4-[2-(2-甲基吲哚-1-基)乙基]吗啉 | 103608-37-3

• 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: 4-[2-(2-甲基吲哚-1-基)乙基]吗啉
• 英文名称: 2-methyl-1-<2-(4-morpholinyl)ethyl>-1H-indole
• 英文别名: 4-(2-(2-methyl-1H-indol-1-yl)ethyl)morpholine；2-methyl-1-[2-(4-morpholinyl)ethyl]-1H-indole；N-(2-(N-morpholino)ethyl)-2-methylindole；1H-Indole, 2-methyl-1-[2-(4-morpholinyl)ethyl]-；4-[2-(2-methylindol-1-yl)ethyl]morpholine
• CAS: 103608-37-3
• 化学式: C₁₅H₂₀N₂O
• 分子量: 244.337
• InChiKey: ASRCZIZEMMGLDI-UHFFFAOYSA-N

物化性质

• 熔点：
  63-65 °C(Solv: heptane (142-82-5))
• 沸点：
  404.2±35.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  17.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[2-(2-甲基吲哚-1-基)乙基]吗啉 生成 2-methyl-1-<2-(4-morpholinyl)ethyl>-1H-indole-3-carboxaldehyde
  参考文献：
  名称：

  BELL, MALCOLM R.

  摘要：

  DOI：
• 作为产物：
  描述：

  N-phenylacetamidine 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium acetate 、 sodium hydride 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-[2-(2-甲基吲哚-1-基)乙基]吗啉
  参考文献：
  名称：

  Synthesis of indoles and quinazolines via additive-controlled selective C–H activation/annulation of N-arylamidines and sulfoxonium ylides

  摘要：

  通过改变添加剂，通过精确控制C-H活化/环化实现了对吲哚和喹唑啉的选择性合成。

  DOI：

  10.1039/c9cc01146c

文献信息

• Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor
  作者：Dalel El-Marrouki、Sabrina Touchet、Abderrahmen Abdelli、Hédi M’Rabet、Mohamed Lotfi Efrit、Philippe C Gros

  DOI：10.3762/bjoc.16.144

  日期：——

  convergent strategy is reported for the construction of nitrogen-containing heterocycles from common substrates: 1,4-diketones and primary amines. Indeed, by just varying the substrates, the substituents, or the heating mode, it is possible to selectively synthesize indole, indolone (1,5,6,7-tetrahydroindol-4-one), or cinnoline (5,6,7,8-tetrahydrocinnoline) derivatives in moderate to excellent yields.

  据报道，一种聚合策略可用于从常见底物上构建含氮杂环：1,4-二酮和伯胺。实际上，只要改变底物，取代基或加热方式，就可以选择性地合成吲哚，吲哚酮（1,5,6,7-tetrahydroindol-4-one）或cinnoline（5,6,7， 8-四氢cinnoline）衍生物，产率中等至优异。
• COMPOSITION AND METHODS FOR TREATING GLIOBLASTOMA
  申请人：Stella Nephi

  公开号：US20130197026A1

  公开（公告）日：2013-08-01

  The disclosure provides methods of treating glioblastoma, methods of screening for compounds that treat glioblastoma, and pharmaceutical compositions useful the treatment of glioblastoma.

  该披露提供了治疗胶质母细胞瘤的方法，筛选治疗胶质母细胞瘤的化合物的方法，以及用于治疗胶质母细胞瘤的药物组合物。
• 3-Arylcarbonyl-1-aminoalkyl-1H-indole containing antiglaucoma compositions
  申请人：STERLING WINTHROP INC.

  公开号：EP0445781A1

  公开（公告）日：1991-09-11

  Antiglaucoma compositions containing 3-arylcarbonyl-1-aminoalkyl-1H-indoles, as the active component thereof, and a method of use thereof in the treatment of glaucoma. Also included are novel 3-arylcarbonyl-1-aminoalkyl-1H-indoles.

  含有作为其活性成分的 3-芳基羰基-1-氨基烷基-1H-吲哚的抗青光眼组合物及其治疗青光眼的使用方法。此外，还包括新型 3-芳基羰基-1-氨基烷基-1H-吲哚。
• Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics
  作者：Michael A. Eissenstat、Malcolm R. Bell、Thomas E. D'Ambra、E. John Alexander、Sol J. Daum、James H. Ackerman、Monte D. Gruett、Virendra Kumar、Kimberly G. Estep

  DOI：10.1021/jm00016a013

  日期：1995.8

  Aminoalkylindoles (AAIs) are a novel series of cannabinoid receptor ligands. In this report we disclose the structural features of AAIs which are important for binding to this receptor as measured by inhibition of binding of [H-3]Win 55212-2 (5). Functional activity in the mouse vas deferens is also noted and used to distinguish agonists from potential antagonists. The key structural features for potent cannabinoid activity in this series are a bicyclic (naphthyl) substituent at the 3-position, a small (II) substituent at the 2-position, and an aminoethyl (morpholinoethyl) substituent at the 1-position. A 6-bromo analog, Win 54461 (31), has been identified as a potential cannabinoid receptor antagonist. Modeling experiments were done to develop a pharmacophore and also to compare AAI structures with those of classical cannabinoids. The fact that the cannabinoid AAIs arose out of work on a series of cyclooxygenase inhibitors makes sense now that an endogenous cannabinoid ligand has been identified which is a derivative of arachidonic acid. Because of their unique structures and physical properties, AAIs provide useful tools to study the structure and function of the cannabinoid receptor(s).
• Antinociceptive (aminoalkyl)indoles
  作者：Malcolm R. Bell、Thomas E. D'Ambra、Virendra Kumar、Michael A. Eissenstat、John L. Herrmann、Joseph R. Wetzel、David Rosi、Richard E. Philion、Sol J. Daum

  DOI：10.1021/jm00107a034

  日期：1991.3

  The (aminoalkyl)indole (AAI) derivative pravadoline (1a) inhibited prostaglandin (PG) synthesis in mouse brain microsomes in vitro and ex vivo and exhibited antinociceptive activity in several rodent assays. In vitro structure-activity relationship studies of this new class of PG synthesis inhibitors revealed a correspondence in three respects to those reported for the arylacetic acids: (1) ''alpha-methylation'' caused an increase in PG inhibitory potency, (2) the (R)-alpha-methyl isomer was more active than the S isomer, (3) the hypothesized aroyl group conformation of the 2-methyl derivatives corresponded to the proposed and reported ''active'' conformations of the aroyl and related aromatic acetic acid derivatives. The H-1 NMR chemical shift of the C-4 hydrogen of pravadoline in comparison to the deshielding seen with 50, which lacks a substituent at C-2, suggested that the carbonyl group of pravadoline is located near C-2 but is located near C-4 in 50. Associated with this conformational change of the carbonyl group of 1a is a diminution of PG synthetase inhibitory activity. The results of UV and difference nuclear Overhauser studies of the two compounds were consistent with these conformational assignments. The low eudismic ratios of the alpha-methyl derivatives and the observation that the side chain may be extended by three methylene groups without significant loss of PG inhibitory potency suggests that this class of inhibitors bound less strongly and less selectively to the active site of PG synthetase than do the arylacetic acids. Two AAIs, 1a and 30, were found to be metabolized to the corresponding acetic acid derivatives, both of which inhibited PG synthesis. An exception to the observation that the antinociceptive activity of the AAIs was associated with PG synthetase inhibitory activity was the 1-naphthoyl derivative 67 since neither it nor its acetic acid metabolite 74 inhibited PG synthesis. Yet 67 was antinociceptive in four different rodent assays. This naphthoyl derivative, like opioids, also inhibited electrically stimulated contractions in the mouse vas deferens (MVD) preparation. Unlike opioids, however, the inhibition was not antagonized by naloxone. A subseries of AAIs was identified, of which 67 was prototypic. These compounds lacked PG synthetase inhibitory activity, but their inhibitory potency in MVD preparations correlated roughly with their antinociceptive potency in vivo. Pravadoline was also inhibitory in the MVD. Its antinociceptive activity, therefore, may be a consequence of both its PG synthetase inhibitory potency and another antinociceptive mechanism, the latter associated with its inhibitory potency in the MVD. The evidence is summarized which suggests that this second antinociceptive mechanism is associated with binding to the recently characterized cannabinoid receptor.