N-(3-(1H-imidazol-1-yl)propyl)benzofuran-2-carboxamide | 95059-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: N-(3-(1H-imidazol-1-yl)propyl)benzofuran-2-carboxamide
• 英文别名: Benzofuran-2-carboxylic acid (3-imidazol-1-yl-propyl)-amide；N-(3-imidazol-1-ylpropyl)-1-benzofuran-2-carboxamide
• CAS: 95059-48-6
• 化学式: C₁₅H₁₅N₃O₂
• 分子量: 269.303
• InChiKey: HPZOOQXHLMXNNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  60.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(3-氨基丙基)咪唑 、 苯并呋喃-2-羧酸 在 水 、 N,N'-羰基二咪唑 作用下， 生成 N-(3-(1H-imidazol-1-yl)propyl)benzofuran-2-carboxamide
  参考文献：
  名称：

  Thromboxane synthetase inhibitors and antihypertensive agents. 3. N-[(1H-imidazol-1-yl)alkyl]heteroaryl amides as potent enzyme inhibitors

  摘要：

  The title compounds were prepared as the heterocyclic analogues of thromboxane (TX) synthetase inhibitors and antihypertensive agents previously reported from our laboratories. These compounds were at least as active TX synthetase inhibitors as their benzene isosteres with the indole derivatives 50-55 having the most potent enzyme inhibiting activity measured to date in our laboratories. The best compound, 54, is more than 200-fold more potent than the standard, dazoxiben. In contrast, the antihypertensive activity of these series of compounds was no better than their benzene counterparts and is far lower than the isoindoledione derivatives prepared in a related series. The structure-activity relationship results from this study were similar to our previous observations and include the fact that the amide moiety effectively replaces a carboxylic acid for potent TX synthetase inhibition and that a four to six methylene unit separation (approximately 8.5 A) between amide and imidazole moieties achieves maximal activity.

  DOI：

  10.1021/jm00389a013

文献信息

• Thromboxane synthetase inhibitors and antihypertensive agents. 3. N-[(1H-imidazol-1-yl)alkyl]heteroaryl amides as potent enzyme inhibitors
  作者：Jeffery B. Press、William B. Wright、Peter S. Chan、Margie F. Haug、Joseph W. Marsico、Andrew S. Tomcufcik

  DOI：10.1021/jm00389a013

  日期：1987.6

  The title compounds were prepared as the heterocyclic analogues of thromboxane (TX) synthetase inhibitors and antihypertensive agents previously reported from our laboratories. These compounds were at least as active TX synthetase inhibitors as their benzene isosteres with the indole derivatives 50-55 having the most potent enzyme inhibiting activity measured to date in our laboratories. The best compound, 54, is more than 200-fold more potent than the standard, dazoxiben. In contrast, the antihypertensive activity of these series of compounds was no better than their benzene counterparts and is far lower than the isoindoledione derivatives prepared in a related series. The structure-activity relationship results from this study were similar to our previous observations and include the fact that the amide moiety effectively replaces a carboxylic acid for potent TX synthetase inhibition and that a four to six methylene unit separation (approximately 8.5 A) between amide and imidazole moieties achieves maximal activity.
• 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.