1-甲基吲哚-3-羧酰胺 | 730237-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-甲基吲哚-3-羧酰胺
• 英文名称: 1-methyl-1H-indole-3-carboxamidine
• 英文别名: 1-methyl-1H-indole-3-carboximidamide；1-methylindole-3-carboximidamide
• CAS: 730237-52-2
• 化学式: C₁₀H₁₁N₃
• mdl: MFCD07776746
• 分子量: 173.217
• InChiKey: JTILKDPVZUCLCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-氰基-1-甲基吲哚 在 盐酸 、 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 1-甲基吲哚-3-羧酰胺
  参考文献：
  名称：

  Novel 5-HT3 antagonists. Indole oxadiazoles

  摘要：

  The synthesis and biochemical evaluation of a series of indole oxadiazole 5-HT3 antagonists are described. The key pharmacophoric elements have been defined as a basic nitrogen, a linking group capable of H-bonding interactions, and an aromatic moiety. The steric limitations of the aromatic binding site have been determined by substitution about the indole ring. Variation of the heterocyclic linking group has shown that while two hydrogen-bonding interactions are possible, only one is essential for high affinity. The environment of the basic nitrogen has been investigated and shown to be optimal when constrained within an azabicyclic system. These results have been incorporated into a proposed binding model for the 5-HT3 antagonist binding site, in which the optimum distance between the aromatic binding site and the basic amine is 8.4-8.9 angstrom and the steric limitations are defined by van der Waals difference mapping.

  DOI：

  10.1021/jm00105a021

文献信息

• Route to 3-Amidino Indoles via Pd(II)-Catalyzed C–H Bond Activation
  作者：Jonas Rydfjord、Bobo Skillinghaug、Peter Brandt、Luke R. Odell、Mats Larhed

  DOI：10.1021/acs.orglett.7b01836

  日期：2017.8.4

  We report a facile synthesis of 3-amidino indoles from indoles and cyanamides. The reaction is Pd(II)-catalyzed and proceeds via C–H bond activation of the indole in its 3-position followed by a 1,2-addition of the resulting indole–palladium σ-complex to a cyanamide, which provides the corresponding amidine. The preference for 4,5-diazafluoren-9-one (DAF) as the ligand is investigated using DFT calculations

  我们报道了从吲哚和氰胺类化合物轻松合成3-ami基吲哚类化合物。该反应是Pd（II）催化的，通过吲哚在其3-位的CH键活化，然后将所得的吲哚-钯σ-络合物1,2-加至氰胺中，从而提供相应的反应。 idine。使用DFT计算研究了4,5-二氮杂芴-9-one（DAF）作为配体的偏好，并提出了合理的反应途径。
• Kelarew W. I., Gasanow S. Sh., Karakhanow R. A., Poliwin Ju. N., Kuatbeko+, Zh. organ. khimii., 28 (1992) N 12, S 2561-2568
  作者：Kelarew W. I., Gasanow S. Sh., Karakhanow R. A., Poliwin Ju. N., Kuatbeko+

  DOI：——

  日期：——
• Novel 5-HT3 antagonists. Indole oxadiazoles
  作者：C. J. Swain、R. Baker、C. Kneen、J. Moseley、J. Saunders、E. M. Seward、G. Stevenson、M. Beer、J. Stanton、K. Watling

  DOI：10.1021/jm00105a021

  日期：1991.1

  The synthesis and biochemical evaluation of a series of indole oxadiazole 5-HT3 antagonists are described. The key pharmacophoric elements have been defined as a basic nitrogen, a linking group capable of H-bonding interactions, and an aromatic moiety. The steric limitations of the aromatic binding site have been determined by substitution about the indole ring. Variation of the heterocyclic linking group has shown that while two hydrogen-bonding interactions are possible, only one is essential for high affinity. The environment of the basic nitrogen has been investigated and shown to be optimal when constrained within an azabicyclic system. These results have been incorporated into a proposed binding model for the 5-HT3 antagonist binding site, in which the optimum distance between the aromatic binding site and the basic amine is 8.4-8.9 angstrom and the steric limitations are defined by van der Waals difference mapping.