EIPA盐酸盐 | 1345839-28-2

• 物质功能分类: 生物化工 - 抑制剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: EIPA盐酸盐
• 英文名称: ethylisopropyl amiloride hydrochloride
• 英文别名: 3-amino-N-carbamimidoyl-6-chloro-5-[ethyl(propan-2-yl)amino]pyrazine-2-carboxamide;hydrochloride
• CAS: 1345839-28-2
• 化学式: C₁₁H₁₈ClN₇O*ClH
• 分子量: 336.224
• InChiKey: BGHBOQNLQNKPFO-UHFFFAOYSA-N

物化性质

• 溶解度：
  二甲基亚砜：130 mg/mL（386.65 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  137
• 氢给体数：
  4
• 氢受体数：
  5

制备方法与用途

生物活性

EIPA 氢氯化物（L593754 氢氯化物）是一种 TRPP3 阳离子通道抑制剂，其 IC50 值为 10.5 μM。此外，EIPA 氢氯化物还能够抑制 Na+/H+ 交换器 (NHE) 和巨噬细胞的巨胞饮作用。

靶点

• IC50: 10.5 μM (TRPP3 阳离子通道)
• NHE
• 巨胞饮作用

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 sodium 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 EIPA盐酸盐
  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

• 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.