N-methyl-N-(naphthalen-2-ylmethyl)prop-2-yn-1-amine | 56899-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-methyl-N-(naphthalen-2-ylmethyl)prop-2-yn-1-amine
• CAS: 56899-71-9
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: MCLBROSXRZHUFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-甲基炔丙基胺 、 2-溴甲基萘 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 以78%的产率得到N-methyl-N-(naphthalen-2-ylmethyl)prop-2-yn-1-amine
  参考文献：
  名称：

  A fragment-like approach to PYCR1 inhibition

  摘要：

  Pyrroline-5-carboxylate reductase 1 (PYCR1) is the final enzyme involved in the biosynthesis of proline and has been found to be upregulated in various forms of cancer. Due to the role of proline in maintaining the redox balance of cells and preventing apoptosis, PYCR1 is emerging as an attractive oncology target. Previous PYCR1 knockout studies led to a reduction in tumor growth. Accordingly, a small molecule inhibitor of PYCR1 could lead to new treatments for cancer, and a focused screening effort identified pargyline as a fragment-like hit. We report the design and synthesis of the first tool compounds as PYCR1 inhibitors, derived from pargyline, which were assayed to assess their ability to attenuate the production of proline. Structural activity studies have revealed the key determinants of activity, with the most potent compound (4) showing improved activity in vitro in enzyme (IC50 = 8.8 mu M) and pathway relevant effects in cell-based assays.

  DOI：

  10.1016/j.bmcl.2019.07.047