N-[3-(2-dimethylaminoethyl)-2-methyl-1H-inden-5-yl]benzo[1,2,5]thiadiazole-4-sulfonamide

• 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: N-[3-(2-dimethylaminoethyl)-2-methyl-1H-inden-5-yl]benzo[1,2,5]thiadiazole-4-sulfonamide
• 英文别名: N-[3-[2-(dimethylamino)ethyl]-2-methyl-1H-inden-5-yl]-2,1,3-benzothiadiazole-4-sulfonamide
• 化学式: C₂₀H₂₂N₄O₂S₂
• 分子量: 414.552
• InChiKey: AIKODYPOOQJRDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-[2-(dimethylamino)ethyl]-2-methyl-1H-inden-5-amine 、 苯并[1,2,5]噻二唑-4-磺酰氯 在 吡啶 作用下， 以65%的产率得到N-[3-(2-dimethylaminoethyl)-2-methyl-1H-inden-5-yl]benzo[1,2,5]thiadiazole-4-sulfonamide
  参考文献：
  名称：

  Indene-Based Scaffolds. 2. An Indole−Indene Switch: Discovery of Novel Indenylsulfonamides as 5-HT₆ Serotonin Receptor Agonists

  摘要：

  Scaffold selection involving an indole-to-indene core change led to the discovery of a series of indenylsulfonamides that act as 5-HT6 serotonin receptor agonists. The variety of the targeted ligands and their synthetic complexity required multistep synthetic approaches. The novel indenylsulfonamides exhibited variable binding affinities for the 5-HT6 receptor, and the in vitro primary binding profiles of the preferred compounds revealed them to be 5-HT6 receptor agonists with K-i values >= 4.5 nM. The structural changes responsible for enhancing the affinities indicated a directing effect modulated by the nature of the indene core, the substitution at the aminoethyl side chain, and especially by the aryl(heteroaryl)sulfonyl group on the indene 5-position. A representative of the family, the N-(inden-5-yl)imidazothiazole-5-sulfonamide (43), exhibited a high affinity and functioned as a potent full agonist for the 5-HT6 receptor (K-i = 4.5 nM, EC50 = 0.9 nM, E-max = 98%).

  DOI：

  10.1021/jm8009469

文献信息

• INDENE DERIVATIVES, THEIR PREPARATION AND USE AS MEDICAMENTS
  申请人：Alcalde-Pais Maria De Las Ermitas

  公开号：US20090163547A1

  公开（公告）日：2009-06-25

  The present invention makes reference to new indene derivatives with general formula (I), as well as to their preparation procedures, their application as medicament and the pharmaceutical compositions containing them. The new compounds of formula (I) show affinity for 5-HT 6 receptors and are, therefore, effective for treating diseases mediated by these receptors.

  本发明涉及一种新的茚烯衍生物，其通式为（I），以及它们的制备方法、作为药物的应用和含有它们的药物组合物。公式（I）的新化合物显示出对5-HT6受体的亲和力，因此对于治疗由这些受体介导的疾病是有效的。
• Combination of at least two 5-HT6-Ligands
  申请人：Laboratorios del Dr. Esteve S.A.

  公开号：EP2020230A1

  公开（公告）日：2009-02-04

  The present invention relates to a Combination of at least two 5HT6- Ligands of which one is a partial or agonist while the other is a full antagonist or an inverse agonist, a medicament comprising this comination, the use of the combiantion in the manufacture of a medicament for the treatment of memory disorders ADHD, and methods of treatment using the combination or its members.

  本发明涉及至少两种5HT6-配体（其中一种为部分或激动剂，另一种为完全拮抗剂或反向激动剂）的组合物、包含该组合物的药物、使用该组合物制造治疗记忆障碍多动症的药物，以及使用该组合物或其成员进行治疗的方法。
• Combination of at least two 5HT6-Ligands
  申请人：Codony-Soler Xavier

  公开号：US20090264457A1

  公开（公告）日：2009-10-22

  The present invention relates to a Combination of at least two 5HT6-Ligands of which one is a partial or agonist while the other is a full antagonist or an inverse agonist, a medicament comprising this comination, the use of the combiantion in the manufacture of a medicament for the treatment of memory disorders ADHD, and methods of treatment using the combination or its members.
• US8217041B2
  申请人：——

  公开号：US8217041B2

  公开（公告）日：2012-07-10
• Indene-Based Scaffolds. 2. An Indole−Indene Switch: Discovery of Novel Indenylsulfonamides as 5-HT₆ Serotonin Receptor Agonists
  作者：Ermitas Alcalde、Neus Mesquida、Sara López-Pérez、Jordi Frigola、Ramon Mercè

  DOI：10.1021/jm8009469

  日期：2009.2.12

  Scaffold selection involving an indole-to-indene core change led to the discovery of a series of indenylsulfonamides that act as 5-HT6 serotonin receptor agonists. The variety of the targeted ligands and their synthetic complexity required multistep synthetic approaches. The novel indenylsulfonamides exhibited variable binding affinities for the 5-HT6 receptor, and the in vitro primary binding profiles of the preferred compounds revealed them to be 5-HT6 receptor agonists with K-i values >= 4.5 nM. The structural changes responsible for enhancing the affinities indicated a directing effect modulated by the nature of the indene core, the substitution at the aminoethyl side chain, and especially by the aryl(heteroaryl)sulfonyl group on the indene 5-position. A representative of the family, the N-(inden-5-yl)imidazothiazole-5-sulfonamide (43), exhibited a high affinity and functioned as a potent full agonist for the 5-HT6 receptor (K-i = 4.5 nM, EC50 = 0.9 nM, E-max = 98%).