3,5-二氨基-6-氯吡嗪-2-甲酰肼 | 6015-74-3

• 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: 3,5-二氨基-6-氯吡嗪-2-甲酰肼
• 英文名称: 3,5-diamino-6-chloropyrazine-2-carbohydrazide
• 英文别名: 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid hydrazide
• CAS: 6015-74-3
• 化学式: C₅H₇ClN₆O
• 分子量: 202.603
• InChiKey: NEZIXHJJWOFFOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 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：
  133
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2-phenylethyl)]-3-cyanoguanidine 、 3,5-二氨基-6-氯吡嗪-2-甲酰肼 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以62%的产率得到1-(3,5-diamino-6-chloropyrazinamido)-5-[2-phenylethyl]biguanide
  参考文献：
  名称：

  BIGUANIDE DERIVATIVE COMPOUND

  摘要：

  公开号：

  EP2647630B1
• 作为产物：
  描述：

  3,5-二氨基-6-氯吡嗪-2-羧酸甲酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 以81%的产率得到3,5-二氨基-6-氯吡嗪-2-甲酰肼
  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

• HETEROCYCLIC COMPOUNDS, MEDICAMENTS CONTAINING SAID COMPOUNDS, USE THEREOF AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：HECKEL Armin

  公开号：US20130157981A1

  公开（公告）日：2013-06-20

  The present invention relates to compounds of general formula (I) and the tautomers and the salts thereof, particularly the pharmaceutically acceptable salts thereof with inorganic or organic acids and bases, which have valuable pharmacological properties, particularly an inhibitory effect on epithelial sodium channels, the use thereof for the treatment of diseases, particularly diseases of the lungs and airways.

  本发明涉及一般式（I）的化合物，以及其互变异构体和盐，特别是其与无机或有机酸和碱形成的药用可接受盐，具有有价值的药理特性，特别是对上皮钠通道具有抑制作用，以及其用于治疗疾病，特别是肺部和气道疾病的用途。
• [EN] HETEROCYCLIC COMPOUNDS, MEDICAMENTS CONTAINING SAID COMPOUNDS, USE THEREOF AND PROCESSES FOR THE PREPARATION THEREOF<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES, MÉDICAMENTS CONTENANT LESDITS COMPOSÉS, UTILISATION DE CEUX-CI ET PROCÉDÉS POUR LA PRÉPARATION DE CEUX-CI
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2013092674A1

  公开（公告）日：2013-06-27

  The present invention relates to compounds of general formula (I) and the tautomers and the salts thereof, particularly the pharmaceutically acceptable salts thereof with inorganic or organic acids and bases, which have valuable pharmacological properties, particularly an inhibitory effect on epithelial sodium channels, the use thereof for the treatment of diseases, particularly diseases of the lungs and airways.

  本发明涉及一般式(I)的化合物，以及其互变异构体和盐，特别是其与无机或有机酸和碱形成的药用盐，具有有价值的药理特性，特别是对上皮钠通道具有抑制作用，其用于治疗疾病，特别是肺部和气道疾病。
• [EN] HETEROCYCLIC COMPOUNDS, MEDICAMENTS CONTAINING SAID COMPOUNDS, USE THEREOF AND PROCESSES FOR THE PREPARATION THEREOF<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES, MÉDICAMENTS CONTENANT LESDITS COMPOSÉS, LEUR UTILISATION ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2013064450A1

  公开（公告）日：2013-05-10

  The present invention relates to compounds of general formula (I) and the tautomers and the salts thereof, particularly the pharmaceutically acceptable salts thereof with inorganic or organic acids and bases, which have valuable pharmacological properties, particularly an inhibitory effect on epithelial sodium channels, the use thereof for the treatment of diseases, particularly diseases of the lungs and airways.

  本发明涉及一般式(I)的化合物，其互变异构体和盐，特别是其与无机或有机酸和碱形成的药用盐，具有有价值的药理特性，特别是对上皮钠通道的抑制作用，以及其用于治疗疾病，特别是肺部和呼吸道疾病的用途。
• US8895564B2
  申请人：——

  公开号：US8895564B2

  公开（公告）日：2014-11-25
• 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.