N-[2-(3,4-dimethoxyphenyl)ethyl]-1-benzofuran-2-carboxamide | 304889-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-(3,4-dimethoxyphenyl)ethyl]-1-benzofuran-2-carboxamide
• CAS: 304889-22-3
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: ICGLDNFIXLBXNV-UHFFFAOYSA-N

物化性质

• 沸点：
  542.2±45.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯并呋喃-2-羧酸 、 3,4-二甲氧基苯乙胺 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以73%的产率得到N-[2-(3,4-dimethoxyphenyl)ethyl]-1-benzofuran-2-carboxamide
  参考文献：
  名称：

  Identification of benzothiophene amides as potent inhibitors of human nicotinamide phosphoribosyltransferase

  摘要：

  Nicotinamide phosphoribosyltransferase (Nampt) is an attractive therapeutic target for cancer. A Nampt inhibitor with novel benzothiophene scaffold was discovered by high throughput screening. Herein the structure-activity relationship of the benzothiophene Nampt inhibitor was investigated. Several new inhibitors demonstrated potent activity in both biochemical and cell-based assays. In particular, compound 16b showed good Nampt inhibitory activity (IC50 = 0.17 mu M) and in vitro antitumor activity (IC50 = 3.9 mu M, HepG2 cancer cell line). Further investigation indicated that compound 16b could efficiently induce cancer cell apoptosis. Our findings provided a good starting point for the discovery of novel antitumor agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.101

文献信息

• MODULATORS OF ATP-BINDING CASSETTE TRANSPORTERS
  申请人：Hadida-Ruah Sara S.

  公开号：US20120035179A1

  公开（公告）日：2012-02-09

  The present invention provides compounds of Formula I useful as modulators of ABC transporter activity, or a pharmaceutically acceptable salt thereof, wherein R B , n, B, R C , R D , R E , A, and Z are described generally and in classes and subclasses below. The present invention also provides pharmaceutical compositions, methods and kits associated with Formula I, useful for as modulators, and for the treatments of disease and disease conditions associated with ABC transporter proteins.

  本发明提供了I式化合物，其作为ABC转运蛋白活性调节剂或其药学上可接受的盐有用，其中RB、n、B、RC、RD、RE、A和Z通常在以下类别和子类别中描述。本发明还提供了与I式相关的制药组合物、方法和工具包，有用于调节剂和用于治疗与ABC转运蛋白相关的疾病和疾病条件。
• Modulators of ATP-Binding Cassette Transporters
  申请人：Hadida Ruah Sara S.

  公开号：US20100125090A1

  公开（公告）日：2010-05-20

  The present invention provides compounds of Formula I useful as modulators of ABC transporter activity, or a pharmaceutically acceptable salt thereof, wherein R B , n, B, R C , R D , R E , A, and Z are described generally and in classes and subclasses below. The present invention also provides pharmaceutical compositions, methods and kits associated with Formula I, useful for as modulators, and for the treatments of disease and disease conditions associated with ABC transporter proteins.

  本发明提供了公式I的化合物，它们可用作ABC转运蛋白活性调节剂或其药学上可接受的盐，其中RB、n、B、RC、RD、RE、A和Z通常和在下面的类和亚类中描述。本发明还提供了与公式I相关的制药组合物、方法和工具包，可用于作为调节剂，并用于治疗与ABC转运蛋白相关的疾病和疾病状况。
• US7598412B2
  申请人：——

  公开号：US7598412B2

  公开（公告）日：2009-10-06
• Identification of benzothiophene amides as potent inhibitors of human nicotinamide phosphoribosyltransferase
  作者：Wei Chen、Guoqiang Dong、Shipeng He、Tianying Xu、Xia Wang、Na Liu、Wannian Zhang、Chaoyu Miao、Chunquan Sheng

  DOI：10.1016/j.bmcl.2015.12.101

  日期：2016.2

  Nicotinamide phosphoribosyltransferase (Nampt) is an attractive therapeutic target for cancer. A Nampt inhibitor with novel benzothiophene scaffold was discovered by high throughput screening. Herein the structure-activity relationship of the benzothiophene Nampt inhibitor was investigated. Several new inhibitors demonstrated potent activity in both biochemical and cell-based assays. In particular, compound 16b showed good Nampt inhibitory activity (IC50 = 0.17 mu M) and in vitro antitumor activity (IC50 = 3.9 mu M, HepG2 cancer cell line). Further investigation indicated that compound 16b could efficiently induce cancer cell apoptosis. Our findings provided a good starting point for the discovery of novel antitumor agents. (C) 2015 Elsevier Ltd. All rights reserved.