3-(N-methyl-N-phenylamino)-1-(adenine-9-yl)propane-2-ol | 1310582-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3-(N-methyl-N-phenylamino)-1-(adenine-9-yl)propane-2-ol
• CAS: 1310582-00-3
• 化学式: C₁₅H₁₈N₆O
• 分子量: 298.348
• InChiKey: UXPVLTJFFAFKBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.09
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  N-甲基苯胺 在 potassium carbonate 、 calcium(II) trifluoromethanesulfonate 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 29.0h， 生成 3-(N-methyl-N-phenylamino)-1-(adenine-9-yl)propane-2-ol
  参考文献：
  名称：

  Synthesis, Src kinase inhibitory and anticancer activities of 1-substituted 3-(N-alkyl-N-phenylamino)propane-2-ols

  摘要：

  A series of 3-(N-alkyl-N-phenylamino)propan-2-ol derivatives were synthesized from epichlorohydrine in a multi-step strategy and were evaluated as Src kinase inhibitors. First, epoxy ring opening of epichlorohydrine was carried out in the presence of N-alkylanilines to yield 3-(N-alkyl-N-phenylamino)-1-chloro-propan-2-ol derivatives using Ca(OTf)(2) as catalyst based on our previous studies [1]. Second, ring closure was performed under basic conditions to afford N-epoxymethyl N-alkylaniline derivatives. Finally, the epoxide ring opening with four different secondary amines and three nucleobases afforded the final products, i.e., a series of beta-amino alcohols. All compounds were screened for their inhibitory activity against Src kinase and anticancer activity on human breast carcinoma cells, BT-20 cell line. Among all compounds, 3-N-methyl-N-phenylamino-1-(pyrrolidin-1-yl)propan-2-ol (13b) exhibited the highest inhibitory potency (IC50 = 66.1 mu M) against Src kinase. Structure-activity relationship studies suggested that the incorporation of bulky groups at position I and N-substitution with groups larger than methyl moiety, reduced the inhibitory potency of the compound significantly. Compounds 3-(N-ethyl-N-phenylamino-)-1-(4-methylpiperazin-1-yl)propan-2-ol (14c) and 3-(N-ethyl-N-phenylamino)-1-(thymine-1-yl)propan-2-ol (17) were found to inhibit the growth of breast carcinoma cells by approximately 45-49% at concentration of 50 mu M. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2010.04.022