(S)-4-(5-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)pentyl)-2-methoxyphenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-4-(5-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)pentyl)-2-methoxyphenol
• 英文别名: 4-[5-[[(6S)-2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl]-propylamino]pentyl]-2-methoxyphenol
• 化学式: C₂₂H₃₃N₃O₂S
• 分子量: 403.589
• InChiKey: PXPHOMJZPNVWMG-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  99.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-(5-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)pentyl)-2-methoxyphenol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以71%的产率得到(S)-4-(5-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)pentyl)benzene-1,2-diol
  参考文献：
  名称：

  Novel multifunctional dopamine D 2 /D 3 receptors agonists with potential neuroprotection and anti-alpha synuclein protein aggregation properties

  摘要：

  Our ongoing drug development endeavor to design compounds for symptomatic and neuroprotective treatment of Parkinson's disease (PD) led us to carry out a structure activity relationship study based on dopamine agonists pramipexole and 5-OHDPAT. Our goal was to incorporate structural elements in these agonists in a way to preserve their agonist activity while producing inhibitory activity against aggregation of alpha-synuclein protein. In our design we appended various catechol and related phenol derivatives to the parent agonists via different linker lengths. Structural optimization led to development of several potent agonists among which (-)-8a, (-)-14 and (-)-20 exhibited potent neuroprotective properties in a cellular PD model involving neurotoxin 6-OHDA. The lead compounds (-)-8a and (-)-14 were able to modulate aggregation of alpha-synuclein protein efficiently. Finally, in an in vivo PD animal model, compound (-)-8a exhibited efficacious anti-parkinsonian effect. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.021
• 作为产物：
  描述：

  (Z)-ethyl 5-(4-hydroxy-3-methoxyphenyl)pent-4-enoate 在 palladium 10% on activated carbon 、 氢气 、 二异丁基氢化铝 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 41.0h， 生成 (S)-4-(5-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)pentyl)-2-methoxyphenol
  参考文献：
  名称：

  Novel multifunctional dopamine D 2 /D 3 receptors agonists with potential neuroprotection and anti-alpha synuclein protein aggregation properties

  摘要：

  Our ongoing drug development endeavor to design compounds for symptomatic and neuroprotective treatment of Parkinson's disease (PD) led us to carry out a structure activity relationship study based on dopamine agonists pramipexole and 5-OHDPAT. Our goal was to incorporate structural elements in these agonists in a way to preserve their agonist activity while producing inhibitory activity against aggregation of alpha-synuclein protein. In our design we appended various catechol and related phenol derivatives to the parent agonists via different linker lengths. Structural optimization led to development of several potent agonists among which (-)-8a, (-)-14 and (-)-20 exhibited potent neuroprotective properties in a cellular PD model involving neurotoxin 6-OHDA. The lead compounds (-)-8a and (-)-14 were able to modulate aggregation of alpha-synuclein protein efficiently. Finally, in an in vivo PD animal model, compound (-)-8a exhibited efficacious anti-parkinsonian effect. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.021

文献信息

• Novel multifunctional dopamine D 2 /D 3 receptors agonists with potential neuroprotection and anti-alpha synuclein protein aggregation properties
  作者：Dan Luo、Horrick Sharma、Deepthi Yedlapudi、Tamara Antonio、Maarten E.A. Reith、Aloke K. Dutta

  DOI：10.1016/j.bmc.2016.08.021

  日期：2016.11

  Our ongoing drug development endeavor to design compounds for symptomatic and neuroprotective treatment of Parkinson's disease (PD) led us to carry out a structure activity relationship study based on dopamine agonists pramipexole and 5-OHDPAT. Our goal was to incorporate structural elements in these agonists in a way to preserve their agonist activity while producing inhibitory activity against aggregation of alpha-synuclein protein. In our design we appended various catechol and related phenol derivatives to the parent agonists via different linker lengths. Structural optimization led to development of several potent agonists among which (-)-8a, (-)-14 and (-)-20 exhibited potent neuroprotective properties in a cellular PD model involving neurotoxin 6-OHDA. The lead compounds (-)-8a and (-)-14 were able to modulate aggregation of alpha-synuclein protein efficiently. Finally, in an in vivo PD animal model, compound (-)-8a exhibited efficacious anti-parkinsonian effect. (C) 2016 Elsevier Ltd. All rights reserved.