3-phenethylaminoindan-1-one | 861856-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3-phenethylaminoindan-1-one
• 英文别名: 3-benzylmethylamino-1-indanone；3-Benzylmethylaminoindan-1-one；3-(2-phenylethylamino)-2,3-dihydroinden-1-one
• CAS: 861856-86-2
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: KPOLJCXGLWOGDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenethylaminoindan-1-one 、 溴甲烷 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 生成 3-benzylmethylamino-1-methylindan-1-ol
  参考文献：
  名称：

  Substituted 7,12-methano dibenzazocines

  摘要：

  7,12-甲烷二苯并咪唑啉类化合物，例如7,13-二氢-6,12-二甲基-7,12-甲烷-6H-二苯并[c,f]咪唑啉，通过环化3-苄氨基烷基茚-1-醇制备，可用作抗炎药物。

  公开号：

  US03985729A1
• 作为产物：
  描述：

  1-茚酮 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 3-phenethylaminoindan-1-one
  参考文献：
  名称：

  A new amino-masking group capable of pH-triggered amino-drug release

  摘要：

  The prodrug approach is potentially useful for mitigating pharmaceutical problems-such as poor membrane permeability or stability-which commonly occur with amino drugs. On the other hand there persists a dearth of useful systems for masking amines that satisfy the prodrug requirements of good in vitro stability coupled with predictable and rapid drug release in response to a local tissue condition. This study describes an evaluation of aminoindanes as bioreversibly masked amines poised to undergo elimination to the parent amine. Several model amine and amino drug indanone derivatives were synthesised. pK(a) values were determined by capillary electrophoresis and pH rate profiles for elimination and amine liberation were measured. The aminoindanone system appears to have particular applicability to secondary amino substrates whose indanone derivatives are stable at low pH but undergo drug release at rates corresponding to first-order half-lives of < 5 min at pH 7.4. (c) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2004.11.006

文献信息

• US3985729A
  申请人：——

  公开号：US3985729A

  公开（公告）日：1976-10-12
• Substituted 7,12-methano dibenzazocines
  申请人：Sandoz, Inc.

  公开号：US03985729A1

  公开（公告）日：1976-10-12

  Substituted 7,12-methano-dibenzazocines, e.g., 7,13-dihydro-6,12-dimethyl-7,12-methano-6H-dibenz[c,f]azocine, are prepared by cyclizing 3-benzylamino-alkyl-indan-1-ols and are useful as anti-inflammatory agents.

  7,12-甲烷二苯并咪唑啉类化合物，例如7,13-二氢-6,12-二甲基-7,12-甲烷-6H-二苯并[c,f]咪唑啉，通过环化3-苄氨基烷基茚-1-醇制备，可用作抗炎药物。
• A new amino-masking group capable of pH-triggered amino-drug release
  作者：John F. Gilmer、Ana Luísa Simplício、John M. Clancy

  DOI：10.1016/j.ejps.2004.11.006

  日期：2005.3

  The prodrug approach is potentially useful for mitigating pharmaceutical problems-such as poor membrane permeability or stability-which commonly occur with amino drugs. On the other hand there persists a dearth of useful systems for masking amines that satisfy the prodrug requirements of good in vitro stability coupled with predictable and rapid drug release in response to a local tissue condition. This study describes an evaluation of aminoindanes as bioreversibly masked amines poised to undergo elimination to the parent amine. Several model amine and amino drug indanone derivatives were synthesised. pK(a) values were determined by capillary electrophoresis and pH rate profiles for elimination and amine liberation were measured. The aminoindanone system appears to have particular applicability to secondary amino substrates whose indanone derivatives are stable at low pH but undergo drug release at rates corresponding to first-order half-lives of < 5 min at pH 7.4. (c) 2004 Elsevier B.V. All rights reserved.