6-[(7-Chloroquinolin-2-yl)methoxy]-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid | 208039-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-[(7-Chloroquinolin-2-yl)methoxy]-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid
• CAS: 208039-86-5
• 化学式: C₂₄H₂₄ClNO₄
• 分子量: 425.912
• InChiKey: BTGFPAMHNOKVCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基-4,6-二甲基吡啶 、 6-[(7-Chloroquinolin-2-yl)methoxy]-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以72%的产率得到6-[(7-chloroquinolin-2-yl)methoxy]-N-(4,6-dimethylpyridin-2-yl)-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide
  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：

  奎诺二甲基丙烯酸酯 在 sodium hydroxide 、 氯化亚砜 、 potassium carbonate 、 caesium carbonate 、 sodium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 32.0h， 生成 6-[(7-Chloroquinolin-2-yl)methoxy]-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid
  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

文献信息

• Synthesis and anti-inflammatory activity of N-(aza)arylcarboxamides derived from Trolox®
  作者：Claudie Moulin、Muriel Duflos、Guillaume Le Baut、Nicole Grimaud、Pierre Renard、Daniel-Henri Caignard

  DOI：10.1016/s0223-5234(98)80065-2

  日期：1998.4

  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.