N-(2-((3,4-dimethoxyphenethyl)amino)-2-oxoethyl)-5-methylthiophene-2-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-((3,4-dimethoxyphenethyl)amino)-2-oxoethyl)-5-methylthiophene-2-carboxamide
• 英文别名: N-[2-(3,4-dimethoxyphenyl)ethyl]-2-[(5-methylthiophen-2-yl)formamido]acetamide；N-[2-[2-(3,4-dimethoxyphenyl)ethylamino]-2-oxoethyl]-5-methylthiophene-2-carboxamide
• 化学式: C₁₈H₂₂N₂O₄S
• 分子量: 362.45
• InChiKey: IZENEEXKHSGBIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-(2-((3,4-dimethoxyphenethyl)amino)-2-oxoethyl)-5-methylthiophene-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

• 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.