4-硝基-N-[2-(4-硝基苯氧基)乙基]苯乙胺 | 226992-13-8

• 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: 4-硝基-N-[2-(4-硝基苯氧基)乙基]苯乙胺
• 英文名称: N-[2-(p-nitrophenoxy)ethyl]-p-nitrophenethylamine
• 英文别名: [2-(4-nitrophenyl)ethyl]{2-[(4-nitrophenyl)oxy]ethyl}amine；N-2-(4-nitrophenyl)ethyl-N-(2-(4-nitrophenoxy)ethyl)amine；2-(4-nitrophenoxy)-N-[2-(4-nitrophenyl)ethyl]ethanamine；N-[2-(4-nitrophenoxy)ethyl]-2-(4-nitrophenyl)ethanamine
• CAS: 226992-13-8
• 化学式: C₁₆H₁₇N₃O₅
• 分子量: 331.328
• InChiKey: MYUWQXUKSBKSDS-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  520.5±40.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  4-硝基-N-[2-(4-硝基苯氧基)乙基]苯乙胺 在 盐酸 、 ammonium chloride 、 铁粉 、 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 4-[2-[2-(4-Aminophenoxy)ethyl-[(4-chlorophenyl)methyl]amino]ethyl]aniline
  参考文献：
  名称：

  New p-Methylsulfonamido Phenylethylamine Analogues as Class III Antiarrhythmic Agents:  Design, Synthesis, Biological Assay, and 3D-QSAR Analysis

  摘要：

  Class III antiarrhythmic agents selectively delay the effective refractory period (ERP) and increase the transmembrance action potential duration (APD). Using dofetilide (2) as a template of class III antiarrhythmic agents, we designed and synthesized 16 methylsulfonamido phenylethylamine analogues (4a-d and 5a-1). Pharmacological assay indicated that all of these compounds showed activity for increasing the ERP in isolated animal atrium; among them, the effective concentration of compound 4a is 1.6 x 10(-8) mol/L in increasing ERP by 10 ms, slightly less potent than that of 2, 1.1 x 10(-8) mol/L. Compound 4a also produced a slightly lower change in ERP at 10(-5) M, DeltaERP% = 17.5% (DeltaERP% = 24.0% for dofetilide). On the basis of this bioassay result, these 16 compounds together with dofetilide were investigated by the three-dimensional quantitative structure-activity relationship (3D-QSAR) techniques of comparative molecular field analysis (CoMFA), comparative molecular similarity index analysis (CoMSIA), and the hologram QSAR (HQSAR). The 3D-QSAR models were tested with another 11 compounds (4e-h and 5m-s) that we synthesized later. Results revealed that the CoMFA, CoMSIA, and HQSAR predicted activities for the 11 newly synthesized compounds that have a good correlation with their experimental value, r(2) = 0.943, 0.891, and 0.809 for the three QSAR models, respectively. This indicates that the 3D-QSAR models proved a good predictive ability and could describe the steric, electrostatic, and hydrophobic requirements for recognition forces of the receptor site. On the basis of these results, we designed and synthesized another eight new analogues of methanesulfonamido phenylethyamine (6a-h) according to the clues provided by the 3D-QSAR analyses. Pharmacological assay indicated that the effective concentrations of delaying the ERP by 10 ins of these newly designed compounds correlated well with the 3D-QSAR predicted values. It is remarkable that the percent change of delaying ERP at 10-5 M compound 6c is much higher than that of dofetilide; the effective concentration of compound 6c is 5.0 x 10(-8)mol/L in increasing the ERP by 10 Ms, which is slightly lower than that of 2. The results showed that the 3D-QSAR models are reliable and can be extended to design new antiarrhythmic agents.

  DOI：

  10.1021/jm010574u
• 作为产物：
  描述：

  N-(4-硝基苯乙基)乙酰胺 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 4-硝基-N-[2-(4-硝基苯氧基)乙基]苯乙胺
  参考文献：
  名称：

  New p-Methylsulfonamido Phenylethylamine Analogues as Class III Antiarrhythmic Agents:  Design, Synthesis, Biological Assay, and 3D-QSAR Analysis

  摘要：

  Class III antiarrhythmic agents selectively delay the effective refractory period (ERP) and increase the transmembrance action potential duration (APD). Using dofetilide (2) as a template of class III antiarrhythmic agents, we designed and synthesized 16 methylsulfonamido phenylethylamine analogues (4a-d and 5a-1). Pharmacological assay indicated that all of these compounds showed activity for increasing the ERP in isolated animal atrium; among them, the effective concentration of compound 4a is 1.6 x 10(-8) mol/L in increasing ERP by 10 ms, slightly less potent than that of 2, 1.1 x 10(-8) mol/L. Compound 4a also produced a slightly lower change in ERP at 10(-5) M, DeltaERP% = 17.5% (DeltaERP% = 24.0% for dofetilide). On the basis of this bioassay result, these 16 compounds together with dofetilide were investigated by the three-dimensional quantitative structure-activity relationship (3D-QSAR) techniques of comparative molecular field analysis (CoMFA), comparative molecular similarity index analysis (CoMSIA), and the hologram QSAR (HQSAR). The 3D-QSAR models were tested with another 11 compounds (4e-h and 5m-s) that we synthesized later. Results revealed that the CoMFA, CoMSIA, and HQSAR predicted activities for the 11 newly synthesized compounds that have a good correlation with their experimental value, r(2) = 0.943, 0.891, and 0.809 for the three QSAR models, respectively. This indicates that the 3D-QSAR models proved a good predictive ability and could describe the steric, electrostatic, and hydrophobic requirements for recognition forces of the receptor site. On the basis of these results, we designed and synthesized another eight new analogues of methanesulfonamido phenylethyamine (6a-h) according to the clues provided by the 3D-QSAR analyses. Pharmacological assay indicated that the effective concentrations of delaying the ERP by 10 ins of these newly designed compounds correlated well with the 3D-QSAR predicted values. It is remarkable that the percent change of delaying ERP at 10-5 M compound 6c is much higher than that of dofetilide; the effective concentration of compound 6c is 5.0 x 10(-8)mol/L in increasing the ERP by 10 Ms, which is slightly lower than that of 2. The results showed that the 3D-QSAR models are reliable and can be extended to design new antiarrhythmic agents.

  DOI：

  10.1021/jm010574u

文献信息

• NOVEL DIAMINE, POLYAMIC ACID, AND POLYIMIDE
  申请人：NISSAN CHEMICAL INDUSTRIES. LTD.

  公开号：US20160264520A1

  公开（公告）日：2016-09-15

  To provide a novel diamine, and a polyimide precursor and a polyimide using it. A diamine represented by the formula (1): wherein each of X 1 and X 5 which are independent of each other, is a single bond or the like; each of X 2 and X 4 which are independent of each other, is —CH 2 — or the like; X 3 is a C 1-6 alkylene or the like; each of Y 1 and Y 2 which are independent of each other, is a single bond or the like; R is a C 1-20 linear, branched or cyclic hydrocarbon group; and a is 0 or 1).

  提供一种新颖的二胺，以及使用它的聚酰亚胺前体和聚酰亚胺。一种由式（1）表示的二胺：其中X1和X5中的每一个独立的，是单键或类似物；X2和X4中的每一个独立的，是—CH2—或类似物；X3是C1-6烷基或类似物；Y1和Y2中的每一个独立的，是单键或类似物；R是C1-20线性、支链或环烃基；a为0或1。
• [EN] 7-(1H-PYRAZOL-4-YL)-1,6-NAPHTHYRIDINE COMPOUNDS AS SYK INHIBITORS<br/>[FR] COMPOSÉS DE 7-(1H-PYRAZOL-4-YL)-1,6-NAPHTYRIDINE COMME INHIBITEURS DE SYK
  申请人：GLAXO GROUP LTD

  公开号：WO2011134971A1

  公开（公告）日：2011-11-03

  A compound of formula (I) or a salt thereof; which is an inhibitor of spleen tyrosine kinase (Syk) and therefore potentially of use in treating diseases resulting from inappropriate activation of mast and/or basophil cells, macrophages, and B-cells and related inflammatory responses and tissue damage, for instance inflammatory disease and/or allergic disorders, and in cancer therapy, specifically heme malignancies, chronic spontaneous urticaria and autoimmune conditions.

  化合物的化学式（I）或其盐；它是脾酪氨酸激酶（Syk）的抑制剂，因此可能用于治疗由于肥大细胞和/或嗜碱细胞、巨噬细胞和B细胞的不适当激活而导致的疾病，以及相关的炎症反应和组织损伤，例如炎症性疾病和/或过敏性疾病，以及癌症治疗，特别是血液恶性肿瘤、慢性自发性荨麻疹和自身免疫疾病。
• 7-(lH-PYRAZOL-4-YL)-1,6-NAPHTHYRIDINE COMPOUNDS AS SYK INHIBITORS
  申请人：Atkinson Francis Louis

  公开号：US20130040984A1

  公开（公告）日：2013-02-14

  The present invention relates to a compound of formula (I): or a salt thereof; which is an inhibitor of spleen tyrosine kinase (Syk) and therefore potentially of use in treating diseases resulting from inappropriate activation of mast and/or basophil cells, macrophages, and B-cells and related inflammatory responses and tissue damage, for instance inflammatory disease and/or allergic disorders, and in cancer therapy, specifically heme malignancies, chronic spontaneous urticaria and autoimmune conditions.

  本发明涉及化合物的结构式(I)：或其盐；该化合物是脾酪氨酸激酶（Syk）的抑制剂，因此可能用于治疗由于肥大细胞和/或嗜碱性粒细胞、巨噬细胞和B细胞不适当激活引起的疾病，以及相关的炎症反应和组织损伤，例如炎症性疾病和/或过敏性疾病，以及癌症治疗，特别是血液恶性肿瘤、慢性自发性荨麻疹和自身免疫疾病。
• [EN] PYRIMIDINECARBOXAMIDE DERIVATIVES AS INHIBITORS OF SYK KINASE<br/>[FR] DÉRIVÉS DE PYRIMIDINE CARBOXAMIDE COMME INHIBITEURS DE LA KINASE SYK
  申请人：GLAXO GROUP LTD

  公开号：WO2010097248A1

  公开（公告）日：2010-09-02

  The compound of formula (I) or a salt, preferably a pharmaceutically acceptable salt, thereof; is an inhibitor of spleen tyrosine kinase (SYK) and therefore potentially of use in treating diseases resulting from inappropriate mast cell activation, for instance allergic and inflammatory diseases, as well of potential use in cancer therapy, specifically heme malignancies.

  化合物式(I)或其盐，最好是药学上可接受的盐；是脾酪氨酸激酶（SYK）的抑制剂，因此可能用于治疗由于不适当的肥大细胞激活引起的疾病，例如过敏和炎症性疾病，也可能用于癌症治疗，特别是血红素恶性肿瘤。
• 7-(1H-pyrazol-4-yl)-1,6-naphthyridine compounds as Syk inhibitors
  申请人：Atkinson Francis Louis

  公开号：US08633319B2

  公开（公告）日：2014-01-21

  The present invention relates to a compound of formula (I): or a salt thereof; which is an inhibitor of spleen tyrosine kinase (Syk) and therefore potentially of use in treating diseases resulting from inappropriate activation of mast and/or basophil cells, macrophages, and B-cells and related inflammatory responses and tissue damage, for instance inflammatory disease and/or allergic disorders, and in cancer therapy, specifically heme malignancies, chronic spontaneous urticaria and autoimmune conditions.

  本发明涉及一种公式(I)的化合物或其盐；该化合物是脾酪氨酸激酶（Syk）的抑制剂，因此可能用于治疗由于肥大细胞和/或嗜碱性粒细胞、巨噬细胞和B细胞的不适当激活引起的疾病，以及相关的炎症反应和组织损伤，例如炎症性疾病和/或过敏性疾病，并且在癌症治疗中，特别是血红素恶性肿瘤、慢性自发性荨麻疹和自身免疫疾病方面。