5-dimethylamino-3-(2-methylphenyl)isoquinolin-1(2H)-one | 220630-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-dimethylamino-3-(2-methylphenyl)isoquinolin-1(2H)-one
• 英文别名: 5-(dimethylamino)-3-(2-methylphenyl)-2H-isoquinolin-1-one
• CAS: 220630-90-0
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: CBSTWKIQVBICNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-dimethylamino-3-(2-methylphenyl)isoquinolin-1(2H)-one 在 三氯氧磷 作用下， 以84%的产率得到1-chloro-5-dimethylamino-3-(2-methylphenyl)isoquinoline
  参考文献：
  名称：

  Synthesis and comparative molecular field analysis (CoMFA) of antitumor 3-arylisoquinoline derivatives

  摘要：

  In this study a series of 3-arylisoquinoline derivatives were synthesized and cytotoxicity against human melanoma tumor cell evaluated, and a three dimensional quantitative structure-activity relationship was investigated using the comparative molecular field analysis (CoMFA). The results suggested that the electrostatic, steric and hydrophobic factors of 3-arylisoquinolines were strongly correlated with the antitumor activity. Considerable predictive ability (cross-validated r(2) as high as 0.721) was obtained through CoMFA, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)80019-9
• 作为产物：
  描述：

  邻甲基苯腈 、 N,N-diethyl-3-(dimethylamino)-2-methylbenzamide 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 5-dimethylamino-3-(2-methylphenyl)isoquinolin-1(2H)-one
  参考文献：
  名称：

  Development of 3-aryl-1-isoquinolinamines as potent antitumor agents based on CoMFA

  摘要：

  Various substituted 3-aryl-1-isoquinolinamines were designed and synthesized based on the previously constructed CoMFA model. Most of the synthesized compounds showed excellent potency in eight different human tumor cell lines as expected. In order to find the exact cytotoxic mechanism of these 3-aryl-1-isoquinolinamines, we analyzed the cell cycle dynamics by flow cytometry and found that 3-aryl-1-isoquinolinamine 6k-treated HeLa cells were arrested in G2/M phase, which is related to apoptosis. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.042