2-methyl-N-naphth-1-yl-3-oxoindane-5-sulfonamide | 936573-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-methyl-N-naphth-1-yl-3-oxoindane-5-sulfonamide
• 英文别名: N-(naphthalene-1-yl)-2-methyl-3-oxoindano-5-sulfonamide；2-methyl-N-naphthalen-1-yl-3-oxo-1,2-dihydroindene-5-sulfonamide
• CAS: 936573-79-4
• 化学式: C₂₀H₁₇NO₃S
• 分子量: 351.426
• InChiKey: CSQPSODCVMICSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-N-naphth-1-yl-3-oxoindane-5-sulfonamide 在 lithium hexamethyldisilazane 、 盐酸 、 甲醇 、 水 、 sodium 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 {2-methyl-5-[(1-naphthylamino)sulfonyl]-1H-inden-3-yl}acetic acid
  参考文献：
  名称：

  WO2007/54257

  摘要：

  公开号：
• 作为产物：
  描述：

  2-methyl-3-oxoindane-5-sulfonyl chloride 、 1-萘胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以76%的产率得到2-methyl-N-naphth-1-yl-3-oxoindane-5-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。
• 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。
• 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.
• 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%).