4-(3-氨基丙基)苯酚氢溴酸盐 | 583825-30-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(3-氨基丙基)苯酚氢溴酸盐
• 英文名称: 3-(4-Hydroxyphenyl)propylamine hydrobromide
• 英文别名: 4-(3-aminopropyl)phenol Hydrobromide；4-(3-aminopropyl)phenol;hydrobromide
• CAS: 583825-30-3
• 化学式: BrH*C₉H₁₃NO
• mdl: MFCD19380075
• 分子量: 232.12
• InChiKey: WVQGQGNVRPUYBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  46.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3,5-diamino-6-chloropyrazine-2-carbonylcarbamimidothioate hydroiodic acid salt 、 4-(3-氨基丙基)苯酚氢溴酸盐 在 N,N-二异丙基乙胺 作用下， 生成 N-(3,5-diamino-6-chloropyrazine-2-carbonyl)-N''-[3-(4-hydroxyphenyl)propyl]-guanidine
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Novel 2-Substituted Pyrazinoylguanidine Epithelial Sodium Channel Blockers:  Drugs for Cystic Fibrosis and Chronic Bronchitis

  摘要：

  Amiloride (1), the prototypical epithelial sodium channel (ENaC) blocker, has been administered with limited success as aerosol therapy for improving pulmonary function in patients with the genetic disorder cystic fibrosis. This study was conducted to synthesize and identify more potent, less reversible ENaC blockers, targeted for aerosol therapy and possessing minimal systemic renal activity. A series of novel 2-substituted acylguanidine analogues of amiloride were synthesized and evaluated for potency and reversibility on bronchial ENaC. All compounds tested were more potent and less reversible at blocking sodium-dependent shortcircuit current than amiloride. Compounds 30-34 showed the greatest potency on ENaC with IC50 values below 10 nM. A regioselective difference in potency was found (compounds 30, 39, and 40), whereas no stereospecific (compounds 33, 34) difference in potency on ENaC was displayed. Lead compound 32 was 102-fold more potent and 5-fold less reversible than amiloride and displayed the lowest IC50 value ever reported for an ENaC blocker.

  DOI：

  10.1021/jm051134w
• 作为产物：
  描述：

  3-(4-甲氧苯基)-1-丙醇 在 吡啶 、 sodium azide 、 水 、 氢溴酸 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-(3-氨基丙基)苯酚氢溴酸盐
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Novel 2-Substituted Pyrazinoylguanidine Epithelial Sodium Channel Blockers:  Drugs for Cystic Fibrosis and Chronic Bronchitis

  摘要：

  Amiloride (1), the prototypical epithelial sodium channel (ENaC) blocker, has been administered with limited success as aerosol therapy for improving pulmonary function in patients with the genetic disorder cystic fibrosis. This study was conducted to synthesize and identify more potent, less reversible ENaC blockers, targeted for aerosol therapy and possessing minimal systemic renal activity. A series of novel 2-substituted acylguanidine analogues of amiloride were synthesized and evaluated for potency and reversibility on bronchial ENaC. All compounds tested were more potent and less reversible at blocking sodium-dependent shortcircuit current than amiloride. Compounds 30-34 showed the greatest potency on ENaC with IC50 values below 10 nM. A regioselective difference in potency was found (compounds 30, 39, and 40), whereas no stereospecific (compounds 33, 34) difference in potency on ENaC was displayed. Lead compound 32 was 102-fold more potent and 5-fold less reversible than amiloride and displayed the lowest IC50 value ever reported for an ENaC blocker.

  DOI：

  10.1021/jm051134w

文献信息

• Sodium channel blockers
  申请人：CYFI, INC.

  公开号：US20030195160A1

  公开（公告）日：2003-10-16

  The present invention relates to sodium channel blockers. The present invention also relates to a variety of methods of treatment using these sodium channel blockers.

  本发明涉及钠通道阻滞剂。本发明还涉及使用这些钠通道阻滞剂进行治疗的各种方法。
• Methods of using phenolic guanidine sodium channel blockers
  申请人：PARION SCIENCES, Inc.

  公开号：US20040198744A1

  公开（公告）日：2004-10-07

  The present invention relates to sodium channel blockers. The present invention also relates to a variety of methods of treatment using these sodium channel blockers.

  本发明涉及钠通道阻滞剂。本发明还涉及使用这些钠通道阻滞剂的各种治疗方法。
• Phenolic guanidine sodium channel blockers
  申请人：PARION SCIENCES, Inc.

  公开号：US20040204424A1

  公开（公告）日：2004-10-14

  The present invention relates to sodium channel blockers. The present invention also relates to a variety of methods of treatment using these sodium channel blockers.

  本发明涉及钠通道阻滞剂。本发明还涉及使用这些钠通道阻滞剂的各种治疗方法。
• SODIUM CHANNEL BLOCKERS
  申请人：Johnson, Michael R.

  公开号：EP1485359A2

  公开（公告）日：2004-12-15
• EP1485359A4
  申请人：——

  公开号：EP1485359A4

  公开（公告）日：2006-03-22