N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]cyclobutane carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]cyclobutane carboxamide
• 英文别名: N-[2-(2,7-dimethoxy-9H-fluoren-9-yl)ethyl]cyclobutanecarboxamide
• 化学式: C₂₂H₂₅NO₃
• 分子量: 351.445
• InChiKey: MJXUOIVQCYJAKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,4'-dimethoxy-[1,1'-biphenyl]-2-carboxylic acid methyl ester 在 platinum(IV) oxide 4-二甲氨基吡啶 、 sodium hydroxide 、 氯化亚砜 、 氯仿 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0~79.0 ℃ 、344.74 kPa 条件下， 反应 41.25h， 生成 N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]cyclobutane carboxamide
  参考文献：
  名称：

  Chronobiotic activity of N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]-propanamide. Synthesis and melatonergic pharmacology of fluoren-9-ylethyl amides

  摘要：

  A series of fluoren-9-yl ethyl amides (2) were synthesized and evaluated for human melatonin MT1 and MT2 receptor binding. N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]propanamide (2b) was selected and evaluated in functional assays measuring intrinsic activity at the human MT1 and MT2 receptors and demonstrated full agonism at both receptors. The chronobiotic properties of 2b were demonstrated in both acute and chronic rat models where 2b produced an acute phase advance of 32 min at 1 mg/kg and chronically entrained free-running rats with a mean effective dose of 0.23 mg/kg. Compound 2b is significantly less efficacious than melatonin in constricting human coronary artery. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.002

文献信息

• Ethylamido fluorenes and improved method of making same
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0747345A2

  公开（公告）日：1996-12-11

  Novel substituted fluorene compunds of Formula I are active as melatonergic agents: wherein: X= H, halogen, OH or OZ; Z= C1-6 alkyl; -(CH2)m-CF3 (m=0-2); CD3; or n=1 or 2; and R= C1-6 alkyl, C3-6 cycloalkyl, C2-4 alkenyl, halogen substituted C1-6 alkyl, or C1-6 alkoxy substituted C1-6 alkyl.

  式 I 的新型取代芴化合物具有褪黑激素活性： 其中 X= H、卤素、OH 或 OZ； Z= C1-6 烷基；-(CH2)m-CF3（m=0-2）；CD3；或 n=1 或 2；以及 R= C1-6 烷基、C3-6 环烷基、C2-4 烯基、卤素取代的 C1-6 烷基或 C1-6 烷氧基取代的 C1-6 烷基。
• US5736578A
  申请人：——

  公开号：US5736578A

  公开（公告）日：1998-04-07
• Chronobiotic activity of N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]-propanamide. Synthesis and melatonergic pharmacology of fluoren-9-ylethyl amides
  作者：James R. Epperson、Marc A. Bruce、John D. Catt、Jeffrey A. Deskus、Donald B. Hodges、George N. Karageorge、Daniel J. Keavy、Cathy D. Mahle、Ronald J. Mattson、Astrid A. Ortiz、Michael F. Parker、Katherine S. Takaki、Brett T. Watson、Joseph P.Yevich

  DOI：10.1016/j.bmc.2004.07.002

  日期：2004.9

  A series of fluoren-9-yl ethyl amides (2) were synthesized and evaluated for human melatonin MT1 and MT2 receptor binding. N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]propanamide (2b) was selected and evaluated in functional assays measuring intrinsic activity at the human MT1 and MT2 receptors and demonstrated full agonism at both receptors. The chronobiotic properties of 2b were demonstrated in both acute and chronic rat models where 2b produced an acute phase advance of 32 min at 1 mg/kg and chronically entrained free-running rats with a mean effective dose of 0.23 mg/kg. Compound 2b is significantly less efficacious than melatonin in constricting human coronary artery. (C) 2004 Elsevier Ltd. All rights reserved.