1-(5-Hydroxypentyl)-3-(2-mercaptoethyl)guanidine | 1427191-11-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(5-Hydroxypentyl)-3-(2-mercaptoethyl)guanidine
• 英文别名: 2-(5-Hydroxypentyl)-1-(2-sulfanylethyl)guanidine；2-(5-hydroxypentyl)-1-(2-sulfanylethyl)guanidine
• CAS: 1427191-11-4
• 化学式: C₈H₁₉N₃OS
• 分子量: 205.324
• InChiKey: RAAWNOMKDUNNKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  71.6
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-2-噻唑啉 、 5-氨基-1-戊醇 在 氢溴酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 生成 1-(5-Hydroxypentyl)-3-(2-mercaptoethyl)guanidine
  参考文献：
  名称：

  Neuroprotective effects of mercaptoethylleonurine and mercaptoethylguanidine analogs on hydrogen peroxide-induced apoptosis in human neuronal SH-SY5Y cells

  摘要：

  A series of mercaptoethylleonurine and mercaptoethylguanidine derivatives were designed and synthesized. Their neuroprotective effects toward H2O2-induced apoptosis were investigated in human SH-SY5Y cells. The results from these studies identified several potent compounds, with compound 8k emerging as the most effective. Further investigation demonstrated that 8k reduced H2O2-induced activation of mitochondrial apoptosis by inhibiting the expression of Bax and elevating the expression of Bcl-2. Moreover, the molecular mechanism underlying the observed neuroprotective effects of 8k was exerted via the Akt and JNK pathways. Compound 8k can be a lead compound for further discovery of neuroprotective medicine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.038

文献信息

• Neuroprotective effects of mercaptoethylleonurine and mercaptoethylguanidine analogs on hydrogen peroxide-induced apoptosis in human neuronal SH-SY5Y cells
  作者：Zhao-Lin Que、Wen-Jiang Zhou、Jun Chang、Xin-Hua Liu、Jian-Ming Yu、Xun Sun

  DOI：10.1016/j.bmcl.2013.01.038

  日期：2013.3

  A series of mercaptoethylleonurine and mercaptoethylguanidine derivatives were designed and synthesized. Their neuroprotective effects toward H2O2-induced apoptosis were investigated in human SH-SY5Y cells. The results from these studies identified several potent compounds, with compound 8k emerging as the most effective. Further investigation demonstrated that 8k reduced H2O2-induced activation of mitochondrial apoptosis by inhibiting the expression of Bax and elevating the expression of Bcl-2. Moreover, the molecular mechanism underlying the observed neuroprotective effects of 8k was exerted via the Akt and JNK pathways. Compound 8k can be a lead compound for further discovery of neuroprotective medicine. (C) 2013 Elsevier Ltd. All rights reserved.