C-[3-(2-Dimethylamino-ethyl)-1H-indol-5-yl]-N-[4-({[3-(2-dimethylamino-ethyl)-1H-indol-5-ylmethanesulfonyl]-methyl-amino}-methyl)-benzyl]-N-methyl-methanesulfonamide

• 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: C-[3-(2-Dimethylamino-ethyl)-1H-indol-5-yl]-N-[4-({[3-(2-dimethylamino-ethyl)-1H-indol-5-ylmethanesulfonyl]-methyl-amino}-methyl)-benzyl]-N-methyl-methanesulfonamide
• 英文别名: 1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-[[4-[[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methylsulfonyl-methylamino]methyl]phenyl]methyl]-N-methylmethanesulfonamide
• 化学式: C₃₆H₄₈N₆O₄S₂
• 分子量: 692.947
• InChiKey: GICSJGBGXBQUQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  磺马曲坦 、 1,4-对二氯苄 在 sodium hydride 作用下， 生成 C-[3-(2-Dimethylamino-ethyl)-1H-indol-5-yl]-N-[4-({[3-(2-dimethylamino-ethyl)-1H-indol-5-ylmethanesulfonyl]-methyl-amino}-methyl)-benzyl]-N-methyl-methanesulfonamide
  参考文献：
  名称：

  Dimerization of sumatriptan as an efficient way to design a potent, centrally and orally active 5-HT1B agonist

  摘要：

  A new bivalent ligand of formula 3 which results from the covalent coupling of two sumatriptan molecules with a p-xylyl spacer at the level of the sulfonamide nitrogen has been prepared and evaluated as a 5-HT1B/1D receptors agonist. In vitro experiments at 5-HT1B human cloned receptors (Ki = 0.64 nM; EC50 = 0.58 nM) and at the level of the contraction of the New Zealand white rabbit saphenous vein (pD(2) = 6.6) demonstrate the superior potency of dimer 3 as a 5-HT1B receptor agonist when compared to sumatriptan or zolmitriptan. Interestingly enough, the new bivalent agonist 3 was found to induce hypothermia in the guineapig upon oral administration suggesting good oral activity and access to the brain. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00090-0

文献信息

• Dimerization of sumatriptan as an efficient way to design a potent, centrally and orally active 5-HT1B agonist
  作者：Michel Perez、Petrus J. Pauwels、Catherine Fourrier、Philippe Chopin、Jean-Pierre Valentin、Gareth W. John、M. Marien、Serge Halazy

  DOI：10.1016/s0960-894x(98)00090-0

  日期：1998.3

  A new bivalent ligand of formula 3 which results from the covalent coupling of two sumatriptan molecules with a p-xylyl spacer at the level of the sulfonamide nitrogen has been prepared and evaluated as a 5-HT1B/1D receptors agonist. In vitro experiments at 5-HT1B human cloned receptors (Ki = 0.64 nM; EC50 = 0.58 nM) and at the level of the contraction of the New Zealand white rabbit saphenous vein (pD(2) = 6.6) demonstrate the superior potency of dimer 3 as a 5-HT1B receptor agonist when compared to sumatriptan or zolmitriptan. Interestingly enough, the new bivalent agonist 3 was found to induce hypothermia in the guineapig upon oral administration suggesting good oral activity and access to the brain. (C) 1998 Elsevier Science Ltd. All rights reserved.