nordentatin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: nordentatin
• 英文别名: nor-Dentatin；5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)pyrano[3,2-g]chromen-8-one
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: WYMMNGQSPNWCIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  nordentatin 在 甲醇 、 sodium hydroxide 、 Pd-BaSO₄ 、 氢气 、 sodium acetate 、 potassium carbonate 、 potassium iodide 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 19.5h， 生成 黄皮香豆精
  参考文献：
  名称：

  Claisen rearrangements-XIII

  摘要：

  DOI：

  10.1016/s0040-4020(01)82439-x
• 作为产物：
  描述：

  5-羟基邪蒿内酯 在 甲醇 、 sodium acetate 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 44.0h， 生成 nordentatin
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Coumarin Derivatives and Nordentatin

  摘要：

  合成了Nordentatin和10种香豆素衍生物并对其细胞毒性进行了评估。化合物6、7、9和13对NCI-H187细胞系表现出细胞毒性，IC50值在3-7 μg/mL范围内。在合成的香豆素中，化合物4和13对KB细胞系显示出细胞毒性，分别为3.94和6.44 μg/mL的IC50值。幸运的是，由于香豆素4和7对正常细胞表现出微弱的活性或无活性，它们可能成为开发抗癌药物的新型先导化合物之一。

  DOI：

  10.14233/ajchem.2013.13687

文献信息

• COMPOSITIONS AND METHODS FOR TREATMENT OF VIRAL DISEASES
  申请人：Johansen Lisa M.

  公开号：US20100009970A1

  公开（公告）日：2010-01-14

  The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E) and the agent or combination of agents includes sertraline, a sertraline analog, UK-416244, or a UK-416244 analog. Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.

  本发明涉及用于治疗病毒性疾病的组合物、方法和试剂盒。在某些实施方式中，病毒性疾病是由单链RNA病毒、黄病毒科病毒或肝病毒引起的。在特定实施方式中，病毒性疾病是病毒性肝炎（例如甲型肝炎、乙型肝炎、丙型肝炎、丁型肝炎、戊型肝炎），药剂或药剂组合包括舍曲林、舍曲林类似物、UK-416244或UK-416244类似物。还包括用于鉴定可用于治疗病毒性疾病的新化合物的筛选方法。
• New derivatives of a natural nordentatin
  作者：Tin Myo Thant、Nanik Siti Aminah、Alfinda Novi Kristanti、Rico Ramadhan、Hnin Thanda Aung、Yoshiaki Takaya

  DOI：10.1515/chem-2020-0149

  日期：2020.8.3

  Abstract New derivatives were obtained from natural nordentatin (1) previously isolated from the methanol fraction of Clausena excavata by an acylation method. Herein, we report ten new pyranocoumarin derivatives 1a–1j. Their structures were elucidated based on UV-vis, FT-IR, NMR, and DART-MS data. The α-glucosidase inhibition and anticancer activities of nordentatin (1) and its derivatives were also

  摘要 从先前通过酰化方法从 Clausena excavata 的甲醇组分中分离的天然去甲齿素 (1) 中获得了新的衍生物。在此，我们报告了十种新的吡喃香豆素衍生物 1a-1j。基于紫外-可见光、傅里叶变换红外、核磁共振和 DART-MS 数据阐明了它们的结构。还评估了去甲牙本质 (1) 及其衍生物的 α-葡萄糖苷酶抑制和抗癌活性。α-葡萄糖苷酶抑制试验表明衍生物1b、1d、1e、1f、1h、1i和1j对α-葡萄糖苷酶具有较高的抑制活性，IC50值为1.54、9.05、4.87、20.25、12.34、5.2673 mM，而阿卡波糖用作阳性对照，IC50 = 7.57 mM。所有衍生物对宫颈癌 (HeLa) 细胞系均表现出微弱的细胞毒性，IC50 介于 0.25 和 1.25 mM 之间。
• Anti-HBV and cytotoxic activities of pyranocoumarin derivatives
  作者：Chung-Ren Su、Sheau Farn Yeh、Chih Miem Liu、Amooru G. Damu、Tsung-Hsiao Kuo、Po-Cheng Chiang、Kenneth F. Bastow、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmc.2008.12.007

  日期：2009.8

  Four natural pyranocoumarins clausenidin (1), nordentatin (2), clausarin (3), and xanthoxyletin (4) were isolated from the medicinal plant Clausena excavata. Recently, we found that 1 and 2 suppressed hepatitis B virus surface antigen in HepA2 cells, and in addition, 1-3 showed cytotoxic activity against four human cancer cell lines (A549, MCF7, KB, and KB-VIN). To explore the SAR of 1-4, 17 pyranocoumarin analogues (5-21) were designed and synthesized. Among these analogues, 5 and 10 were the most potent against hepatitis B virus with EC50 values of 1.14 and 1.34 mu M, respectively. The most interesting result in the cytotoxicity assay was the significant activity of 1, 5, and 6 against the multi-drug resistant cell line, KB-VIN, without activity against the KB cell line. These data suggest that these three compounds could be useful hits for developing MDR-inverse drugs. (C) 2009 Elsevier Ltd. All rights reserved.
• Efficient syntheses of the coumarins, nordentatin, dentatin and clausarin
  作者：R.D.H. Murray、Z.D. Jorge

  DOI：10.1016/s0040-4039(00)94531-3

  日期：1983.1
• Compositions and methods for treatment of viral diseases
  申请人：Johansen Lisa M.

  公开号：US20080161324A1

  公开（公告）日：2008-07-03

  The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E). Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.