N-thieno[2,3-b]thieno-2-yl-L-Glu[NH-2-(1-benzylpiperidin-4-yl)ethyl]-O-nHex | 1161426-70-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-thieno[2,3-b]thieno-2-yl-L-Glu[NH-2-(1-benzylpiperidin-4-yl)ethyl]-O-nHex
• 英文别名: (S)-hexyl 5-(2-(1-benzylpiperidin-4-yl)ethylamino)-5-oxo-2-(thieno[2,3-b]thiophene-2-carboxamido)pentanoate；hexyl (2S)-5-[2-(1-benzylpiperidin-4-yl)ethylamino]-5-oxo-2-(thieno[2,3-b]thiophene-5-carbonylamino)pentanoate
• CAS: 1161426-70-5
• 化学式: C₃₂H₄₃N₃O₄S₂
• 分子量: 597.843
• InChiKey: ONGQTEYIIKGJGV-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  thieno[2,3-b]thiophene-2-carbonyl chloride 、 L-Glu[NH-2-(1-benzylpiperidin-4-yl)ethyl]-O-nHex, trifluoroacetic salt 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到N-thieno[2,3-b]thieno-2-yl-L-Glu[NH-2-(1-benzylpiperidin-4-yl)ethyl]-O-nHex
  参考文献：
  名称：

  Neuroprotective and Cholinergic Properties of Multifunctional Glutamic Acid Derivatives for the Treatment of Alzheimer’s Disease

  摘要：

  Novel multifunctional compounds have been designed, synthesized, and evaluated as potential drugs for the treatment of Alzheimer's disease (AD). With an L-glutamic moiety as a suitable biocompatible linker, three pharmacophoric groups were joined: (I) an N-benzylpiperidine fragment selected to inhibit acetylcholinesterase by interacting with the catalytic active site (CAS), (2) an N-protecting group of the amino acid, capable of interacting with the acetylcholinesterase (AChE)-peripheral anionic site (PAS) and protecting neurons against oxidative stress, and (3) a lipophilic alkyl ester that would facilitate penetration into the central nervous system by crossing the blood-brain barrier. At submicromolar concentration, they inhibit ACNE and butyrylcholinesterase (BuChE) of human origin, displace the binding of propidium iodide from the PAS of ACNE, and could thus inhibit A beta aggregation promoted by ACNE. They also display neuroprotective properties against mitochondrial free radicals, show low toxicity, and could be able to penetrate into the CNS.

  DOI：

  10.1021/jm900628z