(S)-3-(1-methylpyrrolidin-2-ylmethyl)-1H-indole | 863024-27-5

• 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: (S)-3-(1-methylpyrrolidin-2-ylmethyl)-1H-indole
• 英文别名: 3-((S)-1-Methyl-pyrrolidin-2-ylmethyl)-1H-indole; hydrochloride；3-[[(2S)-1-methylpyrrolidin-2-yl]methyl]-1H-indole
• CAS: 863024-27-5
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: HCTCDEAMCNSARD-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-3-(1-methylpyrrolidin-2-ylmethyl)-1H-indole 、 2-溴苯磺酰氯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 1-(2-Bromo-benzenesulfonyl)-3-((S)-1-methyl-pyrrolidin-2-ylmethyl)-1H-indole
  参考文献：
  名称：

  Conformationally constrained N1-arylsulfonyltryptamine derivatives as 5-HT6 receptor antagonists

  摘要：

  Several series of conformationally constrained N-1-arylsulfonyltryptamine derivatives were prepared and tested for 5-HT6 receptor binding affinity and ability to modulate cAMP production in a cyclase assay. The 3-piperidin-3-yl-, 3-(1-methylpyrrolidin-2-ylmethyl)-, and 3-pyrrolidin-3-yl-1H-indole arrays (8-13) appear to be able to adopt a conformation that allows high affinity 5-HT6 receptor binding, while the beta-carboline array 14 binds with a significantly weaker (10- to 100-fold) affinity. N-1-Benzenesulfonyl-3-piperidin-3-yl-1H-indole 9a is a high affinity full agonist with EC50 = 24 nM. Several of the N-1-arylsulfonyl-3-(1-methylpyrrolidin-2-ylmethyl)-1H-indole derivatives behave as very potent antagonists ((S)- 11r, (S)- 11t; IC50 = 0.8, 1.0 nM). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.028
• 作为产物：
  描述：

  吲哚 在 lithium aluminium tetrahydride 、 锂硼氢 、 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-3-(1-methylpyrrolidin-2-ylmethyl)-1H-indole
  参考文献：
  名称：

  Interaction of chiral MS-245 analogs at h5-HT6 receptors

  摘要：

  Optically active pyrrolidinylmethylindole analogs related in structure to the benzenesulfonyltryptamine 5-HT(6) receptor antagonist MS-245 were evaluated and their R-isomers were found to bind with affinity higher than their S-enantiomers.

  DOI：

  10.1016/j.bmcl.2005.05.092

文献信息

• Interaction of chiral MS-245 analogs at h5-HT6 receptors
  作者：Carmen Abate、Renata Kolanos、Malgorzata Dukat、Vince Setola、Bryan L. Roth、Richard A. Glennon

  DOI：10.1016/j.bmcl.2005.05.092

  日期：2005.8

  Optically active pyrrolidinylmethylindole analogs related in structure to the benzenesulfonyltryptamine 5-HT(6) receptor antagonist MS-245 were evaluated and their R-isomers were found to bind with affinity higher than their S-enantiomers.
• Conformationally constrained N1-arylsulfonyltryptamine derivatives as 5-HT6 receptor antagonists
  作者：Derek C. Cole、William J. Lennox、Joseph R. Stock、John W. Ellingboe、Hossein Mazandarani、Deborah L. Smith、Guoming Zhang、Gregory J. Tawa、Lee E. Schechter

  DOI：10.1016/j.bmcl.2005.07.028

  日期：2005.11

  Several series of conformationally constrained N-1-arylsulfonyltryptamine derivatives were prepared and tested for 5-HT6 receptor binding affinity and ability to modulate cAMP production in a cyclase assay. The 3-piperidin-3-yl-, 3-(1-methylpyrrolidin-2-ylmethyl)-, and 3-pyrrolidin-3-yl-1H-indole arrays (8-13) appear to be able to adopt a conformation that allows high affinity 5-HT6 receptor binding, while the beta-carboline array 14 binds with a significantly weaker (10- to 100-fold) affinity. N-1-Benzenesulfonyl-3-piperidin-3-yl-1H-indole 9a is a high affinity full agonist with EC50 = 24 nM. Several of the N-1-arylsulfonyl-3-(1-methylpyrrolidin-2-ylmethyl)-1H-indole derivatives behave as very potent antagonists ((S)- 11r, (S)- 11t; IC50 = 0.8, 1.0 nM). (c) 2005 Elsevier Ltd. All rights reserved.