6-hydroxy-7-methoxychroman-2-carboxylic acid (3-nitrophenyl)amide

• 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: 6-hydroxy-7-methoxychroman-2-carboxylic acid (3-nitrophenyl)amide
• 英文别名: CP-1158；6-hydroxy-7-methoxy-N-(3-nitrophenyl)-3,4-dihydro-2H-chromene-2-carboxamide
• 化学式: C₁₇H₁₆N₂O₆
• 分子量: 344.324
• InChiKey: CVBWXWOPJFUAEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-甲氧基对苯二酚 在 palladium on activated charcoal 三氯化铝 、 氢气 、 sodium acetate 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 6-hydroxy-7-methoxychroman-2-carboxylic acid (3-nitrophenyl)amide
  参考文献：
  名称：

  Synthesis and evaluation of 6-hydroxy-7-methoxy-4-chromanone- and chroman-2-carboxamides as antioxidants

  摘要：

  A series of 6-hydroxy-7-methoxy-4-chromanone- (2a-e) and chroman-2-carboxamides (3a-e) were synthesized and their antioxidant activities were evaluated. While compounds 2a-e were less active, compounds 3a-e exhibited more potent inhibition of lipid peroxidation initiated by Fe2+ and ascorbic acid in rat brain homogenates. Among them, N-arylsubstituted-chroman-2-carboxamides (3d and 3e) exhibited 25-40 times more potent inhibition than trolox (1). The DPPH radical scavenging activity of compound 3d was comparable to that of trolox. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.118

文献信息

• Synthesis and evaluation of 6-hydroxy-7-methoxy-4-chromanone- and chroman-2-carboxamides as antioxidants
  作者：Heesoon Lee、Keumho Lee、Jae-Kyung Jung、Jungsook Cho、Emmanuel A. Theodorakis

  DOI：10.1016/j.bmcl.2005.03.118

  日期：2005.6

  A series of 6-hydroxy-7-methoxy-4-chromanone- (2a-e) and chroman-2-carboxamides (3a-e) were synthesized and their antioxidant activities were evaluated. While compounds 2a-e were less active, compounds 3a-e exhibited more potent inhibition of lipid peroxidation initiated by Fe2+ and ascorbic acid in rat brain homogenates. Among them, N-arylsubstituted-chroman-2-carboxamides (3d and 3e) exhibited 25-40 times more potent inhibition than trolox (1). The DPPH radical scavenging activity of compound 3d was comparable to that of trolox. (c) 2005 Elsevier Ltd. All rights reserved.