2-(N-2,6-dimethylphenyl)amino-7-nitrobenzothiazole | 820101-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(N-2,6-dimethylphenyl)amino-7-nitrobenzothiazole
• 英文别名: N-(2,6-dimethylphenyl)-7-nitrobenzo[d]thiazol-2-amine；N-(2,6-Dimethylphenyl)-7-nitro-1,3-benzothiazol-2-amine；N-(2,6-dimethylphenyl)-7-nitro-1,3-benzothiazol-2-amine
• CAS: 820101-42-6
• 化学式: C₁₅H₁₃N₃O₂S
• 分子量: 299.353
• InChiKey: LZNQVELWYQXSSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  99
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-硝基异硫氰酸苯酯 在 溴 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.0h， 生成 2-(N-2,6-dimethylphenyl)amino-7-nitrobenzothiazole
  参考文献：
  名称：

  Benzothiazoles: Search for anticancer agents

  摘要：

  Novel derivatives of 2-amino benzothiazoles 4(a-j) have been synthesized and tested for their antitumor activity using National Cancer Institute (NCI) disease oriented antitumor screen protocol against nine panel of cancer cell lines. Among the synthesized compounds, two compounds were granted NSC code and screened at National Cancer Institute (NCI)-USA for anticancer activity at a single high dose (10(-5) M) and five dose in full NCI 60 cell panel. Among the selected compounds,7-chloro-N-(2,6-dichlorophenyl) benzo[d]thiazol-2-amine (4i) with GI(50) values of 7.18 x 10(-8) M against Non-Small Cell HOP-92 Lung Cancer cell line proved to be the most active members in this study. Virtual screening was carried out through docking the designed compounds into the ATP binding site of epidermal growth factor receptor (EGFR) to predict if these compounds have analogous binding mode to the EGFR inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.028

文献信息

• Synthesis of 2-N-alkyl(aryl)amino-7-nitrobenzothiazoles
  作者：Shenlin Huang、Peter J. Connolly

  DOI：10.1016/j.tetlet.2004.10.117

  日期：2004.12

  A highly efficient synthesis of 2-N-alkyl(aryl)amino-7-nitrobenzothiazoles has been developed. The key step involves intramolecular cyclization of a thiourea facilitated by the nitro group. (C) 2004 Elsevier Ltd. All rights reserved.