N-Cbz-4-(4-allyloxyphenyl)butylamine | 587880-26-0

• 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: N-Cbz-4-(4-allyloxyphenyl)butylamine
• 英文别名: [4-(4-allyloxyphenyl)butyl]carbamic acid benzyl ester；benzyl N-[4-(4-prop-2-enoxyphenyl)butyl]carbamate
• CAS: 587880-26-0
• 化学式: C₂₁H₂₅NO₃
• 分子量: 339.434
• InChiKey: ZPZKMJSRZHEDMX-UHFFFAOYSA-N

物化性质

• 沸点：
  505.2±45.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Cbz-4-(4-allyloxyphenyl)butylamine 在 palladium on activated charcoal 硼烷四氢呋喃络合物 、 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 3-[4-(4-Aminobutyl)phenoxy]-1-propanol
  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 sodium hydroxide 、 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 N-Cbz-4-(4-allyloxyphenyl)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

文献信息

• 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。
• SODIUM CHANNEL BLOCKERS
  申请人：PARION SCIENCES, INC.

  公开号：US20150376146A1

  公开（公告）日：2015-12-31

  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。
• Methods of using sodium channel blockers
  申请人：PARION SCIENCES, Inc.

  公开号：US20040198749A1

  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 the sodium channel blockers.

  本发明涉及钠通道阻滞剂。同时，本发明还涉及使用钠通道阻滞剂的多种治疗方法。
• Hetero substitued sodium channel blockers
  申请人：Johnson R. Michael

  公开号：US20060142581A1

  公开（公告）日：2006-06-29

  The present invention relates to novel pyrazinoylguanidine compounds and methods of using the same.

  本发明涉及新型吡嗪酰基胍化合物及其使用方法。
• METHODS OF USING SODIUM CHANNEL BLOCKERS
  申请人：Johnson R. Michael

  公开号：US20070265280A1

  公开（公告）日：2007-11-15

  The present invention relates to use of a compound represented by formula (I): in which at least one of R 3 and R 4 is a group represented by formula (A): where the structural variables are as defined herein. The compounds are useful for blocking sodium channels and treating a variety of conditions.

  本发明涉及使用式（I）所表示的化合物： 其中R3和R4中至少有一个是由式（A）所表示的基团： 其中结构变量如本文所定义。该化合物可用于阻断钠通道并治疗多种疾病。