2-amino-N-(3,4-dimethoxyphenethyl)acetamide hydrochloride | 189753-05-7

• 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: 2-amino-N-(3,4-dimethoxyphenethyl)acetamide hydrochloride
• 英文别名: 2-amino-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide
• CAS: 189753-05-7
• 化学式: C₁₂H₁₈N₂O₃
• mdl: MFCD09724234
• 分子量: 238.287
• InChiKey: ZUNGDIJOAINYJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲基噻吩-2-羧酸 、 2-amino-N-(3,4-dimethoxyphenethyl)acetamide hydrochloride 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以0.24 g的产率得到N-(2-((3,4-dimethoxyphenethyl)amino)-2-oxoethyl)-3-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
• 作为产物：
  描述：

  Carbamic acid, [2-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-2-oxoethyl]-, 1,1-dimethylethyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-amino-N-(3,4-dimethoxyphenethyl)acetamide hydrochloride
  参考文献：
  名称：

  新型L-氨基酸基镇痛药的合成及生物活性

  摘要：

  描述了一系列基于L-氨基酸的化合物的合成和镇痛活性。这些化合物被设计为潜在的N型钙通道阻滞剂，其结构通过1H NMR和ESI-MS光谱确认。某些化合物在Mouse Hot-Plate测试中显示出明显的镇痛活性。根据药理实验数据，我们进行了初步的结构活性研究，结果表明这种化合物可用于开发新的止痛药。

  DOI：

  10.2174/157018010791163497

文献信息

• Synthesis and Biological Activity of Novel L-Amino Acid Based Analgesic Compounds
  作者：Junzhu Pan、Qianqian Wang、Gu He、Liang Ouyang、Li Guo

  DOI：10.2174/157018010791163497

  日期：2010.6.1

  Synthesis and analgesic activity studies of a series of L-amino acid based compounds were described. These compounds were designed as potential N-type Calcium Channel Blockers and their structures were confirmed by 1H NMR and ESI-MS spectra. Some of the compounds exhibited significant analgesic activity in Mouse Hot-Plate tests. According to the data of pharmacological experiments, we carried out preliminary

  描述了一系列基于L-氨基酸的化合物的合成和镇痛活性。这些化合物被设计为潜在的N型钙通道阻滞剂，其结构通过1H NMR和ESI-MS光谱确认。某些化合物在Mouse Hot-Plate测试中显示出明显的镇痛活性。根据药理实验数据，我们进行了初步的结构活性研究，结果表明这种化合物可用于开发新的止痛药。
• Sulfur incorporation generally improves Ricin inhibition in pterin-appended glycine-phenylalanine dipeptide mimics
  作者：Paul A. Wiget、Lawrence A. Manzano、Jeff M. Pruet、Grace Gao、Ryota Saito、Arthur F. Monzingo、Karl R. Jasheway、Jon D. Robertus、Eric V. Anslyn

  DOI：10.1016/j.bmcl.2013.10.017

  日期：2013.12

  Several 7-aminoamido-pterins were synthesized to evaluate the electronic and biochemical subtleties observed in the 'linker space' when N-N-(pterin-7-yl)carbonylglycyl}-l-phenylalanine 1 was bound to the active site of RTA. The gylcine-phenylalanine dipeptide analogs included both amides and thioamides. Decarboxy gly-phe analog 2 showed a 6.4-fold decrease in potency (IC50 = 128 μM), yet the analogous thioamide 7 recovered the lost activity and performed similarly to the parent inhibitor (IC50 = 29 μM). Thiourea 12 exhibited an IC50 nearly six times lower than the oxo analog 13. All inhibitors showed the pterin head-group firmly bound in their X-ray structures yet the pendants were not fully resolved suggesting that all pendants are not firmly bound in the RTA linker space. Calculated log P values do not correlate to the increase in bioactivity suggesting other factors dominate.
• 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.