1（\ upmu \ hbox M} \）分别地，化合物5a和化合物5a在30 （\ upmu \ hbox M} \）浓度下显示出中等的抗分枝杆菌活性，抑制率为41.7％  。 图形概要
• A tandem synthesis of 3-aroylcoumarinoflavones catalyzed by l-proline and their antioxidant activity
  作者：G. Thirupathi、E. Yadaiah Goud、Y. Hemasri、MD. Suban Ali、Y. Jayaprakash Rao

  DOI：10.1007/s13738-016-0995-7

  日期：2017.2

  efficient and high-yielding synthesis of 3-aroylcoumarinoflavones has been developed by the condensation of easily synthesized 7-hydroxy-8-formylflavones and benzoyl acetonitriles in the presence of catalytic amount of l-proline in ethanol reflux. All the synthesized compounds were evaluated for their antioxidant activity. Some of the compounds showed very good activity compared to standard BHT.

  通过在乙醇回流中催化量的1-脯氨酸的存在下，通过容易合成的7-羟基-8-甲酰基黄酮与苯甲酰基乙腈的缩合，已经开发了一种容易，方便，有效且高产的3-芳酰基香豆素黄酮合成方法。评价所有合成的化合物的抗氧化活性。与标准BHT相比，某些化合物显示出非常好的活性。