2,4-dichloro-N-hydroxybenzenecarboximidoyl azide | 293314-15-5

• 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: 2,4-dichloro-N-hydroxybenzenecarboximidoyl azide
• CAS: 293314-15-5
• 化学式: C₇H₄Cl₂N₄O
• 分子量: 231.041
• InChiKey: MSOFQXZHBACMQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-N-hydroxybenzenecarboximidoyl azide 以 乙醇 、 乙腈 为溶剂， 反应 12.0h， 生成 5-(2,4-dichlorophenyl)-1H-tetrazol-1-ol
  参考文献：
  名称：

  Azide Oximes and 1-Hydroxytetrazoles

  摘要：

  Eleven azide oximes were prepared and tested for their antiplatelet (in vitro), antithrombotic, and blood pressure lowering activities. Nine of them inhibited the aggregation of blood platelets (Born test, inducer collagen) with IC50 values between 10 and 50 microM. The most active compounds i.e. azido-4-nitrophenylbenzaldoxime (2h) had an IC50 = 2 microM. Nine azide oximes exhibited significant antithrombotic properties. The most active compounds were 2h and 2c (azido-4-methylphenylbenzaldoxime) with an inhibition of thrombus formation above 20% in arterioles after a single p.o. dose of 60 mg/kg. Both compounds lowered the blood pressure in spontaneously hypertensive rats by 11% (2h) or 5% (2c), respectively. Seven azide oximes were rearranged to the title tetrazololes which however showed smaller antithrombotic effects. In separate in vitro experiments at 37 degrees C it could be demonstrated that azide oximes release nitric oxide (conversion rate approximately 10%.h-1) and nitrosohydrogen (conversion rate approximately 2%.h-1). This makes it appear probable that the above effects are mediated by these molecules.

  DOI：

  10.1002/1521-4184(20006)333:6<157::aid-ardp157>3.0.co;2-c
• 作为产物：
  描述：

  2,4-二氯-N-羟基苯甲酰氯 在 sodium azide 作用下， 以 甲醇 为溶剂， 以97%的产率得到2,4-dichloro-N-hydroxybenzenecarboximidoyl azide
  参考文献：
  名称：

  Azide Oximes and 1-Hydroxytetrazoles

  摘要：

  Eleven azide oximes were prepared and tested for their antiplatelet (in vitro), antithrombotic, and blood pressure lowering activities. Nine of them inhibited the aggregation of blood platelets (Born test, inducer collagen) with IC50 values between 10 and 50 microM. The most active compounds i.e. azido-4-nitrophenylbenzaldoxime (2h) had an IC50 = 2 microM. Nine azide oximes exhibited significant antithrombotic properties. The most active compounds were 2h and 2c (azido-4-methylphenylbenzaldoxime) with an inhibition of thrombus formation above 20% in arterioles after a single p.o. dose of 60 mg/kg. Both compounds lowered the blood pressure in spontaneously hypertensive rats by 11% (2h) or 5% (2c), respectively. Seven azide oximes were rearranged to the title tetrazololes which however showed smaller antithrombotic effects. In separate in vitro experiments at 37 degrees C it could be demonstrated that azide oximes release nitric oxide (conversion rate approximately 10%.h-1) and nitrosohydrogen (conversion rate approximately 2%.h-1). This makes it appear probable that the above effects are mediated by these molecules.

  DOI：

  10.1002/1521-4184(20006)333:6<157::aid-ardp157>3.0.co;2-c

文献信息

• Azide Oximes and 1-Hydroxytetrazoles
  作者：Klaus Rehse、Franziska Brehme

  DOI：10.1002/1521-4184(20006)333:6<157::aid-ardp157>3.0.co;2-c

  日期：2000.6

  Eleven azide oximes were prepared and tested for their antiplatelet (in vitro), antithrombotic, and blood pressure lowering activities. Nine of them inhibited the aggregation of blood platelets (Born test, inducer collagen) with IC50 values between 10 and 50 microM. The most active compounds i.e. azido-4-nitrophenylbenzaldoxime (2h) had an IC50 = 2 microM. Nine azide oximes exhibited significant antithrombotic properties. The most active compounds were 2h and 2c (azido-4-methylphenylbenzaldoxime) with an inhibition of thrombus formation above 20% in arterioles after a single p.o. dose of 60 mg/kg. Both compounds lowered the blood pressure in spontaneously hypertensive rats by 11% (2h) or 5% (2c), respectively. Seven azide oximes were rearranged to the title tetrazololes which however showed smaller antithrombotic effects. In separate in vitro experiments at 37 degrees C it could be demonstrated that azide oximes release nitric oxide (conversion rate approximately 10%.h-1) and nitrosohydrogen (conversion rate approximately 2%.h-1). This makes it appear probable that the above effects are mediated by these molecules.
• 1-Benzyloxy-5-phenyltetrazole derivatives highly active against androgen receptor-dependent prostate cancer cells
  作者：Shiting Zhao、Abdelsalam S. Ali、Xinyu Kong、Yan Zhang、Xiaomin Liu、Melissa A. Skidmore、Craig M. Forsyth、G. Paul Savage、Donghai Wu、Yong Xu、Craig L. Francis

  DOI：10.1016/j.ejmech.2022.114982

  日期：2023.1