5-dimethylamino-3-phenylisoquinolin-1(2H)-one | 203628-13-1

• 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-phenylisoquinolin-1(2H)-one
• 英文别名: 5-(dimethylamino)-3-phenyl-2H-isoquinolin-1-one
• CAS: 203628-13-1
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: LXSXPQLKZHVWQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-phenylisoquinolin-1(2H)-one 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 N,N-dimethyl-1-(4-methylpiperazin-1-yl)-3-phenylisoquinolin-5-amine
  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：

  苯甲腈 、 3-dimethylamino-2-methyl-N,N-dimethylbenzamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以62%的产率得到5-dimethylamino-3-phenylisoquinolin-1(2H)-one
  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

文献信息

• Development of 3-aryl-1-isoquinolinamines as potent antitumor agents based on CoMFA
  作者：Su Hui Yang、Hue Thi My Van、Thanh Nguyen Le、Daulat Bikram Khadka、Suk Hee Cho、Kyung-Tae Lee、Eung-Seok Lee、Young Bok Lee、Chang-Ho Ahn、Won-Jea Cho

  DOI：10.1016/j.ejmech.2010.08.042

  日期：2010.11

  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.
• Synthesis and biological evaluation of 3-arylisoquinolines as antitumor agents
  作者：Won-Jea Cho、Myun-Ji Park、Byung-Ho Chung、Chong-Ok Lee

  DOI：10.1016/s0960-894x(97)10190-1

  日期：1998.1

  To investigate the structure-activity relationship of 7,8-dimethoxy-2-methyl-3-(4,5-methylenedioxy-2-vinylphenyl)isoquinolin-1(2H)-one 2, diverse substituted 3-arylisoquinolines were synthesized and tested in vitro antitumor activity against five human tumor cell lines. The results showed a broad antitumor spectrum for a series of 3-arylisoquinolines. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Synthesis and comparative molecular field analysis (CoMFA) of antitumor 3-arylisoquinoline derivatives
  作者：Won-Jea Cho、Eui-Ki Kim、Myun-Ji Park、Sang-Un Choi、Chong-Ock Lee、Seung Hoon Cheon、Bo-Gil Choi、Byung-Ho Chung

  DOI：10.1016/s0968-0896(98)80019-9

  日期：1998.12

  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.