amidine-Am-C(5)-Gly-OH | 1115176-94-7

• 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: amidine-Am-C(5)-Gly-OH
• 英文别名: 5-HO-Gly 3-amino-6-chloro-2-pyrazineamidine；2-[(6-Amino-5-carbamimidoyl-3-chloropyrazin-2-yl)amino]acetic acid
• CAS: 1115176-94-7
• 化学式: C₇H₉ClN₆O₂
• 分子量: 244.64
• InChiKey: VOABQIDJSPEYJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-BnO-Gly 3-amino-6-chloro-2-pyrazinecarboxamidine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 32.0h， 以55%的产率得到amidine-Am-C(5)-Gly-OH
  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

• INHIBITORS OF INTRACELLULAR UROKINASE PLASMINOGEN ACTIVATOR AND METHODS OF USE THEREOF
  申请人：Gorin Fredric A.

  公开号：US20120108494A1

  公开（公告）日：2012-05-03

  The present invention provides compositions comprising amiloride amino acid and peptide conjugates. Efficient methods are also provided for administering the compositions for treating cancer and for delivering an amiloride conjugate into cancer cells in a subject in need thereof.
• US8546322B2
  申请人：——

  公开号：US8546322B2

  公开（公告）日：2013-10-01
• [EN] INHIBITORS OF INTRACELLULAR UROKINASE PLASMINOGEN ACTIVATOR AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS D'ACTIVATEUR DU PLASMINOGÈNE DE TYPE UROKINASE INTRACELLULAIRE ET PROCÉDÉS D'UTILISATION
  申请人：UNIV CALIFORNIA

  公开号：WO2009020877A2

  公开（公告）日：2009-02-12

  The present invention provides compositions comprising amiloride amino acid and peptide conjugates. Efficient methods are also provided for administering the compositions for treating cancer and for delivering an amiloride conjugate into cancer cells in a subject in need thereof.
• 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.