N-trifluoroacetic-3-nitroaniline | 25080-83-5

• 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: N-trifluoroacetic-3-nitroaniline
• 英文别名: 3-nitrotrifluoroacetanilide；m-nitrotrifluoroacetanilide；2,2,2-Trifluor-N-(3'-nitrophenyl)-acetamid；N-m-Nitrophenyltrifluoracetamid；3-Nitrophenyl-trifluoracetamid；m-Nitrotrifluoracetoacetanilid；2,2,2-trifluoro-N-(3-nitrophenyl)acetamide
• CAS: 25080-83-5
• 化学式: C₈H₅F₃N₂O₃
• mdl: MFCD00452601
• 分子量: 234.135
• InChiKey: ODXWGMFPJCIUCW-UHFFFAOYSA-N

物化性质

• 保留指数：
  1522

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-trifluoroacetic-3-nitroaniline 在 镍 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 、 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 10.0h， 生成 m(Ac-L-Asp-L-Val-NH)-N-phenylglycine
  参考文献：
  名称：

  N-Nitrosoanilines: a new class of caspase-3 inhibitors

  摘要：

  Caspases are a family of cysteine proteases activated during apoptosis. In cultured human endothelial cells, physiological levels of NO prevent apoptosis and interfere with the activation of the caspase cascade. Previous studies have demonstrated that NO inhibits the activity of caspase-3 by S-nitrosylation of the enzyme. In this study, the inhibitory effect of a new class of NO donors, N-nitrosoaniline derivatives, were examined against caspase-3. Initially eight small molecule inhibitors bearing N-nitroso moieties were assayed. It was found that the presence of an electron-donating group on the phenyl ring led to better inhibitory potency, a trend consistent with the results from the previous papain studies. Based on the analysis of the enzyme and substrates' structures, two peptidyl N-nitrosoaniline inhibitors [Ac-DVAD-NNO (1) and Ac-DV-AMO (2)] were designed and synthesized. Both compounds exhibited enhanced inhibitory potency against caspase-3. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00222-4
• 作为产物：
  描述：

  间硝基苯胺 、 三氟乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到N-trifluoroacetic-3-nitroaniline
  参考文献：
  名称：

  Inhibitors of IMPDH enzyme

  摘要：

  本发明涉及一类新型的IMPDH抑制剂化合物。该发明还涉及包含这些化合物的药物组合物。本发明的化合物和药物组合物特别适用于抑制IMPDH酶活性，因此可以优势地用作IMPDH介导的过程的治疗剂。本发明还涉及使用本发明的化合物和相关化合物抑制IMPDH活性的方法。

  公开号：

  US06344465B1

文献信息

• A one-pot procedure for trifluoroacetylation of arylamines using trifluoroacetic acid as a trifluoroacetylating reagent
  作者：Junpei Ohtaka、Takeshi Sakamoto、Yasuo Kikugawa

  DOI：10.1016/j.tetlet.2009.01.088

  日期：2009.4

  procedure for the preparation of aryl trifluoroacetamides from aryl amines is described that employs 2–4 M equiv of trifluoroacetic acid in refluxing xylene as a trifluoroacetylating agent. Addition of an amount of pyridine that is equimolar to the amount of trifluoroacetic acid present in the reaction mixture facilitates the trifluoroacetylation of rather basic arylamines.

  描述了一种从芳基胺制备芳基三氟乙酰胺的简便方法，该方法在回流的二甲苯中使用2-4 M当量的三氟乙酸作为三氟乙酰化剂。与反应混合物中存在的三氟乙酸的量等摩尔的吡啶的加入有助于碱性的芳基胺的三氟乙酰化。
• A “One-Pot” Phase Transfer Alkylation/Hydrolysis of<i>o</i>-Nitrotrifluoroacetanilides. A Convenient Route to<i>N</i>-ALKYL<i>o</i>-Phenylenediamines
  作者：Samuel A. Brown、Carmelo J. Rizzo

  DOI：10.1080/00397919608003827

  日期：1996.11

  Abstract A variety of o-nitrotrifluoroacetanilides undergo a one-pot alkylation/hydrolysis to give N-alkyl o-nitroanilines in 40–94% yield. Dimethylsulfate, benzyl bromide and 1-bromo-propane were used as the electrophiles.

  摘要 多种邻硝基三氟乙酰苯胺经过一锅烷基化/水解，以 40-94% 的产率得到 N-烷基邻硝基苯胺。硫酸二甲酯、溴化苄和 1-溴丙烷用作亲电试剂。
• Effect of cyclodextrins on the hydrolysis of amides
  作者：Alejandro Granados、Rita H. De Rossi

  DOI：10.1021/jo00059a030

  日期：1993.3

  The hydrolysis of p-nitrotrifluoroacetanilide (1), trifluoroacetanilide (2), m-nitrotrifluoroacetanilide (3), and p-nitroacetanilide (4) was studied in the presence of cyclodextrins. The reactions of 1 are catalyzed by alpha-cyclodextrin (alpha-CD) and beta-cyclodextrin (beta-CD) and also by (hydroxypropyl)cyclodextrin (HPCD). The hydrolysis of 4 is catalyzed by beta-CD. The reaction of 2 is inhibited by beta-CD and so is the reaction of 3 by HPCD. Compounds 1 and 4 form two types of inclusion complexes with beta-CD, a 1:1 and a 1:2 substrate:cyclodextrin complex. Both types of complexes react faster than the free substrate, and for 1 at pH = 7 all the catalysis is due to the reaction of the 1:2 complex since the 1:1 complex reacts at about the same rate as the free substrate. The results are explained in terms of two mechanisms: one which involves the acylation of CD by the amides and another which predominates at neutral pH where the two cyclodextrins complexing the substrate stabilize the transition state for water addition.
• US7329681B2
  申请人：——

  公开号：US7329681B2

  公开（公告）日：2008-02-12
• Inhibitors of IMPDH enzyme
  申请人：Vertex Pharmaceuticals, Incorporated

  公开号：US06344465B1

  公开（公告）日：2002-02-05

  The present invention relates to a novel class of compounds which are IMPDH inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting IMPDH enzyme activity and consequently, may be advantageously used as therapeutic agents for IMPDH mediated processes. This invention also relates to methods for inhibiting the activity of IMPDH using the compounds of this invention and related compounds.

  本发明涉及一类新型的IMPDH抑制剂化合物。该发明还涉及包含这些化合物的药物组合物。本发明的化合物和药物组合物特别适用于抑制IMPDH酶活性，因此可以优势地用作IMPDH介导的过程的治疗剂。本发明还涉及使用本发明的化合物和相关化合物抑制IMPDH活性的方法。