(1-naphthylmethyl)guanidine hydrochloride | 6047-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1-naphthylmethyl)guanidine hydrochloride
• 英文别名: 1-(naphthalen-1-ylmethyl)guanide hydrochloride；1-(Naphthylmethyl)guanidine hydrochloride；diaminomethylidene(naphthalen-1-ylmethyl)azanium;chloride
• CAS: 6047-71-8
• 化学式: C₁₂H₁₃N₃*ClH
• 分子量: 235.716
• InChiKey: NTSSUHAQSUMJCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-naphthylmethyl)guanidine hydrochloride 在 盐酸 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 2.58h， 生成 N-(2-amino-5-chlorobenzoyl)-N'-(1-naphthylmethyl)guanidine hydrochloride
  参考文献：
  名称：

  Novel inhibitors of the sodium–calcium exchanger: benzene ring analogues of N-guanidino substituted amiloride derivatives

  摘要：

  A series of N-guanidino substituted 2,4-diamino-5-carbonylguanidine molecules related to amiloride were synthesised and, evaluated for their ability to inhibit the sodium-calcium exchanger in rat insulinoma cells (RINm5F) and human platelets. Specific chemical pathways were used to prepare the benzene derivatives designed as bioisosteric analogues of the pyrazine derivatives of amiloride. Several so-called 'simplified analogues', where some substituents of amiloride were omitted or replaced, were also prepared and included in the biological evaluation. The inhibitory potency of the sodium-calcium exchanger was screened on both cell types by measuring their effect on Ca-45(2+) uptake. Among the most active compounds, N-(2 -amino-5-chloro-4-nitrobenzoyl)-N'-(1-naphtylmethyl)guanidine (IC50 = 3.4 muM) was found more active than amiloride (IC50 = 690 muM) and 3,4-dichlorobenzamil (IC50 = 15.2 muM), the reference inhibitor. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01247-8