N-(2-[7-(cyclohexylmethyl)-1,6-dihydro-2H-indeno[5,4-b]-furan-8-yl]ethyl)acetamide | 1287785-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: N-(2-[7-(cyclohexylmethyl)-1,6-dihydro-2H-indeno[5,4-b]-furan-8-yl]ethyl)acetamide
• 英文别名: Cifea；N-[2-[7-(cyclohexylmethyl)-2,6-dihydro-1H-cyclopenta[e][1]benzofuran-8-yl]ethyl]acetamide
• CAS: 1287785-08-3
• 化学式: C₂₂H₂₉NO₂
• 分子量: 339.478
• InChiKey: MMMAALHYEKMNHU-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  558.1±39.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2,6,7-四氢-8H-茚并[5,4-b]呋喃-8-酮 在 盐酸 、 palladium 10% on activated carbon 、 氨 、 氢气 、 sodium hydride 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 mineral oil 为溶剂， 反应 151.67h， 生成 N-(2-[7-(cyclohexylmethyl)-1,6-dihydro-2H-indeno[5,4-b]-furan-8-yl]ethyl)acetamide
  参考文献：
  名称：

  1,6-Dihydro-2H-indeno[5,4-b]furan Derivatives: Design, Synthesis, and Pharmacological Characterization of a Novel Class of Highly Potent MT₂-Selective Agonists

  摘要：

  A novel series of 1,6-dihydro-2H-indeno[5,4-b]furan derivatives were designed and synthesized as MT2-selective ligands. This scaffold was identified as a potent mimic of the 5-methoxy indole core of melatonin, and introduction of a cyclohexylmethyl group at the 7-position of this scaffold afforded an MT2-selective ligand 15 (K-i = 0.012 nM) with high MT1/MT2 selectivity (799). Compound 15 was identified as a potent full agonist for the MT2 subtype and exhibited reentrainment effects to a new light/dark cycle in ICR mice at 3-30 mg/kg. This result demonstrated the involvement of the MT2 receptors in chronobiotic activity.

  DOI：

  10.1021/jm200221q

文献信息

• 1,6-Dihydro-2<i>H</i>-indeno[5,4-<i>b</i>]furan Derivatives: Design, Synthesis, and Pharmacological Characterization of a Novel Class of Highly Potent MT₂-Selective Agonists
  作者：Tatsuki Koike、Yasutaka Hoashi、Takafumi Takai、Masaharu Nakayama、Nobuhito Yukuhiro、Takashi Ishikawa、Keisuke Hirai、Osamu Uchikawa

  DOI：10.1021/jm200221q

  日期：2011.5.12

  A novel series of 1,6-dihydro-2H-indeno[5,4-b]furan derivatives were designed and synthesized as MT2-selective ligands. This scaffold was identified as a potent mimic of the 5-methoxy indole core of melatonin, and introduction of a cyclohexylmethyl group at the 7-position of this scaffold afforded an MT2-selective ligand 15 (K-i = 0.012 nM) with high MT1/MT2 selectivity (799). Compound 15 was identified as a potent full agonist for the MT2 subtype and exhibited reentrainment effects to a new light/dark cycle in ICR mice at 3-30 mg/kg. This result demonstrated the involvement of the MT2 receptors in chronobiotic activity.