2-(2-methyl-5-nitro-1H-inden-3-yl)-1-(pyrrolidin-1-yl)ethanone | 936573-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-(2-methyl-5-nitro-1H-inden-3-yl)-1-(pyrrolidin-1-yl)ethanone
• 英文别名: 1-[(2-methyl-5-nitro-1H-inden-3-yl)acetyl]pyrrolidine；2-(2-Methyl-6-nitro-3H-inden-1-yl)-1-pyrrolidin-1-ylethanone
• CAS: 936573-32-9
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: IAAWAEQRBKTCSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-5-nitro-1H-inden-3-yl)-1-(pyrrolidin-1-yl)ethanone 在 alane N,N-dimethylethylamine complex 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 生成 1-[2-(2-Methyl-6-nitro-3H-inden-1-yl)ethyl]pyrrolidine
  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
• 作为产物：
  描述：

  2-methyl-6-nitro-2,3-dihydro-1H-inden-1-one 在 磺酰氯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-(2-methyl-5-nitro-1H-inden-3-yl)-1-(pyrrolidin-1-yl)ethanone
  参考文献：
  名称：

  多功能茚的合成方法。

  摘要：

  具有至少两个不同官能团的多功能茚的合成尚未得到广泛探索。在具有两个不同官能团的 3,5-二取代茚（例如 [3-（氨基乙基）茚-5-基）] 胺的合理合成路线中，合理的途径涉及（5-硝基-3-茚基）乙酰胺作为关键中间体。虽然可以应用几种多步合成方法来获得这些高级中间体，但我们在本文中描述了它们通过 5-硝基茚满-1-酮与 N,N-二取代乙酰胺的锂盐之间的羟醛型反应制备，然后立即用酸。这种经典的缩合过程虽然具有明显的直接性，但既不简单也不平凡，它允许有效地进入各种基于茚的分子模块，

  DOI：

  10.3762/bjoc.7.204

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。
• Indene derivatives, their preparation and use as medicaments
  申请人：LABORATORIOS DEL DR. ESTEVE, S.A.

  公开号：EP2202222A2

  公开（公告）日：2010-06-30

  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-HT6 receptors and are, therefore, effective for treating diseases mediated by these receptors.

  本发明涉及通式（I）的新茚衍生物，以及它们的制备程序、作为药物的应用和含有它们的药物组合物。式 I 的新化合物显示出对 5-HT6 受体的亲和力，因此可有效治疗由这些受体介导的疾病。
• 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
• [EN] INDENE DERIVATIVES, THEIR PREPARATION AND USE AS MEDICAMENTS<br/>[FR] DERIVES D'INDENE, LEUR PREPARATION ET LEUR UTILISATION EN TANT QUE MEDICAMENTS
  申请人：ESTEVE LABOR DR

  公开号：WO2007054257A2

  公开（公告）日：2007-05-18

  [EN] 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-HT₆ receptors and are, therefore, effective for treating diseases mediated by these receptors.
  [FR] La présente invention concerne des nouveaux dérivés d'indène de formule générale (I), de même que des procédures pour leur préparation, leur application en tant que médicament et les compositions pharmaceutiques qui les contiennent. Les nouveaux composés de formule (I) présentent une affinité pour les récepteurs de la 5-HT₆ et ils sont donc efficaces pour le traitement des maladies induites par ces récepteurs.