5-dimethylamino-2-nitrobenzonitrile | 96336-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-dimethylamino-2-nitrobenzonitrile
• 英文别名: 5-(Dimethylamino)-2-nitrobenzonitrile
• CAS: 96336-91-3
• 化学式: C₉H₉N₃O₂
• 分子量: 191.189
• InChiKey: DRDILJFMVCWKPR-UHFFFAOYSA-N

物化性质

• 沸点：
  374.3±37.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-dimethylamino-2-nitrobenzonitrile 在 tin 作用下， 以 盐酸 、 二乙二醇二甲醚 为溶剂， 反应 3.33h， 生成 2,4-diamino-6-dimethylaminoquinazoline
  参考文献：
  名称：

  Antifolate and antibacterial activities of 6-substituted 2,4-diaminoquinazolines

  摘要：

  6-Substituted 2,4-diaminoquinazolines (1) are good inhibitors of dihydrofolate reductase (DHFR) and effective as growth inhibitors of intact bacterial cells in vitro. The most potent compounds in the in vitro tests were, however, ineffective against a systemic murine infection. Quantitative correlations were obtained between DHFR inhibition and the substituent constant molar refractivity (MR) for 3 of the 4 enzymes studied (Escherichia coli, Streptococcus faecalis, and bovine liver DHFR); for the fourth enzyme (Staphylococcus aureus DHFR) the best correlation was obtained with a combination of MR and the lipophilic parameter pi. The recognition that the conformational properties of the 6-substituent may play a vital role in mediating the binding of 1 to DHFR prompted the synthesis of novel analogues specifically designed to test this hypothesis. From these results it was possible to construct a simple schematic model of the binding site occupied by the 6-substituents; a subsequent molecular modelling study agreed with the features of this model.

  DOI：

  10.1016/0223-5234(92)90054-5
• 作为产物：
  描述：

  5-氯-2-硝基苯甲腈 在 二甲胺 作用下， 以 N-甲基乙酰胺 为溶剂， 生成 5-dimethylamino-2-nitrobenzonitrile
  参考文献：
  名称：

  Imidazoquinazolin-2-one compounds

  摘要：

  本发明揭示了具有抑制血小板聚集活性的咪唑喹唑啉-2-酮化合物。这些化合物具有高水溶性，对循环系统的影响较小，并且可用于治疗和预防血管内血栓栓塞和暂时性缺血，以及在使用假体装置时预防血栓形成。

  公开号：

  US04610987A1

文献信息

• Imidazoquinazolin-2-one compounds process for their production and pharmaceutical compositions containing said compounds
  申请人：DAIICHI SEIYAKU CO., LTD.

  公开号：EP0133234A2

  公开（公告）日：1985-02-20

  Imidazoquinazolin-2-one compounds having platelet aggregation inhibitory activity is disclosed. These compounds have high water-solubility and reduced influences on the circulatory system and are useful for treatment and prophylaxis of intravascular thromboembolism and temporary ischemia as well as prevention of thrombus upon use of prosthetic apparatus.

  本发明公开了具有血小板聚集抑制活性的咪唑喹唑啉-2-酮化合物。这些化合物具有很高的水溶性，对循环系统的影响较小，可用于治疗和预防血管内血栓栓塞和暂时性缺血，以及在使用假肢时防止血栓形成。
• US4610987A
  申请人：——

  公开号：US4610987A

  公开（公告）日：1986-09-09
• Antifolate and antibacterial activities of 6-substituted 2,4-diaminoquinazolines
  作者：NV Harris、C Smith、K Bowden

  DOI：10.1016/0223-5234(92)90054-5

  日期：1992.1

  6-Substituted 2,4-diaminoquinazolines (1) are good inhibitors of dihydrofolate reductase (DHFR) and effective as growth inhibitors of intact bacterial cells in vitro. The most potent compounds in the in vitro tests were, however, ineffective against a systemic murine infection. Quantitative correlations were obtained between DHFR inhibition and the substituent constant molar refractivity (MR) for 3 of the 4 enzymes studied (Escherichia coli, Streptococcus faecalis, and bovine liver DHFR); for the fourth enzyme (Staphylococcus aureus DHFR) the best correlation was obtained with a combination of MR and the lipophilic parameter pi. The recognition that the conformational properties of the 6-substituent may play a vital role in mediating the binding of 1 to DHFR prompted the synthesis of novel analogues specifically designed to test this hypothesis. From these results it was possible to construct a simple schematic model of the binding site occupied by the 6-substituents; a subsequent molecular modelling study agreed with the features of this model.
• Imidazoquinazolin-2-one compounds
  申请人：Daiichi Seiyaku Co., Ltd.

  公开号：US04610987A1

  公开（公告）日：1986-09-09

  Imidazoquinazolin-2-one compounds having platelet aggregation inhibitory activity is disclosed. These compounds have high water-solubility and reduced influences on the circulatory system and are useful for treatment and prophylaxis of intravascular thromboembolism and temporary ischemia as well as prevention of thrombus upon use of prosthetic apparatus.

  本发明揭示了具有抑制血小板聚集活性的咪唑喹唑啉-2-酮化合物。这些化合物具有高水溶性，对循环系统的影响较小，并且可用于治疗和预防血管内血栓栓塞和暂时性缺血，以及在使用假体装置时预防血栓形成。