5-methoxy-2-(trifluoromethyl)benzo[d]thiazole | 1188161-13-8

• 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: 5-methoxy-2-(trifluoromethyl)benzo[d]thiazole
• 英文别名: 5-methoxy-2-(trifluoromethyl)-1,3-benzothiazole
• CAS: 1188161-13-8
• 化学式: C₉H₆F₃NOS
• 分子量: 233.214
• InChiKey: BGOKLMKAZCEVDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-(trifluoromethyl)benzo[d]thiazole 在 氢碘酸 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  Discovery of G Protein-Biased D2 Dopamine Receptor Partial Agonists

  摘要：

  Biased ligands (also known as functionally selective ligands) of G protein-coupled receptors are valuable tools for dissecting the roles of G protein-dependent and independent signaling pathways in health and disease. Biased ligands have also been increasingly pursued by the biomedical community as promising therapeutics with improved efficacy and reduced side effects compared with unbiased ligands. We previously discovered first-in-class,beta-arrestin-biased agonists of dopamine D2 receptor (D2R) by extensively exploring multiple regions of aripiprazole, a balanced D2R agonist. In our continuing efforts to identify biased agonists of D2R, we unexpectedly discovered a G protein-biased agonist of D2R, compound 1, which is the first G protein-biased D2R agonist from the aripiprazole scaffold. We designed and synthesized novel analogues to explore two regions of 1 and conducted structure functional selectivity relationship (SFSR) studies. Here we report the discovery of 1, findings from our SFSR studies, and characterization of novel G protein-biased D2R agonists.

  DOI：

  10.1021/acs.jmedchem.6b01208
• 作为产物：
  描述：

  Ethanimidoyl chloride, 2,2,2-trifluoro-N-(3-methoxyphenyl)- 在 palladium dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 3.5h， 以85%的产率得到5-methoxy-2-(trifluoromethyl)benzo[d]thiazole
  参考文献：
  名称：

  Discovery of G Protein-Biased D2 Dopamine Receptor Partial Agonists

  摘要：

  Biased ligands (also known as functionally selective ligands) of G protein-coupled receptors are valuable tools for dissecting the roles of G protein-dependent and independent signaling pathways in health and disease. Biased ligands have also been increasingly pursued by the biomedical community as promising therapeutics with improved efficacy and reduced side effects compared with unbiased ligands. We previously discovered first-in-class,beta-arrestin-biased agonists of dopamine D2 receptor (D2R) by extensively exploring multiple regions of aripiprazole, a balanced D2R agonist. In our continuing efforts to identify biased agonists of D2R, we unexpectedly discovered a G protein-biased agonist of D2R, compound 1, which is the first G protein-biased D2R agonist from the aripiprazole scaffold. We designed and synthesized novel analogues to explore two regions of 1 and conducted structure functional selectivity relationship (SFSR) studies. Here we report the discovery of 1, findings from our SFSR studies, and characterization of novel G protein-biased D2R agonists.

  DOI：

  10.1021/acs.jmedchem.6b01208

文献信息

• One–Pot Assembly of 2‐Trifluoromethyl Benzothiazole and Benzoselenazole via Copper–Mediated Three–Component Cascade Reaction
  作者：Yangjie Huang、Chenhui You、Biqiong Hong、Xiaoyan Han、Zhiqiang Weng

  DOI：10.1002/asia.202400331

  日期：2024.7.2

  A domino one–pot synthesis of 2-(trifluoromethyl) benzothiazole via copper–mediated three–component cascade reaction starting from the easily accessible starting materials such as o-iodoanilines, methyl trifluoropyruvate, and elemental sulfur is reported. The present strategy displayed a comprehensive substrate scope and good functional group tolerance and enabled access to a variety of substituted

  据报道，从邻碘苯胺、三氟丙酮酸甲酯和元素硫等容易获得的起始原料开始，通过铜介导的三组分级联反应，多米诺一锅合成2-(三氟甲基)苯并噻唑。本策略显示了全面的底物范围和良好的官能团耐受性，并且能够获得多种取代的2-(三氟甲基)苯并噻唑。还利用该反应方法合成了 2-(三氟甲基)苯并硒唑。
• A General and Straightforward Method for the Synthesis of 2-Trifluoromethylbenzothiazoles
  作者：Jiangtao Zhu、Zixian Chen、Haibo Xie、Shan Li、Yongming Wu

  DOI：10.1021/ol1006899

  日期：2010.5.21

  An efficient one-pot method for the synthesis of 2-trifluoromethylbenzothiazoles by the treatment of trifluoromethylimidoyl chlorides with sodium hydrosulfide hydrate using PdCl(2) as the sole catalyst in DMSO is described. The reaction proceeds via thiolation/C H bond functionalization/C S bond formation in moderate to high yields with good functional group tolerance.