(3,3-dimethyl-6-nitro-2,3-dihydro-1H-inden-1-ylidene)acetonitrile | 1119518-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (3,3-dimethyl-6-nitro-2,3-dihydro-1H-inden-1-ylidene)acetonitrile
• 英文别名: 2-(3,3-dimethyl-6-nitro-2H-inden-1-ylidene)acetonitrile
• CAS: 1119518-81-8
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: OVQBWCYQZJINJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,3-dimethyl-6-nitro-1-indanone 、 乙腈 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (1,1-dimethyl-5-nitro-1H-inden-3-yl)acetonitrile 、 (3,3-dimethyl-6-nitro-2,3-dihydro-1H-inden-1-ylidene)acetonitrile
  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