2-isopropylbenzo[d]thiazol-5-ol

• 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-isopropylbenzo[d]thiazol-5-ol
• 英文别名: 2-propan-2-yl-1,3-benzothiazol-5-ol
• 化学式: C₁₀H₁₁NOS
• 分子量: 193.269
• InChiKey: BMUJWDSQGWMXPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-isopropylbenzo[d]thiazol-5-ol 在 potassium carbonate 、 sodium iodide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 12.5h， 生成 5-(4-(4-(2,3-dichlorophenyl)piperidin-1-yl)butoxy)-2-isopropylbenzo[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
• 作为产物：
  描述：

  3-甲氧基异硫氰酸苯酯 在 氢碘酸 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 9.5h， 生成 2-isopropylbenzo[d]thiazol-5-ol
  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

• Substituted imidazole compound and use thereof
  申请人：Kuroita Takanobu

  公开号：US20090227560A1

  公开（公告）日：2009-09-10

  The present invention relates to a compound represented by the formula: wherein each symbol is as defined in the description, or a salt thereof or a prodrug thereof. The compound of the present invention has a superior renin inhibitory activity, and thus is useful as an agent for the prophylaxis or treatment of hypertension, various organ damages attributable to hypertension, and the like.

  本发明涉及一种由以下式表示的化合物：其中每个符号如描述中所定义，或其盐或前药。本发明的化合物具有优越的肾素抑制活性，因此可用作预防或治疗高血压、由高血压引起的各种器官损伤等的药物。
• [EN] SUBSTITUTED IMIDAZOLE COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ D'IMIDAZOLE SUBSTITUÉ ET SON UTILISATION
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2008139941A1

  公开（公告）日：2008-11-20

  [EN] The present invention relates to a compound represented by the formula: wherein each symbol is as defined in the description, or a salt thereof or a prodrug thereof. The compound of the present invention has a superior renin inhibitory activity, and thus is useful as an agent for the prophylaxis or treatment of hypertension, various organ damages attributable to hypertension, and the like.
  [FR] La présente invention concerne un composé représenté par la formule : dans laquelle chaque symbole est tel que défini dans la description, ou l'un de ses sels ou précurseurs. Le composé de la présente invention possède une activité supérieure d'inhibition de la rénine et est ainsi utile en tant qu'agent destiné à la prophylaxie ou au traitement de l'hypertension, de diverses lésions d'organes attribuables à l'hypertension et analogues.
• Discovery of G Protein-Biased D2 Dopamine Receptor Partial Agonists
  作者：Xin Chen、John D. McCorvy、Matthew G. Fischer、Kyle V. Butler、Yudao Shen、Bryan L. Roth、Jian Jin

  DOI：10.1021/acs.jmedchem.6b01208

  日期：2016.12.8

  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.