2-Amino-1-heptyl-1-methylguanidine | 769090-58-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Amino-1-heptyl-1-methylguanidine
• 英文别名: 2-amino-1-heptyl-1-methylguanidine
• CAS: 769090-58-6
• 化学式: C₉H₂₂N₄
• mdl: MFCD19202732
• 分子量: 186.3
• InChiKey: FZWLYLZRPXHJAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Amino-1-heptyl-1-methylguanidine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 1-heptyl-2-[(E)-(5-hydroxy-1H-indol-3-yl)methylideneamino]-1-methylguanidine
  参考文献：
  名称：

  The Serotonin 5-HT4 Receptor. 2. Structure-Activity Studies of the Indole Carbazimidamide Class of Agonists

  摘要：

  A number of substituted indole carbazimidamides were prepared and evaluated as 5-HT4 receptor agonists by using the isolated field-stimulated guinea pig ileum preparation. Their selectivity for the 5-HT4 receptor was established by examining their affinity for other 5-HT receptors using radioligand-binding techniques. Several selective and highly potent full as well as partial agonists emerged from this study. For example, 1b,d were found to be the most potent, full 5-HT4 receptor agonists described so far (EC(50) = 0.5 and 0.8 nM, respectively), being 6 and 4 times more potent than serotonin itself. On the other hand, 5b and 1h appeared as partial 5-HT4 receptor agonists in the nonstimulated guinea pig ileum preparation with potencies, evaluated against serotonin action, respectively similar (5b, K-i = 12 nM) to and 300-fold higher (1h, K-i = 0.04 nM) than serotonin.

  DOI：

  10.1021/jm00013a010
• 作为产物：
  描述：

  N-甲基庚胺 在 盐酸 、 ammonium hydroxide 、 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.25h， 生成 2-Amino-1-heptyl-1-methylguanidine
  参考文献：
  名称：

  The Serotonin 5-HT4 Receptor. 2. Structure-Activity Studies of the Indole Carbazimidamide Class of Agonists

  摘要：

  A number of substituted indole carbazimidamides were prepared and evaluated as 5-HT4 receptor agonists by using the isolated field-stimulated guinea pig ileum preparation. Their selectivity for the 5-HT4 receptor was established by examining their affinity for other 5-HT receptors using radioligand-binding techniques. Several selective and highly potent full as well as partial agonists emerged from this study. For example, 1b,d were found to be the most potent, full 5-HT4 receptor agonists described so far (EC(50) = 0.5 and 0.8 nM, respectively), being 6 and 4 times more potent than serotonin itself. On the other hand, 5b and 1h appeared as partial 5-HT4 receptor agonists in the nonstimulated guinea pig ileum preparation with potencies, evaluated against serotonin action, respectively similar (5b, K-i = 12 nM) to and 300-fold higher (1h, K-i = 0.04 nM) than serotonin.

  DOI：

  10.1021/jm00013a010

文献信息

• Aminoguanidines
  申请人：SANDOZ LTD.

  公开号：EP0505322A1

  公开（公告）日：1992-09-23

  Compounds of formula         A-X--Y-NH-B wherein A is derived from optionally substituted benzothiophene, indole, 4-aza-and 7-aza-benzothiophene or-indole, A bearing in position 5 hydrogen, halogen, optionally substituted alkyl, hydroxy, nitro, amino, alkylamino, acylamino, alcoxycarbonyl, sulfamoyl, cyano, trimethylsilyl, carboxy, carbamoyl, phosphate, oxycarbamoyl, heterocyclic radical or ether or ester group, X---Y is -CR₈=N- or CH(R₈)-NH- wherein R₈ is -H or alkyl and attached at position 3 of A, and B is a heterocyclic radical or a residue wherein R₁₀ is H, optionally substituted alkyl, cycloalkyl, aryl, adamantyl, acyl or carbamoyl and X₂ is alkylthio or NR₃R₁₀ wherein R₃ is H or alkyl or R₃ and R₁₀ together with the nitrogen atom to which they are attached form a heterocyclic radical, in free form or in salt form, have pharmacological activity, e.g. for treating gastrointestinal disorders.

  式的化合物 A-X--Y-NH-B 其中 A 来自任选取代的苯并噻吩、吲哚、4-氮杂和 7-氮杂苯并噻吩或吲哚，A 在第 5 位含有氢、卤素、任选取代的烷基、羟基、硝基、氨基、烷基氨基、酰氨基、烷氧基羰基、氨基磺酰基、氰基、三甲基硅基、羧基、氨基甲酰基、磷酸基、氧氨基甲酰基、杂环基或醚或酯基、氰基、三甲基硅基、羧基、氨基甲酰基、磷酸基、氧氨基甲酰基、杂环基、醚基或酯基，X--Y 是-CR₈=N- 或 CH(R₈)-NH- 其中 R₈ 是-H 或烷基并连接在 A 的第 3 位，B 是杂环基或残基。 其中 R₁₀ 是 H、任选取代的烷基、环烷基、芳基、金刚烷基、酰基或氨基甲酰基、X₂是烷硫基或 NR₃R₁₀，其中 R₃ 是 H 或烷基，或 R₃ 和 R₁₀ 与它们连接的氮原子一起形成杂环基。例如，用于治疗胃肠道疾病。
• The Serotonin 5-HT4 Receptor. 2. Structure-Activity Studies of the Indole Carbazimidamide Class of Agonists
  作者：Karl-Heinz Buchheit、Rainer Gamse、Rudolf Giger、Daniel Hoyer、Francois Klein、Edgar Kloeppner、Hans-Juergen Pfannkuche、Henri Mattes

  DOI：10.1021/jm00013a010

  日期：1995.6

  A number of substituted indole carbazimidamides were prepared and evaluated as 5-HT4 receptor agonists by using the isolated field-stimulated guinea pig ileum preparation. Their selectivity for the 5-HT4 receptor was established by examining their affinity for other 5-HT receptors using radioligand-binding techniques. Several selective and highly potent full as well as partial agonists emerged from this study. For example, 1b,d were found to be the most potent, full 5-HT4 receptor agonists described so far (EC(50) = 0.5 and 0.8 nM, respectively), being 6 and 4 times more potent than serotonin itself. On the other hand, 5b and 1h appeared as partial 5-HT4 receptor agonists in the nonstimulated guinea pig ileum preparation with potencies, evaluated against serotonin action, respectively similar (5b, K-i = 12 nM) to and 300-fold higher (1h, K-i = 0.04 nM) than serotonin.