4-(4-hydroxyphenyl)butylcarbamic acid benzyl ester | 587880-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-hydroxyphenyl)butylcarbamic acid benzyl ester
• 英文别名: benzyl [4-(4-hydroxyphenyl)butyl]carbamate；benzyl 4-(4-hydroxypheny)butyl carbamate；benzyl 4-(4-hydroxyphenyl)butylcarbamate；N-Cbz-4-(4-hydroxyphenyl)butylamine；[4-(4-hydroxyphenyl)butyl]carbamic acid benzyl ester；4-(4-Hydroxyphenyl)-N-benzyloxycarbonylbutylamine；N-Cbz4-(4-hydroxyphenyl)butylamine；benzyl N-[4-(4-hydroxyphenyl)butyl]carbamate
• CAS: 587880-25-9
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: JJXKVLJSXQXDGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-hydroxyphenyl)butylcarbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 4-[4-(2,3-propanediol-1-oxy)phenyl]butylamine
  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：

  4-(4-Methoxyphenyl)butylazide 在 水 、 氢溴酸 、 碳酸氢钠 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成 4-(4-hydroxyphenyl)butylcarbamic acid benzyl ester
  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

• [EN] CAPPED PYRAZINOYLGUANIDINE SODIUM CHANNEL BLOCKERS<br/>[FR] INHIBITEURS DE CANAL SODIQUE A PYRAZINOYLGUANIDINE COIFFEE
  申请人：PARION SCIENCES INC

  公开号：WO2005018644A1

  公开（公告）日：2005-03-03

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

  本发明涉及钠通道阻滞剂。本发明还包括使用这些创新性钠通道阻滞剂的各种治疗方法。
• Soluble amide & ester pyrazinoylguanidine sodium channel blockers
  申请人：Johnson R. Michael

  公开号：US20060040954A1

  公开（公告）日：2006-02-23

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

  本发明涉及钠通道阻滞剂。本发明还包括使用这些创新的钠通道阻滞剂进行治疗的各种方法。
• Methods of reducing risk of infection from pathogens with soluble amide and ester pyrazinoylguanidine sodium channel blockers
  申请人：Johnson R. Michael

  公开号：US20070021439A1

  公开（公告）日：2007-01-25

  Prophylactic treatment methods are provided for protection of individuals and/or populations against infection from airborne pathogens. In particular, prophylactic treatment methods are provided comprising administering a sodium channel blocker or pharmaceutically acceptable salts thereof to one or more members of a population at risk of exposure to or already exposed to one or more airborne pathogens, either from natural sources or from intentional release of pathogens into the environment.

  预防性治疗方法旨在保护个人和/或群体免受空气传播病原体感染。具体来说，提供了预防性治疗方法，包括向处于风险暴露或已暴露于一种或多种空气传播病原体的人群中的一个或多个成员施用钠通道阻滞剂或其药用盐。这些病原体可能来自自然源或有意向环境释放病原体。
• DENDRIMER LIKE AMINO AMIDES POSSESSING SODIUM CHANNEL BLOCKER ACTIVITY FOR THE TREATMENT OF DRY EYE AND OTHER MUCOSAL DISEASES
  申请人：PARION SCIENCES, INC.

  公开号：US20130324559A1

  公开（公告）日：2013-12-05

  Sodium channel blockers represented by the formula: are provided where the structural variables are defined herein. The invention also includes a variety of compositions, combinations and methods of treatment using these inventive sodium channel blockers.

  由以下公式代表的钠通道阻滞剂：在此处定义结构变量。 该发明还包括各种组合和使用这些创新性钠通道阻滞剂的治疗方法。
• Sodium channel blockers
  申请人：PARION SCIENCES, Inc.

  公开号：US20040162296A1

  公开（公告）日：2004-08-19

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

  本发明涉及钠通道阻滞剂。本发明还包括使用这些创新性钠通道阻滞剂的各种治疗方法。