N-(2-benzoyl-4-nitrophenyl)trifluoroacetamide | 313499-48-8

• 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: N-(2-benzoyl-4-nitrophenyl)trifluoroacetamide
• 英文别名: 2-(Trifluoroacetylamino)-5-nitrobenzophenone；N-(2-benzoyl-4-nitrophenyl)-2,2,2-trifluoroacetamide
• CAS: 313499-48-8
• 化学式: C₁₅H₉F₃N₂O₄
• 分子量: 338.243
• InChiKey: WNQZSRLLAVNFKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  503.6±50.0 °C(Predicted)
• 密度：
  1.477±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(2-benzoyl-4-nitrophenyl)trifluoroacetamide 在 吡啶 、 potassium carbonate 、 tin(ll) chloride 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 甲苯 为溶剂， 反应 9.5h， 生成 (E)-(R)-N-[2-benzoyl-4-{3-[5-(4-nitrophenyl)-2-furyl]acryloyl-amino}phenyl]-N-tert-butoxycarbonyphenylalanine amide
  参考文献：
  名称：

  Structure–Activity relationships of novel anti-malarial agents. Part 6: N-(4-Arylpropionylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides

  摘要：

  We have demonstrated that the p-trifluoromethylphenylpropionylamino residue at the 2-position of the core structure leads to an active benzophenone-type anti-malarial agent. The attempt to improve water solubility by introduction of an amino group into the alpha-position of the arylpropionyl residue resulted in decreased activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00179-3
• 作为产物：
  描述：

  2,2,2-三氟乙酰胺 、 2-氨基-5-硝基二苯甲酮 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(2-benzoyl-4-nitrophenyl)trifluoroacetamide
  参考文献：
  名称：

  非硫醇法呢基转移酶抑制剂：N-（4-氨基酰基氨基-3-苯甲酰基苯基）-3- [5-（4-硝基苯基）-2呋喃基]丙烯酸酰胺及其抗疟活性。

  摘要：

  先前发现水溶性对于新型基于二苯甲酮的法呢基转移酶抑制剂的体内抗动物活动是必不可少的。在苯乙酸亚结构中引入α-氨基可提供具有较高法呢基转移酶抑制活性的更可溶化合物。这种结构修饰不利地影响了体外抗动物活动。

  DOI：

  10.1016/j.ejmech.2004.09.019

文献信息

• Non-thiol Farnesyltransferase Inhibitors: N-(4-Acylamino-3-benzoylphenyl)-4-nitrocinnamic Acid Amides
  作者：Jacek Sakowski、Isabel Sattler、Martin Schlitzer

  DOI：10.1016/s0968-0896(01)00274-7

  日期：2002.2

  novel non-thiol farnesyltransferase inhibitor. Replacement of the p-tolyl moiety of our initial lead structure 4a by different para and ortho substituted phenyl residues as well as by 1-naphthyl resulted in derivatives with considerably enhanced activity displaying IC(50) values between 42 and 52 nM. These compounds represent novel, readily accessible non-thiol farnesyltransferase inhibitors being

  我们已经开发了4-硝基肉桂酰基取代的二苯甲酮4a作为新型的非硫醇法呢基转移酶抑制剂。用不同的对位和邻位取代的苯基残基以及1-萘基取代我们最初的铅结构4a的对甲苯基部分，得到的衍生物具有显着增强的活性，显示的IC（50）值为42至52 nM。这些化合物代表了新颖的，易于获得的非硫醇法尼基转移酶抑制剂，其活性高于相应的含硫醇类似物。
• Use of 2-phenylene diamine derivatives for the treatment of infections
  申请人：——

  公开号：US20030036532A1

  公开（公告）日：2003-02-20

  The invention relates to the use of compounds of formula (I), wherein n=0-3; R 1 , R 2 =H, alkyl, aryl, heteroaryl, acyl; R 3 =H, halogen, alkyl, aryl, heteroaryl, arylalkyl, acyl, CN, NO 2 , R 4 —X—; R 4 =H, alkyl, aryl, heteroaryl, aralkyl, acyl; X=NH, O, S, SO 2 , NHSO 2 , OSO 2 , and A, B, C=organic groups. The inventive compounds are used for the prophylaxis and the therapeutic treatment of infectious processes, especially of infectious processes caused by parasites. The invention further relates to medicaments that contain the inventive compounds.

  该发明涉及使用式(I)的化合物，其中n=0-3；R1、R2=H、烷基、芳基、杂环芳基、酰基；R3=H、卤素、烷基、芳基、杂环芳基、芳基烷基、酰基、CN、NO2、R4—X—；R4=H、烷基、芳基、杂环芳基、芳基烷基、酰基；X=NH、O、S、SO2、NHSO2、OSO2，以及A、B、C=有机基团。这些新颖化合物可用于预防和治疗感染过程，特别是由寄生虫引起的感染过程。该发明还涉及含有这些新颖化合物的药物。
• Synthesis, Molecular Modeling, and Structure−Activity Relationship of Benzophenone-Based CAAX-Peptidomimetic Farnesyltransferase Inhibitors
  作者：Jacek Sakowski、Markus Böhm、Isabel Sattler、Hans-Martin Dahse、Martin Schlitzer

  DOI：10.1021/jm010872r

  日期：2001.8.1

  Because of the involvement of farnesylated proteins in oncogenesis, inhibition of the protein-modifying enzyme farnesyltransferase is considered a major emerging strategy in cancer therapy. Here, we describe the structure-activity relationship of a novel class of CAAX-peptidomimetic farnesyltransferase inhibitors based on the benzophenone scaffold. 4 ' -Methyl, 4 ' -chloro, 4 ' -bromo, and 4 ' -nitrophenylacetic acid as substituents at the 2-amino group of the benzophenone core structure yield farnesyltransferase inhibitors active in the nanomolar range. Using diphenylacetic acid in this position further improves activity. SEAL superimposition of inhibitor 12a to the enzyme-bound conformation of a CAAX-peptide shows a markedly good resemblance of the molecular properties of the peptide. FlexX docking of 12a confirms the good fit of the molecule into the peptide binding site of farnesyltransferase. The novel benzophenone-based AAX-peptidomimetic substructure described here will be useful for the design of some novel types of farnesyltransferase inhibitors.
• Structure–Activity Relationships of Novel Anti-Malarial Agents. Part 3: N-(4-Acylamino-3-benzoylphenyl)-4-propoxycinnamic Acid Amides
  作者：Jochen Wiesner、Katja Kettler、Hassan Jomaa、Martin Schlitzer

  DOI：10.1016/s0960-894x(01)00798-3

  日期：2002.2

  We have described 5-(4-propoxycinnamoylamino)-2-(4-tolylacetylamino)benzophenone 6e as a novel lead for antimalarial agents. Anti-malarial activity of these 5-(4-propoxycinnamoylamino)benzophenones proved to be quite sensitive against variations of the acyl substituent at the 2-amino group. Best activity was obtained with phenylacetic acid moieties carrying small substituents in the para-position. From the para-substituents evaluated, the trifluoromethyl group yielded the most active compound (6j) in this series (IC50 = 120 nM). Deviations from the phenylacetic acid substructure, shifting the substituent into the ortho-position or bulkier para-substituents resulted in a significant reduction in anti-malarial activity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Palladium-Catalyzed Tandem Intramolecular Oxy/Amino-Palladation/Isocyanide Insertion: Synthesis of α-Benzofuranyl/Indolylacetamides
  作者：Nuligonda Thirupathi、Madala Hari Babu、Vikas Dwivedi、Ruchir Kant、Maddi Sridhar Reddy

  DOI：10.1021/ol501048x

  日期：2014.6.6

  A novel palladium-catalyzed approach to 2-benzofuranyl/indolylacetamides from 1-(o-hydroxy/aminophenyl)propargylic alcohols and isocyanides is described. The reaction proceeds through a cascade that includes oxy/aminopalladation, isocyanide insertion, and 1,4-hydroxyl migration. No oxidant or ligand is needed to promote the cascade, and the reactions are carried out under mild conditions to afford the products through high functional tolerance.