3-amino-5,6-dichloro 2-pyrazinecarboxamidine | 1366001-21-9

• 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-amino-5,6-dichloro 2-pyrazinecarboxamidine
• 英文别名: 3-Amino-5,6-dichloropyrazine-2-carboximidamide；3-amino-5,6-dichloropyrazine-2-carboximidamide
• CAS: 1366001-21-9
• 化学式: C₅H₅Cl₂N₅
• 分子量: 206.034
• InChiKey: HXXORFKNJLIVPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-5,6-dichloro 2-pyrazinecarboxamidine 、 甘氨酸苄酯对甲苯磺酸盐 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以17%的产率得到5-BnO-Gly 3-amino-6-chloro-2-pyrazinecarboxamidine
  参考文献：
  名称：

  2-Amidino analogs of glycine–amiloride conjugates: Inhibitors of urokinase-type plasminogen activator

  摘要：

  The relative non-toxicity of the diuretic amiloride, coupled with its selective inhibition of the protease urokinase plasminogen activator (uPA), makes this compound class attractive for structure-activity studies. Herein we substituted the C(2)-acylguanidine of C(5)-glycyl-amiloride with amidine and amidoxime groups. The data show the importance of maintaining C(5)-hydrophobicity. The C(5)-benzylglycine analogs containing either C(2)-acylguanidine or amidine inhibited uPA with an IC50 ranging from 3 to 7 mu M and were cytotoxic to human U87 malignant glioma cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.123
• 作为产物：
  描述：

  3-氨基-5,6-二氯吡嗪-2-甲腈 在 三甲基铝 、 氯化铵 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 32.0h， 以95%的产率得到3-amino-5,6-dichloro 2-pyrazinecarboxamidine
  参考文献：
  名称：

  2-Amidino analogs of glycine–amiloride conjugates: Inhibitors of urokinase-type plasminogen activator

  摘要：

  The relative non-toxicity of the diuretic amiloride, coupled with its selective inhibition of the protease urokinase plasminogen activator (uPA), makes this compound class attractive for structure-activity studies. Herein we substituted the C(2)-acylguanidine of C(5)-glycyl-amiloride with amidine and amidoxime groups. The data show the importance of maintaining C(5)-hydrophobicity. The C(5)-benzylglycine analogs containing either C(2)-acylguanidine or amidine inhibited uPA with an IC50 ranging from 3 to 7 mu M and were cytotoxic to human U87 malignant glioma cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.123

文献信息

• 2-Amidino analogs of glycine–amiloride conjugates: Inhibitors of urokinase-type plasminogen activator
  作者：Archna P. Massey、William R. Harley、NagaRekha Pasupuleti、Fredric A. Gorin、Michael H. Nantz

  DOI：10.1016/j.bmcl.2011.12.123

  日期：2012.4

  The relative non-toxicity of the diuretic amiloride, coupled with its selective inhibition of the protease urokinase plasminogen activator (uPA), makes this compound class attractive for structure-activity studies. Herein we substituted the C(2)-acylguanidine of C(5)-glycyl-amiloride with amidine and amidoxime groups. The data show the importance of maintaining C(5)-hydrophobicity. The C(5)-benzylglycine analogs containing either C(2)-acylguanidine or amidine inhibited uPA with an IC50 ranging from 3 to 7 mu M and were cytotoxic to human U87 malignant glioma cells. (C) 2011 Elsevier Ltd. All rights reserved.