6-methoxy-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole | 52157-77-4

• 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: 6-methoxy-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
• 英文别名: 3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-6-methoxy-1H-indole；3-<1'-Benzyl-1',2',3',6'-tetrahydro-pyridyl-(4')>-6-methoxy-indol；3-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-6-methoxy-indole；3-(1'-benzyl-1',2',3',6'-tetrahydro-4'-pyridyl)-6-methoxy-indole；3-(1-benzyl-3,6-dihydro-2H-pyridin-4-yl)-6-methoxy-1H-indole
• CAS: 52157-77-4
• 化学式: C₂₁H₂₂N₂O
• 分子量: 318.418
• InChiKey: RNKJUDZEVXCJQD-UHFFFAOYSA-N

物化性质

• 沸点：
  510.9±50.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methoxy-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole 在 钯 氢气 作用下， 以 甲醇 为溶剂， 生成 6-Methoxy-3-(4'-piperidyl)-indol
  参考文献：
  名称：

  Omega-[4-(3"-indolyl)-piperidino]-alkyl-arylketones as nevroleptics

  摘要：

  新型[4'-(3"-吲哚基)-哌啶基]-烷基芳基酮的化学式为##SPC1## 其中R从由氢和1至5个碳原子的烷氧基组成的基团中选择，R.sub.1和R.sub.2分别从由氢和1至5个碳原子的烷基组成的基团中选择，n为2或3，X从由氢、氟、氯和溴组成的基团中选择，以及其无毒、药用可接受的酸盐，具有中枢神经系统抑制活性。

  公开号：

  US03947578A1
• 作为产物：
  描述：

  1-benzyl-4-(6'-methoxy-3'-indolyl)-pyridinium bromide 在 sodium borohydrid 作用下， 以 甲醇 、 水 为溶剂， 生成 6-methoxy-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
  参考文献：
  名称：

  Omega-[4-(3"-indolyl)-piperidino]-alkyl-arylketones as nevroleptics

  摘要：

  新型[4'-(3"-吲哚基)-哌啶基]-烷基芳基酮的化学式为##SPC1## 其中R从由氢和1至5个碳原子的烷氧基组成的基团中选择，R.sub.1和R.sub.2分别从由氢和1至5个碳原子的烷基组成的基团中选择，n为2或3，X从由氢、氟、氯和溴组成的基团中选择，以及其无毒、药用可接受的酸盐，具有中枢神经系统抑制活性。

  公开号：

  US03947578A1

文献信息

• 3-(Tetrahydropyridinyl)indoles
  作者：Parviz Gharagozloo、Masao Miyauchi、Nigel J.M. Birdsall

  DOI：10.1016/0040-4020(96)00553-4

  日期：1996.7

  Substituted indoles have been condensed with N-benzyl-4-piperidone to give 3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles. Under basic conditions, 5-, 6-, and 7- (but not 4-) substituted indoles give reasonable yields of the product. For condensation with 4-substituted indoles, acidic conditions and the presence of at least a 3-fold excess of N-benzyl-4-piperidone are beneficial. Under basic

  取代的吲哚已经与N-苄基-4-哌啶酮缩合，得到3-（1-苄基-1,2,3,6-四氢吡啶-4-基）-1 H-吲哚。在碱性条件下，用5-，6-和7-（但不是4-）取代的吲哚可得到合理的产物收率。为了与4-取代的吲哚缩合，酸性条件和至少3-倍过量的N-苄基-4-哌啶酮的存在是有利的。在碱性条件下，取决于N-取代基的性质，吲哚与N-取代-3-哌啶酮的缩合是高度区域选择性的，具有区域选择性。4-取代的吲哚不与N反应在碱性条件下被取代的-3-哌啶酮，但在酸性条件下得到单一产物。
• Multitarget Derivatives of D2AAK1 as Potential Antipsychotics: The Effect of Substitution in the Indole Moiety
  作者：Magda Kondej、Tomasz M. Wróbel、Katarzyna M. Targowska‐Duda、Antón Leandro Martínez、Oliwia Koszła、Piotr Stępnicki、Agata Zięba、Alba Paz、Olga Wronikowska‐Denysiuk、Maria I. Loza、Marián Castro、Agnieszka A. Kaczor

  DOI：10.1002/cmdc.202200238

  日期：2022.8.3

  17 derivatives of the virtual hit D2AAK1 were designed, synthesized and evaluated for their affinity for D2, 5-HT1A and 5-HT2A receptors. Two multitarget compounds were chosen for in vivo studies, and their antipsychotic activity was evaluated in rodents. Structure-activity relationship analysis revealed that substitutions at positions C4 and C5 of the indole moiety were most favourable for the multi-receptor

  设计、合成了虚拟命中 D2AAK1 的17 种衍生物，并评估了它们对 D 2、5-HT 1A和 5-HT 2A受体的亲和力。选择了两种多靶点化合物进行体内研究，并在啮齿动物中评估了它们的抗精神病活性。构效关系分析表明，吲哚部分 C4 和 C5 位的取代最有利于这些分子的多受体谱。
• Substituted Pentacyclic Carbazolones as Novel Muscarinic Allosteric Agents:  Synthesis and Structure−Affinity and Cooperativity Relationships
  作者：Parviz Gharagozloo、Sebastian Lazareno、Masao Miyauchi、Angela Popham、Nigel J. M. Birdsall

  DOI：10.1021/jm010946z

  日期：2002.3.1

  Two series of pentacyclic carbazolones, 22 and 23, have been synthesized utilizing a facile intramolecular Diels-Alder reaction and are allosteric modulators at muscarinic acetylcholine receptors. Their affinities and cooperativities with acetylcholine and the antagonist N-methylscopolamine (NMS) at M-1-M-4 receptors have been analyzed and compared. All of the synthesized compounds are negatively cooperative with acetylcholine. In contrast, the majority of the compounds exhibit positive cooperativity with NMS, particularly at M-2 and M-4 receptors. The subtype selectivity, in terms of affinity, was in general M-2 > M-1 > M-4 > M-3. The largest increases in affinity produced by a single substitution of the core structure were given by the 1-OMe (22b) and 1-Cl (22d) derivatives. The position of the N in the ring did not appear to be important for binding affinity or cooperativity. Two compounds 22y and 23i, both trisubstituted analogues, were the most potent compounds synthesized, with dissociation constants of 30-100 nM for the M-2 NMS-liganded and unliganded receptor, respectively. The results indicate that the allosteric site, like the primary binding site, is capable of high-affinity interactions with molecules of relatively low molecular weight.
• US3947578A
  申请人：——

  公开号：US3947578A

  公开（公告）日：1976-03-30