N-(2,6-Dimethylphenyl)-(6-acetoxy-3,4-dihydro-2,5,7,8-tetramethyl-2H[1]-benzopyran-2-yl)carboxamide | 146427-85-2

• 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-acetoxy-3,4-dihydro-2,5,7,8-tetramethyl-2H[1]-benzopyran-2-yl)carboxamide
• 英文别名: N-(2,6-dimethylphenyl)-6-acetoxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxamide；[2-[(2,6-Dimethylphenyl)carbamoyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl] acetate
• CAS: 146427-85-2
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: QLGQKMIMZVOMTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,6-Dimethylphenyl)-(6-acetoxy-3,4-dihydro-2,5,7,8-tetramethyl-2H[1]-benzopyran-2-yl)carboxamide 在 sodium hydroxide 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6-(4-Fluoro-benzyloxy)-2,5,7,8-tetramethyl-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：

  2,6-二甲基苯胺 、 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62%的产率得到N-(2,6-Dimethylphenyl)-(6-acetoxy-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

• Benzopyran compounds
  申请人：Adir et Compagnie

  公开号：US05393775A1

  公开（公告）日：1995-02-28

  A compound selected from those of formula (I): ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and n are as defined in the description, its optical isomers, and its addition salts thereof with a pharmaceutically-acceptable acid or base, and medicinal product containing the same for treating a mammal afflicted with a disorder connected with peroxydation processes and biosynthesis of eicosanoids.

  从以下化学式（I）中选择的化合物：##STR1## 其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5，R.sub.6，R.sub.7，R.sub.8，R.sub.9和n如描述中所定义，其光学异构体及其与药学上可接受的酸或碱形成的加合物盐，以及含有该化合物的药物产品，用于治疗患有与过氧化作用过程和前列腺素生物合成相关的疾病的哺乳动物。
• 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
• US5393775A
  申请人：——

  公开号：US5393775A

  公开（公告）日：1995-02-28
• US5395834A
  申请人：——

  公开号：US5395834A

  公开（公告）日：1995-03-07