N-(2,6-Dimethylphenyl)-(6-hydroxy-3,4-dihydro-2,5,7,8-tetramethyl-2H[1]-benzopyran-2-yl)carboxamide | 146427-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(2,6-Dimethylphenyl)-(6-hydroxy-3,4-dihydro-2,5,7,8-tetramethyl-2H[1]-benzopyran-2-yl)carboxamide
• 英文别名: N-(2,6-dimethylphenyl)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide
• CAS: 146427-79-4
• 化学式: C₂₂H₂₇NO₃
• 分子量: 353.461
• InChiKey: PYHDVDDSGWOQQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(氯甲基)喹啉 、 N-(2,6-Dimethylphenyl)-(6-hydroxy-3,4-dihydro-2,5,7,8-tetramethyl-2H[1]-benzopyran-2-yl)carboxamide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以55%的产率得到2,5,7,8-Tetramethyl-6-(quinolin-2-ylmethoxy)-chroman-2-carboxylic acid (2,6-dimethyl-phenyl)-amide
  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：

  6-acetoxy-2,5,7,8-tetramethylchromane-2-carboxylic acid 在 sodium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 17.0h， 生成 N-(2,6-Dimethylphenyl)-(6-hydroxy-3,4-dihydro-2,5,7,8-tetramethyl-2H[1]-benzopyran-2-yl)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

文献信息

• Nouveaux composés benzopyraniques, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP0512899A1

  公开（公告）日：1992-11-11

  Composés de formule I : dans laquelle R₁, R₂, R₃, R₄, R₅, R₆, R₇, X, et n sont définis dans la description,    leurs isomères optiques, et leurs sels d'addition à une base ou à un acide pharmaceutiquement acceptable. Médicaments.

  式 I 的化合物： 其中 R₁、R₂、R₃、R₄、R₅、R₆、R₇、X 和 n 如说明中所定义、 它们的光学异构体、 及其与药学上可接受的碱或酸的加成盐。 药物。
• US5315017A
  申请人：——

  公开号：US5315017A

  公开（公告）日：1994-05-24
• 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.