5-BnO-Gly 3-amino-6-chloro-2-pyrazinecarboxamide | 1115177-13-3

• 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: 5-BnO-Gly 3-amino-6-chloro-2-pyrazinecarboxamide
• 英文别名: amide-Am-C(5)-Gly-OBn；Benzyl 2-[(6-amino-5-carbamoyl-3-chloropyrazin-2-yl)amino]acetate
• CAS: 1115177-13-3
• 化学式: C₁₄H₁₄ClN₅O₃
• 分子量: 335.75
• InChiKey: HJPSTKDYBOZZJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-氨基-5,6-二氯-2-吡嗪羧酸甲脂 在 氨 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 29.5h， 生成 5-BnO-Gly 3-amino-6-chloro-2-pyrazinecarboxamide
  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.