5-benzyloxy-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole | 57477-35-7

• 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: 5-benzyloxy-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
• 英文别名: 5-benzyloxy-3-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-indole；5-Phenylmethoxy-3-[1,2,3,6-tetrahydro-1-(phenylmethyl) 4-pyridinyl]-1H-indole；5-Phenylmethoxy-3-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]-1H-indole；3-(1-benzyl-3,6-dihydro-2H-pyridin-4-yl)-5-phenylmethoxy-1H-indole
• CAS: 57477-35-7
• 化学式: C₂₇H₂₆N₂O
• 分子量: 394.516
• InChiKey: OOVSWIUSPKLJQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  5-benzyloxy-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole 生成 3-piperidin-4-yl-1H-indol-5-ol;hydrochloride
  参考文献：
  名称：

  FRIDERICHS E.; BACK W.; MUTSCHLER E., ARCH. PHARM. , 1975, 308, NO 9, 663-675

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄基哌啶酮 、 5-苄氧基吲哚 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以97%的产率得到5-benzyloxy-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
  参考文献：
  名称：

  3-（四氢吡啶基）吲哚

  摘要：

  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。

  DOI：

  10.1016/0040-4020(96)00553-4

文献信息

• Compounds and methods
  申请人：SmithKline Beecham Corporation

  公开号：US06476028B1

  公开（公告）日：2002-11-05

  A method of treating a CCR5-mediated disease state in mammals which comprises administering to a mammal in need of such treatment, an effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof.

  在哺乳动物中治疗CCR5介导的疾病状态的方法，包括向需要此类治疗的哺乳动物施用公式(I)的化合物或其药用盐的有效量。
• 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.
• US6476028B1
  申请人：——

  公开号：US6476028B1

  公开（公告）日：2002-11-05
• 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。
• FRIDERICHS E.; BACK W.; MUTSCHLER E., ARCH. PHARM. <APBD-AJ>, 1975, 308, NO 9, 663-675
  作者：FRIDERICHS E.、 BACK W.、 MUTSCHLER E.

  DOI：——

  日期：——