Acetic acid 2-[4-(4-chloro-phenyl)-piperazine-1-carbonyl]-2,5,7,8-tetramethyl-chroman-6-yl ester | 210174-97-3

• 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: Acetic acid 2-[4-(4-chloro-phenyl)-piperazine-1-carbonyl]-2,5,7,8-tetramethyl-chroman-6-yl ester
• 英文别名: [2-[4-(4-Chlorophenyl)piperazine-1-carbonyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl] acetate
• CAS: 210174-97-3
• 化学式: C₂₆H₃₁ClN₂O₄
• 分子量: 470.996
• InChiKey: AZJJKFRWSNXNKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid 2-[4-(4-chloro-phenyl)-piperazine-1-carbonyl]-2,5,7,8-tetramethyl-chroman-6-yl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以93%的产率得到[4-(4-Chloro-phenyl)-piperazin-1-yl]-(6-hydroxy-2,5,7,8-tetramethyl-chroman-2-yl)-methanone
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of N-(aza)arylcarboxamides derived from Trolox®

  摘要：

  A series of 6-(aza) arylmethoxychroman-2-carboxamides 22-38, derived from Trolox(R) or 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, was prepared using two strategies, i.e. phenol blockade was carried out before or after amidification. These compounds were evaluated against peripheral inflammation by a carrageenin-induced foot-pad edema test. A permanent blockade of the phenol function by arylmethoxy groupings, in particular by the quinolylmethoxy moiety, was generally detrimental to activity; only the 6-benzyloxy and quinolylmethoxy derivatives 22 and 31 exhibited significant inhibition (58.3 and 97.1%) after oral administration of 0.4 mmol kg(-1). Among their 6-acetoxy or 6-hydroxy precursors 12-21, evaluated at 0.4 and 0.1 mmol kg(-1), the N-(4-pyridyl) chromancarboxamides 15 and 20 exerted the highest inhibitory activity. Their ID50 were 14.7 +/- 5.5 mg kg(-1) and 14.7 +/- 4.5 mg kg(-1), respectively. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80065-2
• 作为产物：
  描述：

  1-(4-氯苯基)哌嗪 、 6-acetoxy-2,5,7,8-tetramethylchromane-2-carboxylic acid 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以70%的产率得到Acetic acid 2-[4-(4-chloro-phenyl)-piperazine-1-carbonyl]-2,5,7,8-tetramethyl-chroman-6-yl ester
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of N-(aza)arylcarboxamides derived from Trolox®

  摘要：

  A series of 6-(aza) arylmethoxychroman-2-carboxamides 22-38, derived from Trolox(R) or 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid, was prepared using two strategies, i.e. phenol blockade was carried out before or after amidification. These compounds were evaluated against peripheral inflammation by a carrageenin-induced foot-pad edema test. A permanent blockade of the phenol function by arylmethoxy groupings, in particular by the quinolylmethoxy moiety, was generally detrimental to activity; only the 6-benzyloxy and quinolylmethoxy derivatives 22 and 31 exhibited significant inhibition (58.3 and 97.1%) after oral administration of 0.4 mmol kg(-1). Among their 6-acetoxy or 6-hydroxy precursors 12-21, evaluated at 0.4 and 0.1 mmol kg(-1), the N-(4-pyridyl) chromancarboxamides 15 and 20 exerted the highest inhibitory activity. Their ID50 were 14.7 +/- 5.5 mg kg(-1) and 14.7 +/- 4.5 mg kg(-1), respectively. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80065-2