3-氨基-6-(苯硫基)哒嗪 | 90844-35-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 哒嗪类化合物
• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 3-氨基-6-(苯硫基)哒嗪
• 中文别名: 3-氨基-6-苯基硫哒嗪
• 英文名称: 3-amino-6-phenylthiopyridazine
• 英文别名: 6-phenylsulfanyl-pyridazin-3-ylamine；6-Phenylmercapto-pyridazin-3-ylamin；3-Amino-6-(phenylthio)pyridazine；6-phenylsulfanylpyridazin-3-amine
• CAS: 90844-35-2
• 化学式: C₁₀H₉N₃S
• 分子量: 203.268
• InChiKey: ZVESEBXJNCNXPH-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C
• 沸点：
  476.3±30.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-氨基-6-(苯硫基)哒嗪 在 磷酸 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 2-benzyl-3-dimethylaminomethyl-6-phenylthioimidazo<1,2-b>pyridazine
  参考文献：
  名称：

  Barlin, Gordon B.; Davies, Les P.; Ireland, Stephen J., Australian Journal of Chemistry, 1992, vol. 45, # 8, p. 1281 - 1300

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(6-氯-3-哒嗪基)乙酰胺 在 1,3-二甲基-2-咪唑啉酮 、 potassium tert-butylate 、 苯硫酚 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以60%的产率得到3-氨基-6-(苯硫基)哒嗪
  参考文献：
  名称：

  酰胺阴离子作为亲核杂芳族取代中的意外活化基团

  摘要：

  与中性酰胺基和氨基取代基相比，乙酰氨基阴离子取代基意外地在哒嗪，酞嗪，噻唑和噻二唑中用醇盐进行卤化物的亲核置换。

  DOI：

  10.1016/0040-4039(96)00734-4

文献信息

• A revision of the alcoholysis and alkanethiolysis of 3-amino-6-chloropyridazine
  作者：Bert U. W. Maes、Guy L. F. Lemière、Roger Dommisse、Achiel Haemers

  DOI：10.1002/jhet.5570380530

  日期：2001.9

  The synthesis of 3-amino-6-alkoxy- and 3-amino-6-alkylthiopyridazines via nucleophilic aromatic substitution on 3-amino-6-chloropyridazine is described. In contrast to literature reports, no pressure tube is required to perform these reactions.

  描述了通过在3-氨基-6-氯哒嗪上的亲核芳族取代合成3-氨基-6-烷氧基-和3-氨基-6-烷基硫代哒嗪。与文献报道相反，不需要压力管来进行这些反应。
• Imidazo[1,2-B]pyridazines. II. 6-Alkylthio and 6-Arylthio-3-methoxy-2-phenylimidazo[1,2-b]pyridazines
  作者：GB Barlin、SJ Ireland

  DOI：10.1071/ch9871491

  日期：——

  A series of 6-alkylthio- and 6-arylthio-3-methoxy-2-phenylimidazo[l,2- b]pyridazines has been prepared from 6-alkylthio-and 6-arylthio-pyridazin-3-amines through the corresponding 6-alkylthio-and 6-arylthio-2-phenylimidazo[l,2-b] pyridazin-3(5H)-ones.

  通过相应的 6-烷硫基和 6-芳硫基-2-苯基咪唑并[l,2-b]哒嗪-3(5H)-酮，从 6-烷硫基和 6-芳硫基哒嗪-3-胺制备了一系列 6-烷硫基和 6-芳硫基-3-甲氧基-2-苯基咪唑并[l,2-b]哒嗪。
• Imidazo[1,2-b]Pyridazines. XIX. Syntheses and Central Nervous System Activities of Some 6-Arylthio(aryloxy and alkylthio)-3-(acetamidomethyl, benzamidomethyl, methoxy and unsubstituted)-2-arylimidazo[1,2-b]pyridazines
  作者：GB Barlin、LP Davies、SJ Ireland

  DOI：10.1071/ch9960443

  日期：——

  Some 6-arylthio( aryloxy and alkylthio )-3-( acetamidomethyl , benzamidomethyl, methoxy and unsubstituted )-2-arylimidazo[1,2-b] pyridazines have been prepared and examined for their ability to displace [3H]diazepam from rat brain membranes. The most active compound was 3-acetamidomethyl-2-(3',4'-methylenedioxyphenyl)-6-phenylthioimidazo[1,2-b] pyridazine with IC50 4.4 nM. The 3-acylaminomethyl-6-(2- and 3-methoxyphenylthio)-2-phenylimidazo[1,2-b] pyridazines proved less active than their 6-phenylthio analogues, and larger substituents at the 2- and 6-positions markedly decreased binding. Significant differences in binding ability have been observed between 3-acylaminomethyl-2-aryl-6-phenylthioimidazo[1,2-b] pyridazines and the corresponding imidazo [1,2-a]pyridines.

  已准备并检查了一些6-芳基硫（芳氧基和烷基硫）-3-（乙酰胺甲基，苯甲酰胺甲基，甲氧基和未取代）-2-芳基咪唑并[1,2-b]吡啶并[1,2-b]吡啶，以评估它们从大鼠脑膜中置换[3H]地西泮的能力。最活跃的化合物是3-乙酰胺甲基-2-(3',4'-亚甲氧基苯基)-6-苯基硫代咪唑并[1,2-b]吡啶，IC50为4.4纳摩尔。3-酰胺基甲基-6-(2-和3-甲氧基苯硫基)-2-苯基咪唑并[1,2-b]吡啶比它们的6-苯基硫类似物活性较低，2-和6-位置的较大取代基显著降低了结合能力。在3-酰胺基甲基-2-芳基-6-苯基硫代咪唑并[1,2-b]吡啶和相应的咪唑并[1,2-a]吡啶之间观察到了显著的结合能力差异。
• Imidazo[1,2-b]Pyridazines. XXI. Syntheses of Some 3-Acylaminomethyl-6-(chloro, fluoro, methoxy, methylthio, phenoxy and phenylthio)-2-(phenyl, 4-t-butylphenyl, 4-cyclohexylphenyl, β-naphthyl and styryl)imidazo[1,2-b]pyridazines and Their Interaction With Central and Peripheral-Type Benzodiazepine Receptors
  作者：GB Barlin、LP Davies、PW Harrison、SJ Ireland、AC Willis

  DOI：10.1071/ch9960451

  日期：——

  Some 3-(aliphatic and aromatic) acylaminomethyl derivatives of 6-( chloro, fluoro, methoxy, methylthio, phenoxy and phenylthio )-2-(phenyl, 4-t-butylphenyl, 4-cyclohexylphenyl, β- naphthyl and styryl ) imidazo [1,2-b] pyridazines have been prepared and tested for binding to central benzodiazepine receptors present in rat brain membrane, and to peripheral-type (mitochondrial) benzodiazepine receptors present in rat kidney membrane. Some of these compounds which contained 2-(4-t-butylphenyl, 4-cyclohexylphenyl and styryl ) substituents bound strongly and selectively to peripheral-type benzodiazepine receptors. For example, 2-(4′-t-butylphenyl)-6-chloro-2-(4″-fluorobenzamidomethyl) imidazo [1,2-b] pyridazine in tests for the displacement of [3H]diazepam from both peripheral-type and central benzodiazepine receptors gave IC50 <1.0 nM and 9% displacement at 1000 nM , respectively. Steric effects appeared to be more restrictive in the interaction of these ligands with central benzodiazepine receptors rather than with peripheral-type benzodiazepine receptors; X-ray structure analyses of two typical compounds are reported.

  一些6-(氯、氟、甲氧基、甲硫氧基、苯氧基和苯硫氧基)基-2-(苯基、4-叔丁基苯基、4-环己基苯基、β-萘基和芳基)咪唑[1,2-b]吡啶嗪的3-(脂肪和芳香族)酰胺甲基衍生物已制备并测试其与大鼠脑膜中存在的中枢苯二氮卓类受体以及大鼠肾膜中存在的外周型（线粒体）苯二氮卓类受体的结合。其中一些含有2-(4-叔丁基苯基、4-环己基苯基和芳基)取代基的化合物与外周型苯二氮卓类受体结合强烈且具有选择性。例如，在对2-(4'-叔丁基苯基)-6-氯-2-(4''-氟苯甲酰胺基甲基)咪唑[1,2-b]吡啶嗪进行[3H]地西泮从外周型和中枢苯二氮卓类受体的位点上的置换测试时，其IC50 <1.0 nM，分别在1000 nM时分别表现为9%的置换。立体效应似乎在这些配体与中枢苯二氮卓类受体的相互作用中更具限制性，而不是与外周型苯二氮卓类受体的相互作用；报道了两种典型化合物的X射线结构分析结果。
• Synthesis of imidazo[1,2-<i>b</i>]pyridazines: Fenbendazole, oxifenbendazole analogs and related derivatives
  作者：Alaa E. Mourad、Dean S. Wise、Leroy B. Townsend

  DOI：10.1002/jhet.5570300531

  日期：1993.10

  A series of imidazo[1,2-b]pyridazines has been prepared and evaluated for macrofilaricidal activity against Brugia pahangi or Acanthocheilonema viteae infections in jirds. The imidazo[1,2-b]pyridazine analogs of fen-bendazole and oxifenbendazole are reported. In addition, several 6-aminoimidazo[1,2-b]pyridazine derivatives have been prepared. None of these compounds possessed significant activity against

  已经制备了一系列咪唑并[1,2- b ]哒嗪，并评估了其对吉氏布鲁格氏菌或棘阿米德酵母菌感染的大杀线虫活性。报道了芬苯达唑和奥芬苯达唑的咪唑并[1,2- b ]哒嗪类似物。另外，已经制备了几种6-氨基咪唑并[1,2- b ]哒嗪衍生物。这些化合物均不具有针对人巨细胞病毒（HCMV）或丝虫感染的显着活性。