7-chloro-N-(2,6-dimethylphenyl)benzo[d]thiazol-2-amine | 1095537-55-5

• 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: 7-chloro-N-(2,6-dimethylphenyl)benzo[d]thiazol-2-amine
• 英文别名: 7-chloro-N-(2,6-dimethylphenyl)-1,3-benzothiazol-2-amine
• CAS: 1095537-55-5
• 化学式: C₁₅H₁₃ClN₂S
• 分子量: 288.801
• InChiKey: BFLPPSHIERVOKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 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：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(3-chlorophenyl)-3-(2,6-dimethylphenyl)thiourea 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以23%的产率得到7-chloro-N-(2,6-dimethylphenyl)benzo[d]thiazol-2-amine
  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

• Switchable and Scalable Heteroarylation of Primary Amines with 2-Chlorobenzothiazoles under Transition-Metal-Free and Solvent-Free Conditions
  作者：Hua Cheng、Yan-Qiu Zhu、Peng-Fei Liu、Kai-Qiang Yang、Jin Yan、Wei Sang、Xiao-Sheng Tang、Rui Zhang、Cheng Chen

  DOI：10.1021/acs.joc.1c01019

  日期：2021.8.6

  which prevails in versatile natural products and biologically active compounds. Herein, a switchable and scalable C–N coupling protocol was developed for the synthesis of these compounds from 2-chlorobenzothiazoles and primary amines. Gratifyingly, this protocol was achieved under transition-metal-free and solvent-free conditions. Moreover, introducing an appropriate amount of NaH completely switched

  2-氨基苯并噻唑包含一个有价值的结构基序，它普遍存在于多功能天然产物和生物活性化合物中。在此，开发了一种可切换和可扩展的 C-N 偶联方案，用于从 2-氯苯并噻唑和伯胺合成这些化合物。令人欣慰的是，该协议是在无过渡金属和无溶剂条件下实现的。此外，引入适量的 NaH 将选择性从单杂芳基化完全转变为二杂芳基化，进一步的研究为这一新发现提供了基本原理。此外，代表性产物3a和4a 的克级合成通过应用操作简单且无需手套箱的程序来实现，这揭示了这项工作的实际实用性。最后，量化绿色指标的评估提供了证据，证明我们的协议在绿色化学和可持续性方面优于文献。
• Benzothiazoles: Search for anticancer agents
  作者：Malleshappa N. Noolvi、Harun M. Patel、Manpreet Kaur

  DOI：10.1016/j.ejmech.2012.05.028

  日期：2012.8

  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.