indole-3-carboxylic acid methyl imido ester hydrochloride | 74862-25-2

• 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
• 英文名称: indole-3-carboxylic acid methyl imido ester hydrochloride
• 英文别名: methyl imino ester hydrochloride of 3-indolecarboxylic acid；methyl 1H-indole-3-carboxamidate hydrochloride；Methyl (1H-indol-3-yl)imidate hydrochloride；Methyl 1H-indole-3-carboximidoate hydrochloride；methyl 1H-indole-3-carboximidate;hydrochloride
• CAS: 74862-25-2
• 化学式: C₁₀H₁₀N₂O*ClH
• 分子量: 210.663
• InChiKey: NSEKEFFTCYQFER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  indole-3-carboxylic acid methyl imido ester hydrochloride 在 氢氧化钾 作用下， 以 乙醚 为溶剂， 以81%的产率得到indole-3-carboxylic acid methyl imido ester
  参考文献：
  名称：

  唑及其衍生物的合成和性质。32.吲哚羧酸亚氨基酯盐酸盐的合成及部分转化

  摘要：

  DOI：

  10.1007/bf00561348
• 作为产物：
  描述：

  甲醇 、 3-氰基吲哚 在 盐酸 作用下， 反应 24.0h， 生成 indole-3-carboxylic acid methyl imido ester hydrochloride
  参考文献：
  名称：

  Tropane-3-spiro-4'（5'）-咪唑啉衍生的新化合物作为潜在的5-HT3受体拮抗剂的合成，结构，构象，生化和药理研究

  摘要：

  通过1H和13C NMR光谱合成和研究了一系列tropane-3-spiro-4'（5'）-咪唑啉，并研究了2'-（1H-吲哚-3-基）tropane-3-spiro的晶体结构。通过X射线衍射测定了-4'（5'）-咪唑啉盐酸盐5（6）f。在CD3OD溶液中，化合物5（6）af显示相同的优选构象。吡咯烷环和哌啶环分别具有在N8处变平的外壳构象和在N8处折叠且在C3处变平的扭曲椅构象，且N取代基相对于哌啶环处于赤道位置。该构象类似于在固态下对化合物5（6）f观察到的构象。通过对合成化合物的结合研究，化合物5（6）d证明能够有效地将[3H] GR65630与牛脑后膜的结合置换到与MDL 72222相当的程度。在von Bezold-Jarisch反射中，化合物5（6）d与甲氧氯普胺。因此，咪唑啉环很可能可以为5-HT3拮抗剂中的羰基提供有用的生物等位替代。

  DOI：

  10.1002/jps.2600840123

文献信息

• Synthesis of 2′-Arylazabicyclo-3-spiro-4′(5′)-imidazolines
  作者：Brendan Whelan、Isabel Iriepa、Enrique Galvez

  DOI：10.1055/s-1994-25584

  日期：——

  A method is described for the synthesis of a series of 2′-aryl-3-azabicyclospiro-4′ (5′)-imidazolines via the reaction of azabicyclic 1,2-diamines with aryl imidate salts. Competing reactions in the synthesis of the diamines such as the reduction of amino nitriles with LiAlH4 lead to some anomalous products. In the Pinner synthesis, unstable pyridine-type imidates were stabilized as their N-oxide derivatives.

  本文描述了一种通过氮杂双环1,2-二胺与芳基亚氨盐反应合成一系列2′-芳基-3-氮杂双环螺-4′(5′)-咪唑啉的方法。在二胺的合成过程中，如氨基腈与LiAlH4的还原反应等竞争性反应导致一些异常产物的生成。在Pinner合成法中，不稳定的吡啶型亚氨盐被其N-氧化衍生物所稳定化。
• Synthesis of indole oxazolines, potent 5-HT3 antagonists
  作者：Christopher J Swain、Clare Kueen、Raymond Baker

  DOI：10.1016/s0040-4039(00)97385-4

  日期：1990.1
• Novel 5-HT3 antagonists: indol-3-ylspiro(azabicycloalkane-3,5'(4'H)oxazoles)
  作者：C. J. Swain、R. Baker、C. Kneen、R. Herbert、J. Moseley、J. Saunders、E. M. Seward、G. I. Stevenson、M. Beer

  DOI：10.1021/jm00084a007

  日期：1992.3

  The synthesis and biochemical evaluation of a series of spirofused indole oxazoline 5-HT3 antagonists is described in which the oxazoline ring acts as a bioisosteric replacement for esters and amides. The effect of substitution about the indole ring has shown the steric limitations of the aromatic binding site. Incorporation of a variety of azabicyclic systems within the rigid spirofused framework has allowed the definition of a binding model which incorporates a number of known antagonists and agonists. In this model steric constraints limit substitution around the indole ring although there is some bulk tolerance at the 1- and 2-positions. The importance of constraining the basic nitrogen within an azabicyclic system is underlined by comparison with the monocyclic piperidine. The highest affinity was observed for those compounds in which the basic nitrogen occupies a bridgehead position, the most potent analogue in this group being the azabicyclic [3.3.1] system (pIC50 = 8.95), suggesting lipophilic interactions may play a role in increasing affinity. A suggested model for agonist binding is included in which the basic nitrogens are superimposed and the 5-hydroxyl group of 5-HT is superimposed on the H-bond-accepting atom of the heterocyclic linking group.
• Synthesis and properties of furan derivatives. 3. Synthesis of 1,2-disubstituted ?2-imidazolines containing furfuryl and tetrahydrofurfuryl groups
  作者：R. A. Karakhanov、V. I. Kelarev、A. S. Remizov、Yu. N. Polivin、D. Oietaio

  DOI：10.1007/bf00529570

  日期：1992.10
• Swain, Christopher J.; Kneen, Clare; Herbert, Richard, Journal of the Chemical Society. Perkin transactions I, 1990, # 11, p. 3183 - 3186
  作者：Swain, Christopher J.、Kneen, Clare、Herbert, Richard、Baker, Raymond

  DOI：——

  日期：——