3-nitro-4-amino-naphthalene-1-carboxylic acid | 675877-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-nitro-4-amino-naphthalene-1-carboxylic acid
• 英文别名: 4-Amino-3-nitro-1-naphthalenecarboxylic acid；4-amino-3-nitronaphthalene-1-carboxylic acid
• CAS: 675877-58-4
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: IAJOHKOCPWTEHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106.46
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-nitro-4-amino-naphthalene-1-carboxylic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 3,4-diamino-naphthalene-1-carboxylic acid
  参考文献：
  名称：

  Congo red analogues as potential anti-prion agents

  摘要：

  'Transmissible Spongiform Encephalopathies' (TSE) are a group of degenerative, progressive and fatal disorders of CNS which affect both humans and animals, characterised by a long incubation time. The pathogenetic mechanism in TSE is the conversion of normal prion protein (PrP(sen)) to an altered protease resistant isoform (PrP(res)) that accumulates in amyloid deposits into the brain; therefore, PrP(res) is the primary target for therapeutic strategies. The discovery that the sulphonated azo dye Congo red (CR) is able to inhibit the replications of TSE agents and the accumulation of PrP(res) in animals and in scrapie infected mouse neuroblastoma cells induced us to designe molecules structurally related to CR (1a-f, 2f,g). The compounds were tested in vitro to evaluate their interaction with 263K PrP(res). Six of the tested compounds were found to interact with PrP(res) molecules and to over-stabilise the PrP(res) aggregates, as CR does. However, none of them induced the reversion of PrP(res) to PrP(sen).

  DOI：

  10.1016/s0014-827x(03)00151-4
• 作为产物：
  描述：

  3-硝基-1-萘甲酸 在 氢氧化钾 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以44.5%的产率得到3-nitro-4-amino-naphthalene-1-carboxylic acid
  参考文献：
  名称：

  Congo red analogues as potential anti-prion agents

  摘要：

  'Transmissible Spongiform Encephalopathies' (TSE) are a group of degenerative, progressive and fatal disorders of CNS which affect both humans and animals, characterised by a long incubation time. The pathogenetic mechanism in TSE is the conversion of normal prion protein (PrP(sen)) to an altered protease resistant isoform (PrP(res)) that accumulates in amyloid deposits into the brain; therefore, PrP(res) is the primary target for therapeutic strategies. The discovery that the sulphonated azo dye Congo red (CR) is able to inhibit the replications of TSE agents and the accumulation of PrP(res) in animals and in scrapie infected mouse neuroblastoma cells induced us to designe molecules structurally related to CR (1a-f, 2f,g). The compounds were tested in vitro to evaluate their interaction with 263K PrP(res). Six of the tested compounds were found to interact with PrP(res) molecules and to over-stabilise the PrP(res) aggregates, as CR does. However, none of them induced the reversion of PrP(res) to PrP(sen).

  DOI：

  10.1016/s0014-827x(03)00151-4