N-[1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethyl]-3-phenylpropan-1-amine | 1454618-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-[1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethyl]-3-phenylpropan-1-amine
• 英文别名: N-[1-(7-methoxy-2,2-dimethyl-chromen-6-yl)ethyl]-3-phenyl-propan-1-amine；N-[1-(7-methoxy-2,2-dimethylchromen-6-yl)ethyl]-3-phenylpropan-1-amine
• CAS: 1454618-07-5
• 化学式: C₂₃H₂₉NO₂
• 分子量: 351.489
• InChiKey: XGJMHBHRVKZMEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-[1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethyl]-3-phenylpropan-1-amine 在 ammonium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.25h， 以47%的产率得到N-[1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethyl]-N-methyl-3-phenylpropan-1-amine
  参考文献：
  名称：

  Natural Product Derived Antiprotozoal Agents: Synthesis, Biological Evaluation, and Structure–Activity Relationships of Novel Chromene and Chromane Derivatives

  摘要：

  Various natural products with the chromane and chromene scaffold exhibit high antiprotozoal activity. The natural product encecalin (7) served as key intermediate for the synthesis of different ethers 9, amides 11, and amines 12. The chromane analogues 14 and the phenols 15 were obtained by reductive amination of ketones 13 and 6, respectively. Angelate 3, ethers 9, and amides 11 did not show considerable antiprotozoal activity. However, the chromene and chromane derived amines 12, 14, and 15 revealed promising antiprotozoal activity and represent novel lead compounds. Whereas benzylamine 12a and a-methylbenzylamine 12g were active against P. falciparum with IC50 values in the range of chloroquine, the analogous phenols 15a and 15b were unexpectedly 10- to 25-fold more potent than chloroquine with selectivity indexes of 6760 and 1818, respectively. The phenylbutylamine 14d based on the chromane scaffold has promising activity against T. brucei rhodesiense and L. donovani.

  DOI：

  10.1021/jm401007p
• 作为产物：
  描述：

  7-羟基-2,2-二甲基苯并二氢吡喃 在 aluminum (III) chloride 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.17h， 生成 N-[1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethyl]-3-phenylpropan-1-amine
  参考文献：
  名称：

  Natural Product Derived Antiprotozoal Agents: Synthesis, Biological Evaluation, and Structure–Activity Relationships of Novel Chromene and Chromane Derivatives

  摘要：

  Various natural products with the chromane and chromene scaffold exhibit high antiprotozoal activity. The natural product encecalin (7) served as key intermediate for the synthesis of different ethers 9, amides 11, and amines 12. The chromane analogues 14 and the phenols 15 were obtained by reductive amination of ketones 13 and 6, respectively. Angelate 3, ethers 9, and amides 11 did not show considerable antiprotozoal activity. However, the chromene and chromane derived amines 12, 14, and 15 revealed promising antiprotozoal activity and represent novel lead compounds. Whereas benzylamine 12a and a-methylbenzylamine 12g were active against P. falciparum with IC50 values in the range of chloroquine, the analogous phenols 15a and 15b were unexpectedly 10- to 25-fold more potent than chloroquine with selectivity indexes of 6760 and 1818, respectively. The phenylbutylamine 14d based on the chromane scaffold has promising activity against T. brucei rhodesiense and L. donovani.

  DOI：

  10.1021/jm401007p

文献信息

• Natural Product Derived Antiprotozoal Agents: Synthesis, Biological Evaluation, and Structure–Activity Relationships of Novel Chromene and Chromane Derivatives
  作者：Dipak Harel、Dirk Schepmann、Helge Prinz、Reto Brun、Thomas J. Schmidt、Bernhard Wünsch

  DOI：10.1021/jm401007p

  日期：2013.9.26

  Various natural products with the chromane and chromene scaffold exhibit high antiprotozoal activity. The natural product encecalin (7) served as key intermediate for the synthesis of different ethers 9, amides 11, and amines 12. The chromane analogues 14 and the phenols 15 were obtained by reductive amination of ketones 13 and 6, respectively. Angelate 3, ethers 9, and amides 11 did not show considerable antiprotozoal activity. However, the chromene and chromane derived amines 12, 14, and 15 revealed promising antiprotozoal activity and represent novel lead compounds. Whereas benzylamine 12a and a-methylbenzylamine 12g were active against P. falciparum with IC50 values in the range of chloroquine, the analogous phenols 15a and 15b were unexpectedly 10- to 25-fold more potent than chloroquine with selectivity indexes of 6760 and 1818, respectively. The phenylbutylamine 14d based on the chromane scaffold has promising activity against T. brucei rhodesiense and L. donovani.