3-(4-chlorobenzyloxy)pyrazin-2-amine | 126993-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-(4-chlorobenzyloxy)pyrazin-2-amine
• 英文别名: 3-[(4-Chlorophenyl)methoxy]-2-pyrazinamine；3-[(4-chlorophenyl)methoxy]pyrazin-2-amine
• CAS: 126993-73-5
• 化学式: C₁₁H₁₀ClN₃O
• 分子量: 235.673
• InChiKey: WWSUJJYOIOTNSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-chlorobenzyloxy)pyrazin-2-amine 、 1-Alapha-萘异氰酸酯 以 四氢呋喃 、 mineral oil 为溶剂， 以60.8%的产率得到1-(3-(4-chlorobenzyloxy)pyrazin-2-yl)-3-(naphthalen-1-yl)urea
  参考文献：
  名称：

  Pyrazinyl ureas revisited: 1-(3-(Benzyloxy)pyrazin-2-yl)-3-(3,4-dichlorophenyl)urea, a new blocker of Aβ-induced mPTP opening for Alzheimer's disease

  摘要：

  Herein, we report synthesis and evaluation of new twenty-eight pyrazinyl ureas against beta amyloid (A beta) induced opening of mitochondrial permeability transition pore (mPTP) using JC-1 assay which measures the change of mitochondrial membrane potential (Delta Psi m). The neuroprotective effect of seventeen compounds against A beta-induced mPTP opening was superior to that of the standard Cyclosporin A (CsA). Among them, 1-(3-(benzyloxy)pyrazin-2-yl)-3-(3,4-dichlorophenyl)urea (5) effectively maintained mitochondrial function and cell viabilities on ATP assay and MIT assay. Also, hERG channel assay presented safe cardiotoxicity profile for compound 5. In addition, using CDocker algorithm, a molecular docking model presented a plausible explanation for the elicited differences in efficiencies of the synthesized compounds to reduce the green to red fluorescence as indication of mPTP closure. Hence, this report presents compound 5 as the most promising pyrazinyl urea-based mPTP blocker up to date. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.068
• 作为产物：
  描述：

  2-氯-3-氨基吡嗪 、 4-氯苯甲醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 16.0h， 以38.1%的产率得到3-(4-chlorobenzyloxy)pyrazin-2-amine
  参考文献：
  名称：

  Pyrazinyl ureas revisited: 1-(3-(Benzyloxy)pyrazin-2-yl)-3-(3,4-dichlorophenyl)urea, a new blocker of Aβ-induced mPTP opening for Alzheimer's disease

  摘要：

  Herein, we report synthesis and evaluation of new twenty-eight pyrazinyl ureas against beta amyloid (A beta) induced opening of mitochondrial permeability transition pore (mPTP) using JC-1 assay which measures the change of mitochondrial membrane potential (Delta Psi m). The neuroprotective effect of seventeen compounds against A beta-induced mPTP opening was superior to that of the standard Cyclosporin A (CsA). Among them, 1-(3-(benzyloxy)pyrazin-2-yl)-3-(3,4-dichlorophenyl)urea (5) effectively maintained mitochondrial function and cell viabilities on ATP assay and MIT assay. Also, hERG channel assay presented safe cardiotoxicity profile for compound 5. In addition, using CDocker algorithm, a molecular docking model presented a plausible explanation for the elicited differences in efficiencies of the synthesized compounds to reduce the green to red fluorescence as indication of mPTP closure. Hence, this report presents compound 5 as the most promising pyrazinyl urea-based mPTP blocker up to date. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.068