benzenesulfonic acid 2-(1-benzenesulfonyl-5-methoxy-1H-indol-3-yl)ethyl ester | 297751-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzenesulfonic acid 2-(1-benzenesulfonyl-5-methoxy-1H-indol-3-yl)ethyl ester
• 英文别名: benzenesulphonic acid 2-(1-benzenesulphonyl-5-methoxy-1H-indol-3-yl)ethyl ester；2-[1-(benzenesulfonyl)-5-methoxyindol-3-yl]ethyl benzenesulfonate
• CAS: 297751-52-1
• 化学式: C₂₃H₂₁NO₆S₂
• 分子量: 471.555
• InChiKey: NIGHGROSKZDJLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 benzenesulfonic acid 2-(1-benzenesulfonyl-5-methoxy-1H-indol-3-yl)ethyl ester 在 potassium carbonate 作用下， 以 异丙醇 为溶剂， 生成 1-benzenesulfonyl-5-methoxy-3-[(2-pyrrolidin-1-yl)ethyl]-1H-indole oxalate
  参考文献：
  名称：

  Indole and indoline derivatives as 5-HT6 selective ligands

  摘要：

  揭示了三类吲哚和吲哚啉衍生物作为选择性结合到5-HT6受体的配体，因此在治疗或预防中枢神经系统疾病方面具有价值，包括阿尔茨海默病、帕金森病、精神分裂症、抑郁症和焦虑症。其中一类称为1-取代-4-(&ohgr;-N,N-二烷基氨基烷基)吲哚，被称为新型化合物。

  公开号：

  US06187805B1
• 作为产物：
  描述：

  5-甲氧基吲哚-3-乙醇 、 苯磺酰氯 在 四丁基硫酸氢铵 Brine 、 Sodium sulfate-III 、 silica gel 、 ethyl acetate n-hexane 作用下， 以 sodium hydroxide 、 二氯甲烷 为溶剂， 反应 0.42h， 以to afford 0.095 g (37%) of 2-(1-benzenesulphonyl-5-methoxy-1H-indol-3-yl)ethanol and 0.191 g (52%) of the title compound的产率得到2-(1-benzenesulfonyl-5-methoxy-1H-indol-3-yl)ethanol
  参考文献：
  名称：

  Indole and indoline derivatives as 5-HT6 selective ligands

  摘要：

  公开了三类吲哚和吲哚啉衍生物作为选择性5-HT6受体配体，因此对于治疗或预防中枢神经系统疾病，包括阿尔茨海默病、帕金森病、精神分裂症、抑郁症和焦虑症具有价值。其中一类为1-取代-4-(&ohgr;-N,N-二烷基-氨基烷基)吲哚，被认为是新型化合物。

  公开号：

  US06187805B1

文献信息

• US6187805B1
  申请人：——

  公开号：US6187805B1

  公开（公告）日：2001-02-13
• <i>N</i>-Arylsulfonylindole Derivatives as Serotonin 5-HT₆ Receptor Ligands
  作者：Michael G. N. Russell、Robert J. Baker、Laura Barden、Margaret S. Beer、Linda Bristow、Howard B. Broughton、Michael Knowles、George McAllister、Smita Patel、José L. Castro

  DOI：10.1021/jm010943m

  日期：2001.11.1

  A series of N-1-arylsulfonyltryptamines were found to be potent ligands of the human serotonin 5-HT6 receptor with the 5-methoxy-1-benzenesulfonyl analogue (19) having the highest affinity. Additionally, it was discovered that a group such as 3-(3-methoxybenzyl)-1,2,4-oxadiazol-5-yI in the 2-position of the indole ring (43) can replace the arylsulfonyl substituent in the 1-position with no loss of affinity. This suggested that the binding conformation of the aminoethyl side chain at this receptor was toward the 4-position of the indole ring and was supported by the fact that the 4-(aminoethyl)indoles (45) also displayed high affinity, as did the conformationally rigid 1,3,4,5-tetrahydrobenz[c,d]indole (49). Molecular modeling showed that 19, 43, and 45 all had low-energy conformers that overlaid well onto 49. Both 19 and 49 had good selectivity over other serotonin receptors tested, with 49 also showing excellent selectivity over all dopamine receptors. In a functional adenylate cyclase stimulation assay, 19 and 49 had no agonist activity, whereas 45 behaved as a partial agonist. Finally, it was shown that 19 had good activity in the 5-HT2A centrally mediated mescaline-induced head twitch assay, which implies that it is brain-penetrant.
• Indole and indoline derivatives as 5-HT6 selective ligands
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US06187805B1

  公开（公告）日：2001-02-13

  Three classes of indole and indoline derivatives are disclosed as ligands selective for the 5-HT6 receptors, and hence of value in the treatment or prevention of CNS disorders, including Alzheimer's disease, Parkinson's disease, schizophrenia, depression and anxiety. A particular class, 1-substituted-4-(&ohgr;-N,N-dialkyl-aminoalkyl)indoles, are claimed as novel compounds.

  揭示了三类吲哚和吲哚啉衍生物作为选择性结合到5-HT6受体的配体，因此在治疗或预防中枢神经系统疾病方面具有价值，包括阿尔茨海默病、帕金森病、精神分裂症、抑郁症和焦虑症。其中一类称为1-取代-4-(&ohgr;-N,N-二烷基氨基烷基)吲哚，被称为新型化合物。