6-hydroxy-5-[3-(4-phenyl-1-piperazinyl)propoxy]indane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-hydroxy-5-[3-(4-phenyl-1-piperazinyl)propoxy]indane
• 英文别名: 6-[3-(4-phenylpiperazin-1-yl)propoxy]-2,3-dihydro-1H-inden-5-ol
• 化学式: C₂₂H₂₈N₂O₂
• 分子量: 352.477
• InChiKey: HTIIEWJMAIWDTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,6-二甲氧基茚酮 在 钯 盐酸 、 氢氧化钾 、 氢气 、 sodium ethanolate 、 三溴化硼 、 三乙胺 、 汞 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 21.0h， 生成 6-hydroxy-5-[3-(4-phenyl-1-piperazinyl)propoxy]indane
  参考文献：
  名称：

  Synthesis and antianxiety activity of (.omega.-piperazinylalkoxy)indan derivatives

  摘要：

  A series of (omega-piperazinylalkoxy)indan derivatives has been synthesized and screened for potential antianxiety activities. The effect of structural modification of these molecules on activities has been systemically examined. Antianxiety activity was displayed by 5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (2), 5-[3-[4-(4-fluorophenyl)-1-piperazinyl]-propoxy]indan (8), 6-fluoro-5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (33), and 6-methyl-5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (42), as determined in antifighting and anti-morphine tests. These derivatives in antianxiety tests were equipotent or more potent than chlordiazepoxide with less muscle-relaxant effect. They also showed weak neuroleptic-like action.

  DOI：

  10.1021/jm00356a024

文献信息

• Piperazinylalkoxyindanes and acid addition salts thereof
  申请人：MITSUBISHI KASEI CORPORATION

  公开号：EP0021368A1

  公开（公告）日：1981-01-07

  Piperazinylalkoxyindanes having the general formula wherein n is an integer of 3 or 4; R1 is hydrogen, halogen, alkyl, alkoxy, hydroxy, phenyl or nitro; and R2 is phenyl or pyridyl optionally having at least one substituent selected from the group consisting of halogen, trifluoromethyl, alkoxy and alkylcarbonyl, and acid addition salts thereof are disclosed, which have anti-anxiety activity and are effective as sedatives.

  通式如下的哌嗪基烷氧基茚满酮 其中 n 是 3 或 4 的整数；R1 是氢、卤素、烷基、烷氧基、羟基、苯基或硝基；R2 是苯基或吡啶基，可选择具有至少一个从卤素、三氟甲基、烷氧基和烷基羰基组成的组中选出的取代基，本发明公开了这些化合物及其酸加成盐，它们具有抗焦虑活性，可有效用作镇静剂。
• US4339580A
  申请人：——

  公开号：US4339580A

  公开（公告）日：1982-07-13
• Synthesis and antianxiety activity of (.omega.-piperazinylalkoxy)indan derivatives
  作者：Ryoji Kikumoto、Akihiro Tobe、Harukazu Fukami、Mitsuo Egawa

  DOI：10.1021/jm00356a024

  日期：1983.2

  A series of (omega-piperazinylalkoxy)indan derivatives has been synthesized and screened for potential antianxiety activities. The effect of structural modification of these molecules on activities has been systemically examined. Antianxiety activity was displayed by 5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (2), 5-[3-[4-(4-fluorophenyl)-1-piperazinyl]-propoxy]indan (8), 6-fluoro-5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (33), and 6-methyl-5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (42), as determined in antifighting and anti-morphine tests. These derivatives in antianxiety tests were equipotent or more potent than chlordiazepoxide with less muscle-relaxant effect. They also showed weak neuroleptic-like action.