N-amidino-3,5-diamino-6-iodo-2-pyrazinecarboxamide hydrochloride

• 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: N-amidino-3,5-diamino-6-iodo-2-pyrazinecarboxamide hydrochloride
• 英文别名: 3,5-diamino-N-carbamimidoyl-6-iodopyrazine-2-carboxamide;hydrochloride
• 化学式: C₆H₈IN₇O*ClH
• 分子量: 357.541
• InChiKey: OISRMKAPQONEBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.92
• 重原子数：
  16
• 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：
  159
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-amidino-3,5-diamino-6-iodo-2-pyrazinecarboxamide hydrochloride 、 三氟甲烷硫醇铜 生成 N-amidino-3,5-diamino-6-trifluoromethylthio-2-pyrazinecarboxamide
  参考文献：
  名称：

  6-Substituted amiloride derivatives

  摘要：

  N-氨基甲酰基-3,5-二氨基-6-取代-2-吡嗪羧酰胺及其合成方法。

  公开号：

  US04196292A1
• 作为产物：
  描述：

  盐酸阿米洛利 在 N-碘代丁二酰亚胺 、 palladium on activated charcoal 、 氢气 、 magnesium oxide 作用下， 生成 N-amidino-3,5-diamino-6-iodo-2-pyrazinecarboxamide hydrochloride
  参考文献：
  名称：

  Synthesis and preliminary evaluation of amiloride analogs as inhibitors of the urokinase-type plasminogen activator (uPA)

  摘要：

  A known side-activity of the oral potassium-sparing diuretic drug amiloride is inhibition of the enzyme urokinase-type plasminogen activator (uPA, K-i = 7 mu M), a promising anticancer target. Several studies have demonstrated significant antitumor/metastasis properties for amiloride in animal cancer models and it would appear that these arise, at least in part, through inhibition of uPA. Selective optimization of amiloride's structure for more potent inhibition of uPA and loss of diuretic effects would thus appear as an attractive strategy towards novel anticancer agents. The following report is a preliminary structure-activity exploration of amiloride analogs as inhibitors of uPA. A key finding was that the well-studied 5-substituted analogs ethylisopropyl amiloride (EIPA) and hexamethylene amiloride (HMA) are approximately twofold more potent than amiloride as uPA inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.044

文献信息

• New N-amidino-3,5-diamino-6-substituted-2-pyrazinecarboxamides and process for preparing same
  申请人：Merck & Co., Inc.

  公开号：EP0000200A1

  公开（公告）日：1979-01-10

  N-Amidino-3,5- diamino-6- substituted-2- pyrazihecar- boxamides and a process for their synthesis.

  N-脒基-3,5-二脒基-6-取代-2-吡嗪羧酰胺及其合成工艺。
• US4196292A
  申请人：——

  公开号：US4196292A

  公开（公告）日：1980-04-01
• Synthesis and preliminary evaluation of amiloride analogs as inhibitors of the urokinase-type plasminogen activator (uPA)
  作者：Hayden Matthews、Marie Ranson、Joel D.A. Tyndall、Michael J. Kelso

  DOI：10.1016/j.bmcl.2011.09.044

  日期：2011.11

  A known side-activity of the oral potassium-sparing diuretic drug amiloride is inhibition of the enzyme urokinase-type plasminogen activator (uPA, K-i = 7 mu M), a promising anticancer target. Several studies have demonstrated significant antitumor/metastasis properties for amiloride in animal cancer models and it would appear that these arise, at least in part, through inhibition of uPA. Selective optimization of amiloride's structure for more potent inhibition of uPA and loss of diuretic effects would thus appear as an attractive strategy towards novel anticancer agents. The following report is a preliminary structure-activity exploration of amiloride analogs as inhibitors of uPA. A key finding was that the well-studied 5-substituted analogs ethylisopropyl amiloride (EIPA) and hexamethylene amiloride (HMA) are approximately twofold more potent than amiloride as uPA inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.
• 6-Substituted amiloride derivatives
  申请人：Merck & Co., Inc.

  公开号：US04196292A1

  公开（公告）日：1980-04-01

  N-amidino-3,5-diamino-6-substituted-2-pyrazinecarboxamides and a process for their synthesis.

  N-氨基甲酰基-3,5-二氨基-6-取代-2-吡嗪羧酰胺及其合成方法。