N-[N-[4-(1H-imidazol-5-yl)butyl]-N'-[3-(1H-imidazol-5-yl)propyl]carbamimidoyl]benzamide | 81282-29-3

• 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-[N-[4-(1H-imidazol-5-yl)butyl]-N'-[3-(1H-imidazol-5-yl)propyl]carbamimidoyl]benzamide
• CAS: 81282-29-3
• 化学式: C₂₁H₂₇N₇O
• 分子量: 393.492
• InChiKey: HYBIWKJBLMZGNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[N-[4-(1H-imidazol-5-yl)butyl]-N'-[3-(1H-imidazol-5-yl)propyl]carbamimidoyl]benzamide 在 盐酸 作用下， 反应 7.0h， 生成 N-<4-(1H-imidazol-4-yl)butyl>-N'-<3-(1H-imidazol-4-yl)propyl>guanidine
  参考文献：
  名称：

  The histamine H2-receptor agonist impromidine: synthesis and structure activity considerations

  摘要：

  Impromidine (1) is a potent and selective histamine H2 receptor agonist and its structure comprises a strongly basic guanidine group containing two different imidazole-containing side chains. In this paper we report the synthesis of analogues in which both of the side chains and the guanidine group are modified and tested as agonists or antagonists at histamine H2 receptors on guinea pig atrium. A protonated amidine group linked by a chain of three carbon atoms to a tautomeric imidazole ring appears to be an essential feature for agonist activity and it is suggested that the second imidazole-containing side chain in impromidine mainly contributes toward affinity for histamine H2 receptors.

  DOI：

  10.1021/jm00148a007
• 作为产物：
  描述：

  3-(1H-咪唑-4-基)-丙胺 在 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 N-[N-[4-(1H-imidazol-5-yl)butyl]-N'-[3-(1H-imidazol-5-yl)propyl]carbamimidoyl]benzamide
  参考文献：
  名称：

  The histamine H2-receptor agonist impromidine: synthesis and structure activity considerations

  摘要：

  Impromidine (1) is a potent and selective histamine H2 receptor agonist and its structure comprises a strongly basic guanidine group containing two different imidazole-containing side chains. In this paper we report the synthesis of analogues in which both of the side chains and the guanidine group are modified and tested as agonists or antagonists at histamine H2 receptors on guinea pig atrium. A protonated amidine group linked by a chain of three carbon atoms to a tautomeric imidazole ring appears to be an essential feature for agonist activity and it is suggested that the second imidazole-containing side chain in impromidine mainly contributes toward affinity for histamine H2 receptors.

  DOI：

  10.1021/jm00148a007

文献信息

• Process for the preparation of heterocyclylalkyl guanidines; intermediates and their preparation
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0041359A1

  公开（公告）日：1981-12-09

  The invention concerns process for preparing compounds of formula (IX) :- where R1 is attached to a carbon atom in the imidazole moiety and is hydrogen, halogen or alkyl; R2 is hydrogen or a group convertible into hydrogen under acid conditions; R3 is an optionally substituted alkyl group and n is 2, 3 or 4; which comprises reacting a compound of formula (X) :- where n and R1 are as defined with reference to formula (IX), and R2 is a group convertible into hydrogen under acid conditions with a compound of formula (XI) :- where R3 is as defined with reference to formula (IX) and thereafter where desired converting the group R2 into hydrogen. The intermediates of formula (X) novel and are a further aspect of the invention. The process is particularly useful for preparing N-[3-(4-imidazolyl)propyl]- N'-[2-(5-methyl-4-imidazolylmethylthio)ethyl]-guanidine (impromidine).

  本发明涉及式(IX)化合物的制备工艺 其中 R1 连接到咪唑基团中的一个碳原子，是氢、卤素或烷基；R2 是氢或在酸性条件下可转化为氢的基团；R3 是任选取代的烷基，n 是 2、3 或 4；该工艺包括使式 (X) :- 的化合物与式 (IX) :- 的化合物反应，其中 n 和 R1 如参照式 (IX) 所定义，R2 是在酸性条件下可转化为氢的基团。 其中 n 和 R1 如参照式（IX）所定义，R2 是在酸性条件下可转化为氢的基团 与式（XI）化合物反应： - 其中 R3 如参照式（IX）所定义，R2 是在酸性条件下可转化为氢的基团 其中 R3 如式（IX）中所定义，然后根据需要将基团 R2 转化为氢。 式 (X) 的中间体新颖，是本发明的另一个方面。该工艺特别适用于制备 N-[3-(4-咪唑基)丙基]-N'-[2-(5-甲基-4-咪唑基甲硫基)乙基]-胍（impromidine）。
• US4375435A
  申请人：——

  公开号：US4375435A

  公开（公告）日：1983-03-01
• US4443375A
  申请人：——

  公开号：US4443375A

  公开（公告）日：1984-04-17
• The histamine H2-receptor agonist impromidine: synthesis and structure activity considerations
  作者：G. J. Durant、C. R. Ganellin、D. W. Hills、P. D. Miles、M. E. Parsons、E. S. Pepper、G. R. White

  DOI：10.1021/jm00148a007

  日期：1985.10

  Impromidine (1) is a potent and selective histamine H2 receptor agonist and its structure comprises a strongly basic guanidine group containing two different imidazole-containing side chains. In this paper we report the synthesis of analogues in which both of the side chains and the guanidine group are modified and tested as agonists or antagonists at histamine H2 receptors on guinea pig atrium. A protonated amidine group linked by a chain of three carbon atoms to a tautomeric imidazole ring appears to be an essential feature for agonist activity and it is suggested that the second imidazole-containing side chain in impromidine mainly contributes toward affinity for histamine H2 receptors.