N-(3,5-二氟苄基)-2-硝基苯胺 | 105969-13-9

• 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: N-(3,5-二氟苄基)-2-硝基苯胺
• 英文名称: N-(3,5-difluorobenzyl)-2-nitroaniline
• 英文别名: N-[(3,5-difluorophenyl)methyl]-2-nitroaniline
• CAS: 105969-13-9
• 化学式: C₁₃H₁₀F₂N₂O₂
• 分子量: 264.231
• InChiKey: BKMRQGAQVCOMNP-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  371.3±37.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 N-(3,5-二氟苄基)-2-硝基苯胺 在 platinum(IV) oxide 氢氧化钾 、 氢气 作用下， 生成 1-(3,5-二氟苄基)苯并咪唑-2-硫酮
  参考文献：
  名称：

  Some benzyl-substituted imidazoles, triazoles, tetrazoles, pyridinethiones, and structural relatives as multisubstrate inhibitors of dopamine .beta.-hydroxylase. 4. Structure-activity relationships at the copper binding site

  摘要：

  Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor. Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously. The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity. An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitory potency. In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced. Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.

  DOI：

  10.1021/jm00164a051
• 作为产物：
  描述：

  3,5-二氟苯甲腈 在 镍 乙酸铵 、 氨 、 氢气 作用下， 以 甲醇 为溶剂， 100.0 ℃ 、344.73 kPa 条件下， 反应 25.5h， 生成 N-(3,5-二氟苄基)-2-硝基苯胺
  参考文献：
  名称：

  Some benzyl-substituted imidazoles, triazoles, tetrazoles, pyridinethiones, and structural relatives as multisubstrate inhibitors of dopamine .beta.-hydroxylase. 4. Structure-activity relationships at the copper binding site

  摘要：

  Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor. Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously. The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity. An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitory potency. In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced. Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.

  DOI：

  10.1021/jm00164a051

文献信息

• 1-substituted-2-mercapto benzimidazole compounds and intermediates
  申请人：SmithKline Beckman Corporation

  公开号：US04728741A1

  公开（公告）日：1988-03-01

  1-substituted-2-mercapto(or aminomethyl)benzimidazole compounds of the formula ##STR1## inhibit dopamine-.beta.-hydroxylase activity. Intermediates are also disclosed.

  1-取代-2-巯基（或氨甲基）苯并咪唑化合物的化学式为##STR1##，能抑制多巴胺-β-羟化酶活性。中间体也被披露。
• Dopamine-.beta.-hydroxylase inhibitors
  申请人：SmithKline Beckman Corporation

  公开号：US04857540A1

  公开（公告）日：1989-08-15

  1-substituted-2-mercapto(or aminomethyl)benzimidazole compounds which inhibit dopamine-.beta.-hydroxylase activity.

  这句话的中文翻译如下：抑制多巴胺-β-羟化酶活性的1-取代-2-巯基（或氨甲基）苯并咪唑化合物。
• Dopamine-beta-hydroxylase inhibitors
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0190817A1

  公开（公告）日：1986-08-13

  Compounds of structure in which Y is -CH2NH2 or SR; R is hydrogen or C1-4 alkyl; n is 0 to 5; and R2 to R6 are the same or different and are each hydrogen, halogen, hydroxy, C1-4 alkyl, CN, N02, SO2NH2, CO2H, CONH2, CHO, CH2OH, CF3, C1-4 alkoxy, SO2C1-4 fluoroalkyl or CO2C1-4 alkyl; processes for their preparation, pharmaceutical compositions containing them and their use in therapy, for example, as anti-hypertensive agents.

  Y为-CH2NH2或SR；R为氢或C1-4烷基；n为0至5；R2至R6为相同或不同且各自为氢、卤素、羟基、C1-4烷基、CN、N02、SO2NH2、CO2H、CONH2、CHO、CH2OH、CF3、C1-4烷氧基、SO2C1-4氟烷基或CO2C1-4烷基的结构化合物；其制备工艺、含有它们的药物组合物及其在治疗中的用途，例如用作抗高血压剂。
• KAISER, CARL;KRUSE, LAWRENCE I.
  作者：KAISER, CARL、KRUSE, LAWRENCE I.

  DOI：——

  日期：——
• US4728741A
  申请人：——

  公开号：US4728741A

  公开（公告）日：1988-03-01