5,6,7-trihydroxy-8-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-2-phenyl-4H-chromen-4-one | 1104858-60-7

• 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: 5,6,7-trihydroxy-8-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-2-phenyl-4H-chromen-4-one
• 英文别名: 5,6,7-trihydroxy-8-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]-2-phenylchromen-4-one
• CAS: 1104858-60-7
• 化学式: C₂₂H₂₄N₂O₆
• 分子量: 412.442
• InChiKey: KYFNKYFJYIRZBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-羟乙基哌嗪 、 聚合甲醛 、 黄芩素 以 甲醇 、 水 为溶剂， 反应 8.0h， 生成 5,6,7-trihydroxy-8-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  设计，合成，生物学评估和新型黄酮类化合物作为H3R抑制剂的分子对接

  摘要：

  设计，合成和评估了一系列新颖的黄酮衍生物的H 3 R抑制活性。结果显示四种化合物显示出显着的抗H 3 R活性。分子对接实验表明，盐桥，氢键和疏水相互作用都促进了抑制剂与H 3 R之间的相互作用。

  DOI：

  10.1111/cbdd.12981

文献信息

• CYCLIN-DEPENDENT PROTEIN KINASES INHIBITORS OF SCUTELLARIA FLAVONOID ORGANIC AMINE DERIVATIVES, SYNTHESIS AND USE THEREOF
  申请人：Zhang Shixuan

  公开号：US20100197619A1

  公开（公告）日：2010-08-05

  The present invention provides a series of cyclin-dependent protein kinases (Cdks) inhibitors, Scutellaria flavonoid organic amine derivatives, synthesis and use thereof. The preparation method is as follows: taking Baicalein (or Wogonin) from Scutellaria baicalensis as lead compound, mixting it with formaldehyde solution and organic amine compounds based on the molar ratio of 1:1-1.2:1-1.2, adding methanol of duplicate weight than baicalein and reacting at 50-70° C., filtering the sediment and washing and then drying so as to get the product with a content of not less than 97% (weight). Similar to Flavopiridol and P276-00, the activity of baicalein organic amine derivatives inhibiting Cdks has an increase of 50 times compared with that of Baicalin. It can selectively induce apoptosis of the proliferative phase cancer cells, which has scarcely any influence to the normal structure, and it belongs to anticancer drugs of cell cycle inhibitor kind. The product has a rich source of raw materials and has simple process, high purity, low cost, clear metabolic mechanism, high efficiency and low toxicity, which can be made into oral preparations or injections together with acid salts and is expected to become high efficient and low toxicity anti-cancer and AIDS drugs.

  本发明提供了一系列依赖于细胞周期蛋白激酶（Cdks）的抑制剂，即黄芩黄酮有机胺衍生物，其合成和使用方法。制备方法如下：以黄芩中的黄芩素（或黄芩苷）为引物化合物，与甲醛溶液和有机胺化合物按摩尔比1:1-1.2:1-1.2混合，加入重量为黄芩素两倍的甲醇，在50-70°C下反应，过滤沉淀并洗涤，然后干燥以得到含量不低于97%（重量）的产品。类似于Flavopiridol和P276-00，黄芩素有机胺衍生物抑制Cdks的活性比黄芩苷增加了50倍。它可以选择性地诱导增殖期癌细胞的凋亡，对正常结构几乎没有影响，属于细胞周期抑制剂类的抗癌药物。该产品具有丰富的原材料来源和简单的工艺，高纯度，低成本，代谢机制清晰，效率高，毒性低，可以与酸盐一起制成口服制剂或注射剂，预计将成为高效低毒的抗癌和艾滋病药物。
• Cyclin-dependent protein kinases inhibitors of Scutellaria flavonoid organic amine derivatives, synthesis and use thereof
  申请人：Zhang Shixuan

  公开号：US08377895B2

  公开（公告）日：2013-02-19

  The present invention provides a series of cyclin-dependent protein kinases (Cdks) inhibitors, Scutellaria flavonoid organic amine derivatives, synthesis and use thereof. The preparation method is as follows: taking Baicalein (or Wogonin) from Scutellaria baicalensis as lead compound, mixting it with formaldehyde solution and organic amine compounds based on the molar ratio of 1:1-1.2:1-1.2, adding methanol of duplicate weight than baicalein and reacting at 50-70° C., filtering the sediment and washing and then drying so as to get the product with a content of not less than 97% (weight). Similar to Flavopiridol and P276-00, the activity of baicalein organic amine derivatives inhibiting Cdks has an increase of 50 times compared with that of Baicalin. It can selectively induce apoptosis of the proliferative phase cancer cells, which has scarcely any influence to the normal structure, and it belongs to anticancer drugs of cell cycle inhibitor kind. The product has a rich source of raw materials and has simple process, high purity, low cost, clear metabolic mechanism, high efficiency and low toxicity, which can be made into oral preparations or injections together with acid salts and is expected to become high efficient and low toxicity anti-cancer and AIDS drugs.

  本发明提供了一系列的细胞周期依赖性蛋白激酶（Cdks）抑制剂，即黄芩素类有机胺衍生物，以及它们的合成和使用方法。该制备方法如下：以黄芩根中的黄芩素（或黄芩苷）为引物化合物，按照摩尔比1:1-1.2:1-1.2的比例，将其与甲醛溶液和有机胺化合物混合，加入比黄芩素重量翻倍的甲醇，在50-70℃下反应，过滤沉淀并洗涤，然后干燥，以获得含量不低于97%（重量）的产品。与黄芩苷相比，类似于Flavopiridol和P276-00，黄芩素有机胺衍生物抑制Cdks的活性增加了50倍。它可以选择性地诱导增殖期癌细胞的凋亡，对正常结构几乎没有影响，属于细胞周期抑制剂类的抗癌药物。该产品原材料来源丰富，工艺简单，纯度高，成本低，代谢机制清晰，效率高，毒性低，可以与酸盐一起制成口服制剂或注射剂，预计成为高效低毒的抗癌和艾滋病药物。
• US8377895B2
  申请人：——

  公开号：US8377895B2

  公开（公告）日：2013-02-19
• Design, synthesis, biological evaluation, and molecular docking of novel flavones as H₃R inhibitors
  作者：Gang Wen、Qian Liu、Huabin Hu、Dongmei Wang、Song Wu

  DOI：10.1111/cbdd.12981

  日期：2017.10

  A series of novel flavone derivatives were designed, synthesized, and evaluated for their H3R inhibitory activity. The results showed that four compounds exhibited significant anti-H3R activity. Molecular docking experiments indicated that a salt bridge, hydrogen-bonding, and hydrophobic interactions all contributed to interactions between inhibitors and H3R.

  设计，合成和评估了一系列新颖的黄酮衍生物的H 3 R抑制活性。结果显示四种化合物显示出显着的抗H 3 R活性。分子对接实验表明，盐桥，氢键和疏水相互作用都促进了抑制剂与H 3 R之间的相互作用。