trans-N-(4-(2-(((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)cyclohexyl)benzofuran-2-carboxamide | 1062467-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: trans-N-(4-(2-(((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)cyclohexyl)benzofuran-2-carboxamide
• CAS: 1062467-98-4
• 化学式: C₂₇H₃₆N₄O₂S
• 分子量: 480.674
• InChiKey: WTWMPEGOAVNGOY-JBACZVJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  84.39
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  苯并呋喃-2-羧酸 、 (6S)-N⁶-[2-(trans-4-Aminocyclohexyl)ethyl]-N⁶-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以60 mg的产率得到trans-N-(4-(2-(((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)cyclohexyl)benzofuran-2-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Potent and Selective Ligands for the Dopamine 3 (D₃) Receptor with a Novel in Vivo Behavioral Profile

  摘要：

  A series of compounds structurally related to pramipexole were designed, synthesized, and evaluated as ligands for the dopamine 3 (D-3) receptor. Compound 12 has a K-i value of 0.41 nM to D3 and a selectivity of > 30000- and 800-fold over the D-1-like and D-2 receptors, respectively. Our in vivo functional assays showed that this compound is a partial agonist at the D-3 receptor with no detectable activity at the D-2 receptor.

  DOI：

  10.1021/jm800471h

文献信息

• Selective Ligands for the Dopamine 3 (D3) Receptor and Methods of using the Same
  申请人：Wang Shaomeng

  公开号：US20110184033A1

  公开（公告）日：2011-07-28

  Potent and selective ligands for the dopamine 3 (D 3 ) receptor are disclosed. The D3 receptor ligands have a structural formula (I) wherein X is C═O or SO 2 , R 1 is C 1-6 alkyl, R 2 is aryl, heteroaryl, aryl, —(CH 2 ) 1-3 aryl, or —(CH 2 ) 1-3 heteroaryl, and n is 0 or 1. Methods of using the D 3 receptor ligands in the treatment of diseases and conditions wherein modulation of the D 3 receptor provides a benefit also are disclosed.

  揭示了对多巴胺3（D3）受体具有强效和选择性的配体。D3受体配体具有结构式（I），其中X是C═O或SO2，R1是C1-6烷基，R2是芳基，杂环芳基，芳基，—（CH2）1-3芳基或—（CH2）1-3杂环芳基，n为0或1。还揭示了在调节D3受体提供益处的疾病和病况的治疗中使用D3受体配体的方法。
• Selective ligands for the dopamine 3 (D3) receptor and methods of using the same
  申请人：The Regents of the University of Michigan

  公开号：US08283368B2

  公开（公告）日：2012-10-09

  Potent and selective ligands for the dopamine 3 (D3) receptor are disclosed. The D3 receptor ligands have a structural formula (I) wherein X is C═O or SO2, R1 is C1-6 alkyl, R2 is aryl, heteroaryl, aryl, —(CH2)1-3aryl, or —(CH2)1-3heteroaryl, and n is 0 or 1. Methods of using the D3 receptor ligands in the treatment of diseases and conditions wherein modulation of the D3 receptor provides a benefit also are disclosed.

  公开了用于多巴胺3（D3）受体的有效和选择性配体。D3受体配体具有结构式（I），其中X为C═O或SO2，R1为C1-6烷基，R2为芳基，杂环芳基，芳基，—（CH2）1-3芳基或—（CH2）1-3杂环芳基，n为0或1。还公开了使用D3受体配体治疗调节D3受体可提供益处的疾病和状况的方法。
• US8283368B2
  申请人：——

  公开号：US8283368B2

  公开（公告）日：2012-10-09
• Design, Synthesis, and Evaluation of Potent and Selective Ligands for the Dopamine 3 (D₃) Receptor with a Novel in Vivo Behavioral Profile
  作者：Jianyong Chen、Gregory T. Collins、Jian Zhang、Chao-Yie Yang、Beth Levant、James Woods、Shaomeng Wang

  DOI：10.1021/jm800471h

  日期：2008.10.9

  A series of compounds structurally related to pramipexole were designed, synthesized, and evaluated as ligands for the dopamine 3 (D-3) receptor. Compound 12 has a K-i value of 0.41 nM to D3 and a selectivity of > 30000- and 800-fold over the D-1-like and D-2 receptors, respectively. Our in vivo functional assays showed that this compound is a partial agonist at the D-3 receptor with no detectable activity at the D-2 receptor.