3-(2-aminoethyloxy)-4-phenylfurazan | 204335-73-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-aminoethyloxy)-4-phenylfurazan
• 英文别名: 2-[(4-phenyl-1,2,5-oxadiazol-3-yl)oxy]ethanamine
• CAS: 204335-73-9
• 化学式: C₁₀H₁₁N₃O₂
• 分子量: 205.216
• InChiKey: GECPOBSASKPDCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.17
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(2-aminoethyloxy)-4-phenylfurazan 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.08h， 生成 1-(1-naphthyloxy)-3-[2-(3-phenyl-4-furazanyloxy)ethylamino]propan-2-ol
  参考文献：
  名称：

  摘要：

  Purpose. A series of derivatives having a propranolol-like moiety linked to NO-donor furoxan substructures were synthesized. The main objective of this investigation was to obtain agents with mixed No-dependent vasodilating and beta-blocking activities.Methods. Most of the target compounds were synthesized from the appropriate furoxans bearing XCH2CH2NH2 (X = O, S, SO2) chains at the 4 position of the ring, using AI(C2H5)(3) in methylene chloride solution and (+/-)2,3-epoxypropyl 1-naphtyl ether. Two of the final products (X = CONH) were obtained by coupling the appropriate furoxancarboxylic acids with N-[2-hydroxy-3-(1-naphthoxy)propyl]ethylenediamine. beta(1)- and beta(2)-blocking activities were examined on isolated guinea pig right atria and on guinea pig trachea respectively. Vasodilating properties were assessed on endothelium denuded strips of rat aortaResult. Some derivatives behave as well balanced "hybrids" displaying NO-dependent vasodilating and beta-blocking properties in the same concentration range. Some others display either prevalent beta-blocking or vasodilating activity. Generally speaking hybrid formation lowers the affinity for beta-receptors, in particular for beta(2)-type, to give an increase in beta(1)/beta(2) selectivity.Conclusions. The furoxan system is a flexible tool in designing analogues of propranolol whose NO-donating and beta-blocking properties are modulated over a wide range.

  DOI：

  10.1023/a:1012136030849
• 作为产物：
  描述：

  3-nitro-4-phenylfurazane 、 C.I.酸性橙108 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 以80%的产率得到3-(2-aminoethyloxy)-4-phenylfurazan
  参考文献：
  名称：

  摘要：

  Purpose. A series of derivatives having a propranolol-like moiety linked to NO-donor furoxan substructures were synthesized. The main objective of this investigation was to obtain agents with mixed No-dependent vasodilating and beta-blocking activities.Methods. Most of the target compounds were synthesized from the appropriate furoxans bearing XCH2CH2NH2 (X = O, S, SO2) chains at the 4 position of the ring, using AI(C2H5)(3) in methylene chloride solution and (+/-)2,3-epoxypropyl 1-naphtyl ether. Two of the final products (X = CONH) were obtained by coupling the appropriate furoxancarboxylic acids with N-[2-hydroxy-3-(1-naphthoxy)propyl]ethylenediamine. beta(1)- and beta(2)-blocking activities were examined on isolated guinea pig right atria and on guinea pig trachea respectively. Vasodilating properties were assessed on endothelium denuded strips of rat aortaResult. Some derivatives behave as well balanced "hybrids" displaying NO-dependent vasodilating and beta-blocking properties in the same concentration range. Some others display either prevalent beta-blocking or vasodilating activity. Generally speaking hybrid formation lowers the affinity for beta-receptors, in particular for beta(2)-type, to give an increase in beta(1)/beta(2) selectivity.Conclusions. The furoxan system is a flexible tool in designing analogues of propranolol whose NO-donating and beta-blocking properties are modulated over a wide range.

  DOI：

  10.1023/a:1012136030849

文献信息

• Nicorandil analogues containing NO-donor furoxans and related furazans
  作者：Donatella Boschi、Clara Cena、Antonella Di Stilo、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/s0968-0896(00)00098-5

  日期：2000.7

  The synthesis and in vitro vasodilating properties of hybrid compounds in which furoxan (1,2,5-oxadiazole 2-oxide) moieties, endowed with different NO-donor properties, were substituted for the nitroxy function of Nicorandil are reported. The corresponding cyanoguanidine analogues are also considered. This approach has led to a series of vasorelaxing compounds devoid of affinity for K-ATP channels, whose activity is prevalently due to their ability to activate sGC, at the concentrations of the experiments. Related furazan (1,2,5-oxadiazole) derivatives, unable to release nitric oxide were also prepared and studied for control. The amide analogues of Nicorandil display feeble vasorelaxing action not involving the activation of K+ channels, while in the guanidine analogues, this mechanism seems to underlie this action. (C) 2000 Elsevier Science Ltd. All rights reserved.