1,2,2-trimethyl-4-(4-nitrophenyl)piperazine | 915723-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1,2,2-trimethyl-4-(4-nitrophenyl)piperazine
• CAS: 915723-09-0
• 化学式: C₁₃H₁₉N₃O₂
• 分子量: 249.313
• InChiKey: KHJBPXHXSDVQNW-UHFFFAOYSA-N

物化性质

• 沸点：
  373.3±37.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,2-trimethyl-4-(4-nitrophenyl)piperazine 在 palladium on activated charcoal 对甲苯磺酸 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 6-fluoro-4-[4-(3,3,4-trimethylpiperazin-1-yl)phenylamino]quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Structure−Activity Relationship of Quinoline Derivatives as Potent and Selective α_2C-Adrenoceptor Antagonists

  摘要：

  Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human alpha(2)-adrenoceptor subtypes (alpha(2A), alpha(2B), and alpha(2C.)). A number of compounds with good antagonist potencies against the alpha(2C)-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl) phenylamino] quinolin- 3- yl} methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the alpha(2C)-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the alpha(2C)-adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

  DOI：

  10.1021/jm060262x
• 作为产物：
  描述：

  5,5-dimethyl-1-(4-nitrophenyl)piperazin-2-one 在 硼烷四氢呋喃络合物 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1,2,2-trimethyl-4-(4-nitrophenyl)piperazine
  参考文献：
  名称：

  Structure−Activity Relationship of Quinoline Derivatives as Potent and Selective α_2C-Adrenoceptor Antagonists

  摘要：

  Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human alpha(2)-adrenoceptor subtypes (alpha(2A), alpha(2B), and alpha(2C.)). A number of compounds with good antagonist potencies against the alpha(2C)-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl) phenylamino] quinolin- 3- yl} methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the alpha(2C)-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the alpha(2C)-adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

  DOI：

  10.1021/jm060262x

文献信息

• [EN] PYRIMIDOPYRIMIDINONES USEFUL AS WEE-1 KINASE INHIBITORS<br/>[FR] PYRIMIDOPYRIMIDINONES UTILES COMME INHIBITEURS DE LA WEE-1 KINASE
  申请人：ALMAC DISCOVERY LTD

  公开号：WO2015092431A1

  公开（公告）日：2015-06-25

  The present invention relates to compounds that are useful as inhibitors of the activity of Wee-1 kinase. The present invention also relates to pharmaceutical compositions comprising these compounds and to methods of using these compounds in the treatment of cancer and methods of treating cancer.

  本发明涉及一类可用作Wee-1激酶活性抑制剂的化合物。本发明还涉及包含这些化合物的药物组合物以及使用这些化合物治疗癌症的方法和治疗癌症的方法。
• TRIAZOLOPYRIDINE COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE & INFLAMMATORY DISEASES
  申请人：Galapagos N.V.

  公开号：EP2086540A1

  公开（公告）日：2009-08-12
• PYRIMIDOPYRIMIDINONES USEFUL AS WEE-1 KINASE INHIBITORS
  申请人：Almac Discovery Limited

  公开号：EP3083625A1

  公开（公告）日：2016-10-26
• US9850247B2
  申请人：——

  公开号：US9850247B2

  公开（公告）日：2017-12-26
• [EN] TRIAZOLOPYRIDINE COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE & INFLAMMATORY DISEASES<br/>[FR] COMPOSÉS DE TRIAZOLOPYRIDINE POUR LE TRAITEMENT DE MALADIES DÉGÉNÉRATIVES ET INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2008065198A1

  公开（公告）日：2008-06-05

  [EN] Novel triazolopyridine compounds are disclosed that have a formula represented by Formula (I). The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non- limiting example, ECM degradation, joint degradation and/or inflammation, and others.
  [FR] L'invention concerne de nouveaux composés de triazolopyridine représentéw par la formule suivante : (I). Ces composés peuvent être préparés sous forme de compositions pharmaceutiques, et être utilisés pour la prévention et le traitement de divers troubles chez les mammifères, y compris l'homme, notamment, à titre d'exemples sans valeur limitative, la dégradation de la matrice extracellulaire, la dégradation des articulations et/ou les inflammations, etc.