3-氨基-4-硝基-4'-氟二苯甲酮 | 180601-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氨基-4-硝基-4'-氟二苯甲酮
• 英文名称: 3-Amino-4-nitro-4'-fluorobenzophenone
• 英文别名: (3-amino-4-nitrophenyl)-(4-fluorophenyl)methanone
• CAS: 180601-52-9
• 化学式: C₁₃H₉FN₂O₃
• 分子量: 260.224
• InChiKey: PMYOTRXHOODHIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  478.3±45.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 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：
  88.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氨基-4-硝基-4'-氟二苯甲酮 在 镍 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (3,4-二氨基苯)(4-氟苯)甲酮
  参考文献：
  名称：

  Antirhino/Enteroviral Vinylacetylene Benzimidazoles:  A Study of Their Activity and Oral Plasma Levels in Mice

  摘要：

  In an effort to find an orally bioavailable antiviral for the treatment of rhino/enteroviral infections, a series of vinylacetylene benzimidazoles (11a-o, 12, and 18a was made. Initial studies of this class of antivirals showed that fluorine substitution on the left-hand phenyl ring in combination with the vinylacetylene moiety gave the requisite mix of physical properties to achieve good in vitro antiviral activity as well as respectable oral bioavailability in rhesus monkeys. To ascertain the generality of this finding and to broaden the scope of the structure-activity relationship (SAR), the present study concentrated on fluoro substitution of this class of molecules. The initial antiviral activity for each analogue was measured using human rhinovirus 14 (HRV-14). This served as an indicator of general antiviral activity for SAR purposes. Subsequently, the spectrum of antirhino/enteroviral activity of the more interesting analogues was evaluated through testing against a panel of seven additional rhino/enteroviruses. Broad-spectrum activity was present and consistent for all analogues tested, and it tracked closely with the antiviral activity observed against HRV-14. A simple screening protocol for oral bioavailability was established whereby compounds were administered orally to mice and plasma levels were measured. This procedure facilitated the evaluation of numerous analogues in a rapid manner. The C-max was used as a measure of oral bioavailability to allow relative ranking of compounds. In general, fluorine substitution directly on the left-hand aromatic ring does give good oral blood levels. However, fluorine incorporation at other positions in the molecule was not as effective at maintaining either the activity or the oral plasma levels. The constructive combination of activity and oral plasma levels was maximized in three derivatives: 11a,e,g.

  DOI：

  10.1021/jm970423k
• 作为产物：
  描述：

  2-硝基-5-氯苯胺 在 potassium tert-butylate 、 双氧水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-氨基-4-硝基-4'-氟二苯甲酮
  参考文献：
  名称：

  Antirhino/Enteroviral Vinylacetylene Benzimidazoles:  A Study of Their Activity and Oral Plasma Levels in Mice

  摘要：

  In an effort to find an orally bioavailable antiviral for the treatment of rhino/enteroviral infections, a series of vinylacetylene benzimidazoles (11a-o, 12, and 18a was made. Initial studies of this class of antivirals showed that fluorine substitution on the left-hand phenyl ring in combination with the vinylacetylene moiety gave the requisite mix of physical properties to achieve good in vitro antiviral activity as well as respectable oral bioavailability in rhesus monkeys. To ascertain the generality of this finding and to broaden the scope of the structure-activity relationship (SAR), the present study concentrated on fluoro substitution of this class of molecules. The initial antiviral activity for each analogue was measured using human rhinovirus 14 (HRV-14). This served as an indicator of general antiviral activity for SAR purposes. Subsequently, the spectrum of antirhino/enteroviral activity of the more interesting analogues was evaluated through testing against a panel of seven additional rhino/enteroviruses. Broad-spectrum activity was present and consistent for all analogues tested, and it tracked closely with the antiviral activity observed against HRV-14. A simple screening protocol for oral bioavailability was established whereby compounds were administered orally to mice and plasma levels were measured. This procedure facilitated the evaluation of numerous analogues in a rapid manner. The C-max was used as a measure of oral bioavailability to allow relative ranking of compounds. In general, fluorine substitution directly on the left-hand aromatic ring does give good oral blood levels. However, fluorine incorporation at other positions in the molecule was not as effective at maintaining either the activity or the oral plasma levels. The constructive combination of activity and oral plasma levels was maximized in three derivatives: 11a,e,g.

  DOI：

  10.1021/jm970423k

文献信息

• Anti-viral compounds
  申请人：Eli Lilly and Company

  公开号：US05693661A1

  公开（公告）日：1997-12-02

  Certain vinyl acetylene benzimidazole compounds which inhibit the growth of picornaviruses, such as rhinoviruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus.

  某些乙烯基苯并咪唑化合物可以抑制小肠病毒，如鼻病毒、肠病毒、心肌病毒、脊髓灰质炎病毒、A组和B组柯萨奇病毒、回声病毒和门戈病毒的生长。
• Anti-viral compound
  申请人：Eli Lilly and Company

  公开号：US05891874A1

  公开（公告）日：1999-04-06

  A series of benzimidazole compounds having the following general structure are provided which inhibit the growth of picornaviruses (e.g., rhinoviruses, enteroviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus) and flaviviruses (e.g., hepatitis C and bovine diarrheal virus). ##STR1## A method for inhibiting picornaviruses and flaviviruses is also provided which includes administering to a host an effective amount of the inventive benzimidazole compounds.

  提供了一系列具有以下一般结构的苯并咪唑化合物，其抑制小肠病毒（例如，鼻病毒，肠病毒，脊髓灰质炎病毒，A和B组的柯萨奇病毒，回声病毒和门戈病毒）和黄病毒（例如，丙型肝炎和牛痢疾病毒）的生长。##STR1## 还提供了一种抑制小肠病毒和黄病毒的方法，包括向宿主施加创新苯并咪唑化合物的有效量。
• Anti-viral benzimidazole derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0747363A1

  公开（公告）日：1996-12-11

  Certain vinyl acetylene benzimidazole compounds of the formula I which inhibit the growth of picornaviruses, such as rhinoviruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus.

  某些式 I 的乙烯基乙炔苯并咪唑化合物 可抑制鼻病毒、肠病毒、心病毒、脊髓灰质炎病毒、A 和 B 组柯萨奇病毒、回声病毒和门戈病毒等皮卡病毒的生长。
• ANTI-VIRAL COMPOUNDS
  申请人：ELI LILLY AND COMPANY

  公开号：EP0862430A1

  公开（公告）日：1998-09-09
• EP0862430A4
  申请人：——

  公开号：EP0862430A4

  公开（公告）日：1999-03-24