6-hydroxy-7-methoxy-4-oxochroman-2-carboxylic acid | 858859-51-5

• 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-methoxy-4-oxochroman-2-carboxylic acid
• 英文别名: 6-Hydroxy-7-methoxy-4-oxo-2,3-dihydrochromene-2-carboxylic acid
• CAS: 858859-51-5
• 化学式: C₁₁H₁₀O₆
• 分子量: 238.197
• InChiKey: ZXVFVKVHSMECEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-hydroxy-7-methoxy-4-oxochroman-2-carboxylic acid 在 palladium on activated charcoal 氢气 、 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 为溶剂， 生成 6-Hydroxy-7-methoxy-chroman-2-carboxylic acid propylamide
  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
• 作为产物：
  描述：

  2-甲氧基对苯二酚 在 三氯化铝 、 sodium acetate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 6-hydroxy-7-methoxy-4-oxochroman-2-carboxylic acid
  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

• Inhibitory effect of 6-hydroxy-7-methoxychroman-2-carboxylic acid phenylamide on nitric oxide and interleukin-6 production in macrophages
  作者：Kyung Rak Min、Heesoon Lee、Byung Hak Kim、EunYong Chung、Sung Min Cho、Youngsoo Kim

  DOI：10.1016/j.lfs.2005.05.046

  日期：2005.11

  6-Hydroxy-7-methoxychroman-2-carboxylic acid phenylamide (CP compound) is a novel chemically synthetic compound with vitamin E-like chemical structure. In the present study, the CP compound was discovered to inhibit nitric oxide (NO) and interleukin (IL)-6 productions in lipopolysaccharide (LPS)-stimulated macrophages. Further, CP compound attenuated LPS-induced synthesis of mRNA and protein levels of inducible NO synthase (iNOS), in parallel, and inhibited iNOS promoter activity. In the similar way, CP compound inhibited LPS-induced synthesis of IL-6 transcript but also IL-6 promoter activity. These results indicate that CP compound could down-regulate LPS-induced iNOS and IL-6 expression at the transcription step. As a mechanism of the anti-inflammatory action shown by CP compound, suppression of LPS-induced activation of both nuclear factor-kappa B (NF-kappa B) and activator protein-1 (AP-1) has been documented. Finally, CP compound could provide an invaluable tool to investigate LPS-induced NF-kappa B and AP-1 activation, in addition to its therapeutic potential in NO- and IL-6-associated inflammatory diseases. (c) 2005 Elsevier Inc. All rights reserved.
• 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.