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6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid pyridin-3-ylamide | 144000-15-7

中文名称
——
中文别名
——
英文名称
6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid pyridin-3-ylamide
英文别名
6-hydroxy-2,5,7,8-tetramethyl-N-pyridin-3-yl-3,4-dihydrochromene-2-carboxamide
6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid pyridin-3-ylamide化学式
CAS
144000-15-7
化学式
C19H22N2O3
mdl
——
分子量
326.395
InChiKey
UEEMQNFTCCQHHF-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.1
  • 重原子数:
    24
  • 可旋转键数:
    2
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.37
  • 拓扑面积:
    71.4
  • 氢给体数:
    2
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    2-(氯甲基)喹啉6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid pyridin-3-ylamidecaesium carbonate 作用下, 以 乙腈 为溶剂, 反应 12.0h, 以75%的产率得到2,5,7,8-Tetramethyl-6-(quinolin-2-ylmethoxy)-chroman-2-carboxylic acid pyridin-3-ylamide
    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:
    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
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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.
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