3-phenylisoquinolin-1(2H)-thione

• 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: 3-phenylisoquinolin-1(2H)-thione
• 英文别名: 3-phenylisoquinoline-1(2H)-thione；3-Phenyl isoquinoline-1(2h)-thione；3-phenyl-2H-isoquinoline-1-thione
• 化学式: C₁₅H₁₁NS
• 分子量: 237.325
• InChiKey: HRVNMEXUWJHJCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-溴-4'-氰基苯乙酮 、 3-phenylisoquinolin-1(2H)-thione 以 乙醇 为溶剂， 反应 2.0h， 以79%的产率得到4-(2-(3-phenylisoquinolin-1-ylthio)acetyl)benzonitrile
  参考文献：
  名称：

  Synthesis of Diversified Thioethers, 1-Aroylalkylisoquinolin-1-yl Thioethers, by Electrophilic S-Alkylation of 3-Phenyl Isoquinoline-1(2H)-thione

  摘要：

  A mild and efficient method for the synthesis of thioethers has been developed. The 3-phenylisoquinoline-1(2H)-thione underwent S-alkylation to afford structurally diverse sulfides in high yield.

  DOI：

  10.1080/10426500903383945
• 作为产物：
  描述：

  N,N,2-三甲基-苯甲酰胺 在 劳森试剂 、 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 生成 3-phenylisoquinolin-1(2H)-thione
  参考文献：
  名称：

  Synthesis and biological evaluation of 3-arylisoquinolines as antitumor agents

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(97)10190-1

文献信息

• 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.
• Synthesis of Diversified Thioethers, 1-Aroylalkylisoquinolin-1-yl Thioethers, by Electrophilic S-Alkylation of 3-Phenyl Isoquinoline-1(2H)-thione
  作者：P. Manivel、F. Nawaz Khan、Venkatesha R. Hatwar

  DOI：10.1080/10426500903383945

  日期：2010.8.25

  A mild and efficient method for the synthesis of thioethers has been developed. The 3-phenylisoquinoline-1(2H)-thione underwent S-alkylation to afford structurally diverse sulfides in high yield.
• 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.