3,4-diamino-naphthalene-1-sulfonic acid amide | 118876-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,4-diamino-naphthalene-1-sulfonic acid amide
• 英文别名: 3,4-diamino-naphthalene-1-sulphonamide；1,2-diamino-4-sulphamoyl-naphtalene；1-Naphthalenesulfonamide, 3,4-diamino-；3,4-diaminonaphthalene-1-sulfonamide
• CAS: 118876-83-8
• 化学式: C₁₀H₁₁N₃O₂S
• 分子量: 237.282
• InChiKey: MMIXHYFPKVUVIB-UHFFFAOYSA-N

物化性质

• 沸点：
  555.8±60.0 °C(Predicted)
• 密度：
  1.510±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  oxalic acid dihydrate 、 3,4-diamino-naphthalene-1-sulfonic acid amide 以 盐酸 为溶剂， 以0.6 g (50%)的产率得到2,3-Dihydroxy-6-sulphamoyl-benzo(f)quinoxaline
  参考文献：
  名称：

  Heterocyclic compounds and their preparation and use

  摘要：

  具有以下式子的杂环二羟基喹喔啉化合物##STR1##其中--A--与标记为1和2的两个碳原子一起从##STR2##中选择，R.sup.1，R.sup.2和R.sup.3独立地为H，卤素，CN，NH.sub.2，NO.sub.2，SO.sub.3 H，SO.sub.2 NH.sub.2或CONH.sub.2。本发明还涉及制备该化合物的方法，其药物组成物以及其用途。这些化合物在治疗兴奋性神经递质过度活跃引起的症状方面是有用的。

  公开号：

  US04889855A1
• 作为产物：
  描述：

  congo red 在 palladium on activated charcoal ammonium hydroxide 、 五氯化磷 、 一水合肼 、 三氯氧磷 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 23.5h， 生成 3,4-diamino-naphthalene-1-sulfonic acid amide
  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

文献信息

• Pyridoquinoxaline compounds and their preparation and use as glutamate
  申请人：A/S Ferrosan

  公开号：US04912108A1

  公开（公告）日：1990-03-27

  Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein --A-- together with the two carbon atoms denoted as 1 and 2 is selected from ##STR2## R.sup.1, R.sup.2 and R.sup.3 are independently H, halogen, CN, NH.sub.2, NO.sub.2, SO.sub.3 H, SO.sub.2 NH.sub.2, or CONH.sub.2 The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use. The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters.

  具有以下式子的杂环二羟基喹喔啉化合物 ##STR1## 其中--A--与标记为1和2的两个碳原子一起从以下选择 ##STR2## R.sup.1，R.sup.2和R.sup.3独立地为H，卤素，CN，NH.sub.2，NO.sub.2，SO.sub.3 H，SO.sub.2 NH.sub.2或CONH.sub.2。本发明还涉及制备该化合物的方法，其制药组合物以及它们的用途。该化合物在治疗由兴奋性神经递质的过度活跃引起的症状方面是有用的。
• US4889855A
  申请人：——

  公开号：US4889855A

  公开（公告）日：1989-12-26
• US4912108A
  申请人：——

  公开号：US4912108A

  公开（公告）日：1990-03-27
• Congo red analogues as potential anti-prion agents
  作者：Stefania Villa、Giorgio Cignarella、Daniela Barlocco、Marco Gervasoni、Gabriella Carcassola、Laura Giannino、Paolo Mantegazza

  DOI：10.1016/s0014-827x(03)00151-4

  日期：2003.9

  '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).
• Heterocyclic compounds and their preparation and use
  申请人：A/S Ferrosan

  公开号：US04889855A1

  公开（公告）日：1989-12-26

  Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein --A-- together with the two carbon atoms denoted as 1 and 2 is selected from ##STR2## R.sup.1, R.sup.2 and R.sup.3 are independently H, halogen, CN, NH.sub.2, NO.sub.2, SO.sub.3 H, SO.sub.2 NH.sub.2, or CONH.sub.2 The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use. The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters.

  具有以下式子的杂环二羟基喹喔啉化合物##STR1##其中--A--与标记为1和2的两个碳原子一起从##STR2##中选择，R.sup.1，R.sup.2和R.sup.3独立地为H，卤素，CN，NH.sub.2，NO.sub.2，SO.sub.3 H，SO.sub.2 NH.sub.2或CONH.sub.2。本发明还涉及制备该化合物的方法，其药物组成物以及其用途。这些化合物在治疗兴奋性神经递质过度活跃引起的症状方面是有用的。