5,7-dihydroxy-2-phenyl-6-(piperidin-2-yl)-4H-chromen-4-one | 91147-12-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 5,7-dihydroxy-2-phenyl-6-(piperidin-2-yl)-4H-chromen-4-one
• 英文别名: N-demethylcapitavine；5,7-dihydroxy-2-phenyl-6-piperidin-2-ylchromen-4-one
• CAS: 91147-12-5
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: QNAISVUYZYHGLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,4,5-四氢吡啶 、 白杨素 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以87%的产率得到5,7-dihydroxy-2-phenyl-6-(piperidin-2-yl)-4H-chromen-4-one
  参考文献：
  名称：

  酚类曼尼希反应一步法合成哌啶-2-基和吡咯烷-2-基黄酮类生物碱

  摘要：

  通过白杨素与环状亚胺或亚胺盐的高度区域选择性酚类曼尼希反应，实现了哌啶-2-基和吡咯烷-2-基黄酮类生物碱的高效一步合成，收率良好至极好。在不存在外部试剂的情况下在 H2O/THF 的混合物中进行反应，仅提供 C-6 烷基化产物。在 NaOH 存在下在水中的相同反应提供 C-8 烷基化黄酮类化合物作为主要产物。该反应已成功扩展到简单的酚类。

  DOI：

  10.1002/ejoc.201101312

文献信息

• Synthesis of novel flavonoid alkaloids as α-glucosidase inhibitors
  作者：Jing Zhen、Yujie Dai、Tom Villani、Daniel Giurleo、James E. Simon、Qingli Wu

  DOI：10.1016/j.bmc.2017.07.055

  日期：2017.10

  A series of novel flavonoid alkaloids were synthesized with different flavonoids and attached nitrogen-containing moieties. These new compounds were screened for inhibitory activity of α-glucosidase, among which compound 23 was found to show the lowest IC50 of 4.13 μM. Kinetic analysis indicates that the synthesized compounds 15 and 23 inhibit the enzyme in a non-competitive model with Ki value of

  合成了一系列具有不同类黄酮和连接的含氮部分的新型类黄酮生物碱。筛选了这些新化合物对α-葡萄糖苷酶的抑制活性，其中发现化合物23的最低IC 50为4.13μM。动力学分析表明，在具有Ki的非竞争性模型中，合成的化合物15和23抑制了该酶。值分别为37.8±0.8μM和13.2±0.6μM。进一步的对接研究表明，优选的结合口袋靠近催化中心，与实验结果相关。结构活性关系研究（SAR）表明，类黄酮结构中的4'-羟基和4位羰基对该生物活性很重要。在环A上添加额外的氢键和疏水基团将增加抑制活性。
• NOVEL PEPERIDINE-FLAVAN ALKALOID COMPOUNDS DERIVED FROM AFRICAN HERB TEA KINKELIBA AS ANTI-DIABETIC AGENTS
  申请人：Simon James E.

  公开号：US20130143921A1

  公开（公告）日：2013-06-06

  This invention provides the methods of separation and identification of a novel type of piperidine flavan alkaloids from an African herbal tea, the leaves of Combretum micranthum commonly known as kinkeliba, and the procedures for preparing the total piperidine flavan alkaloids (TPFA). In particular, this invention relates to the use of the plant extract that may contain TPFA as anti-diabetic agents in treatment of metabolic disorders and other applications related to this new chemical structure and derivatives thereof.

  这项发明提供了一种从非洲草药茶Combretum micranthum（通常称为kinkeliba）的叶子中分离和鉴定一种新型哌啶类黄烷生物碱的方法，以及制备总哌啶类黄烷生物碱（TPFA）的程序。特别地，该发明涉及使用可能含有TPFA的植物提取物作为抗糖尿病药物治疗代谢紊乱和其他与该新化学结构及其衍生物相关的应用。
• Peperidine-flavan alkaloid compounds derived from African herb tea kinkeliba as anti-diabetic agents
  申请人：Simon James E.

  公开号：US08642769B2

  公开（公告）日：2014-02-04

  This invention provides the methods of separation and identification of a novel type of piperidine flavan alkaloids from an African herbal tea, the leaves of Combretum micranthum commonly known as kinkeliba, and the procedures for preparing the total piperidine flavan alkaloids (TPFA). In particular, this invention relates to the use of the plant extract that may contain TPFA as anti-diabetic agents in treatment of metabolic disorders and other applications related to this new chemical structure and derivatives thereof.

  本发明提供了一种从非洲草药茶，即常称为kinkeliba的Combretum micranthum叶中分离和鉴定一种新型吡啶类黄烷生物碱的方法，以及制备总吡啶类黄烷生物碱（TPFA）的程序。特别地，本发明涉及使用可能含有TPFA的植物提取物作为治疗代谢紊乱和其他与此新化学结构及其衍生物相关应用的抗糖尿病剂。
• Synthesis, Biological Evaluation, and Molecular Modeling of Natural and Unnatural Flavonoidal Alkaloids, Inhibitors of Kinases
  作者：Thanh Binh Nguyen、Olivier Lozach、Georgiana Surpateanu、Qian Wang、Pascal Retailleau、Bogdan I. Iorga、Laurent Meijer、Françoise Guéritte

  DOI：10.1021/jm201727w

  日期：2012.3.22

  The screening of the ICSN chemical library on various disease-relevant protein kinases led to the identification of natural flavonoidal alkaloids of unknown configuration as potent inhibitors of the CDK1 and CDK5 kinases. We thus developed an efficient and modular synthetic strategy for their preparation and that of analogues in order to determine the absolute configuration of the active natural flavonoidal alkaloids and to provide further insights on the structure-activity relationships in this series. The structural determinants of the interaction between some flavonoidal alkaloids with specific kinases were also evaluated using molecular modeling.
• An Efficient One-Step Synthesis of Piperidin-2-yl and Pyrrolidin-2-yl Flavonoid Alkaloids through Phenolic Mannich Reactions
  作者：Thanh Binh Nguyen、Qian Wang、Françoise Guéritte

  DOI：10.1002/ejoc.201101312

  日期：2011.12

  An efficient one-step synthesis of piperidin-2-yl and pyrrolidin-2-yl flavonoid alkaloids was achieved in good to excellent yields by a highly regioselective phenolic Mannich reaction of chrysin with cyclic imines or iminium salts. Performing the reaction in a mixture of H2O/THF in the absence of an external reagent afforded the C-6 alkylated product exclusively. The same reaction in water in the presence

  通过白杨素与环状亚胺或亚胺盐的高度区域选择性酚类曼尼希反应，实现了哌啶-2-基和吡咯烷-2-基黄酮类生物碱的高效一步合成，收率良好至极好。在不存在外部试剂的情况下在 H2O/THF 的混合物中进行反应，仅提供 C-6 烷基化产物。在 NaOH 存在下在水中的相同反应提供 C-8 烷基化黄酮类化合物作为主要产物。该反应已成功扩展到简单的酚类。