N-(2-nitrophenyl)butyramide | 339307-16-3

• 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-nitrophenyl)butyramide
• 英文别名: 2-nitrobutyranilide；butyric acid-(2-nitro-anilide)；Buttersaeure-(2-nitro-anilid)；N-(2-nitrophenyl)butanamide
• CAS: 339307-16-3
• 化学式: C₁₀H₁₂N₂O₃
• mdl: MFCD00448089
• 分子量: 208.217
• InChiKey: QGQDJJOVVKDXOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  50-51 °C
• 沸点：
  400.3±28.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-nitrophenyl)butyramide 在 human butyrylcholinesterase EC 3.1.1.8 、 Tris buffer 作用下， 以 水 、 乙腈 为溶剂， 生成 2-硝基苯胺
  参考文献：
  名称：

  On the active site for hydrolysis of aryl amides and choline esters by human cholinesterases

  摘要：

  Cholinesterases, in addition to their well-known esterase action, also show an aryl acylamidase (AAA) activity whereby they catalyze the hydrolysis of amides of certain aromatic amines. The biological function of this catalysis is not known. Furthermore, it is not known whether the esterase catalytic site is involved in the AAA activity of cholinesterases. It has been speculated that the AAA activity, especially that of butyrylcholinesterase (BuChE), may be important in the development of the nervous system and in pathological processes such as formation of neuritic plaques in Alzheimer's disease (AD). The substrate generally used to study the AAA activity of cholinesterases is N-(2-nitrophenyl)acetamide. However, use of this substrate requires high concentrations of enzyme and substrate, and prolonged periods of incubation at elevated temperature. As a consequence, difficulties in performing kinetic analysis of AAA activity associated with cholinesterases have hampered understanding this activity. Because of its potential biological importance, we sought to develop a more efficient and specific substrate for use in studying the AAA activity associated with BuChE, and for exploring the catalytic site for this hydrolysis. Here, we describe the structure-activity relationships for hydrolysis of anilides by cholinesterases. These studies led to a substrate, N-(2-nitrophenyl)trifluoroacetamide, that was hydrolyzed several orders of magnitude faster than N-(2-nitrophenyl)acetamide by cholinesterases. Also, larger N-(2-nitrophenyl)alkylamides were found to be more rapidly hydrolyzed by BuChE than N-(2-nitrophenyl)acetamide and, in addition, were more specific for hydrolysis by BuChE. Thus, N-(2-nitrophenyl)alkylamides with six to eight carbon atoms in the acyl group represent suitable specific substrates to investigate further the function of the AAA activity of BuChE. Based on the substrate structure-activity relationships and kinetic studies, the hydrolysis of anilides and esters of choline appears to utilize the same catalytic site in BuChE. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.021
• 作为产物：
  描述：

  2-硝基乙酰苯胺 在 human butyrylcholinesterase EC 3.1.1.8 、 Tris buffer 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 N-(2-nitrophenyl)butyramide
  参考文献：
  名称：

  On the active site for hydrolysis of aryl amides and choline esters by human cholinesterases

  摘要：

  Cholinesterases, in addition to their well-known esterase action, also show an aryl acylamidase (AAA) activity whereby they catalyze the hydrolysis of amides of certain aromatic amines. The biological function of this catalysis is not known. Furthermore, it is not known whether the esterase catalytic site is involved in the AAA activity of cholinesterases. It has been speculated that the AAA activity, especially that of butyrylcholinesterase (BuChE), may be important in the development of the nervous system and in pathological processes such as formation of neuritic plaques in Alzheimer's disease (AD). The substrate generally used to study the AAA activity of cholinesterases is N-(2-nitrophenyl)acetamide. However, use of this substrate requires high concentrations of enzyme and substrate, and prolonged periods of incubation at elevated temperature. As a consequence, difficulties in performing kinetic analysis of AAA activity associated with cholinesterases have hampered understanding this activity. Because of its potential biological importance, we sought to develop a more efficient and specific substrate for use in studying the AAA activity associated with BuChE, and for exploring the catalytic site for this hydrolysis. Here, we describe the structure-activity relationships for hydrolysis of anilides by cholinesterases. These studies led to a substrate, N-(2-nitrophenyl)trifluoroacetamide, that was hydrolyzed several orders of magnitude faster than N-(2-nitrophenyl)acetamide by cholinesterases. Also, larger N-(2-nitrophenyl)alkylamides were found to be more rapidly hydrolyzed by BuChE than N-(2-nitrophenyl)acetamide and, in addition, were more specific for hydrolysis by BuChE. Thus, N-(2-nitrophenyl)alkylamides with six to eight carbon atoms in the acyl group represent suitable specific substrates to investigate further the function of the AAA activity of BuChE. Based on the substrate structure-activity relationships and kinetic studies, the hydrolysis of anilides and esters of choline appears to utilize the same catalytic site in BuChE. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.021

文献信息

• A short synthesis of phenanthro[2,3- d ]imidazoles from dehydroabietic acid. Application of the methodology as a convenient route to benzimidazoles
  作者：Tatiana Fonseca、Bárbara Gigante、Thomas L Gilchrist

  DOI：10.1016/s0040-4020(00)01158-3

  日期：2001.2

  Methyl cis-deisopropyldehydroabietate was selectively nitrated at the 12-position by reaction with ‘claycop’, a montmorillonite clay impregnated with copper(II) nitrate. The 12-nitro compound was reduced to the corresponding amine and this was subjected to a combined acylation and ortho nitration. The compounds so produced were further converted into octahydro-1H-phenanthro[2,3-d]imidazoles by reductive

  通过与“ claycop”（一种浸有硝酸铜（II）的蒙脱土）反应，在12位选择性地将顺式-异异丙基脱氢松香酸甲酯硝化。将12-硝基化合物还原为相应的胺，并将其进行酰化和邻硝化的组合。通过还原环化将如此产生的化合物进一步转化为八氢-1 H-菲并[2,3- d ]咪唑。结果表明，相同的酰化-邻硝化方法可从苯胺短时间合成2-取代的苯并咪唑。
• Facile synthesis of thiazoles via an intramolecular thia-Michael strategy
  作者：Pradip K. Sasmal、S. Sridhar、Javed Iqbal

  DOI：10.1016/j.tetlet.2006.09.157

  日期：2006.12

  A mild and efficient method for the synthesis of substituted thiazoles is reported via one-pot N-desilylation, thioacylation/oxythioacylation/thiothioacylation followed by thia-Michael cycloisomerisation. This method has a general applicability to introduce various oxo and thio functionalities including aliphatic and aromatic moieties, especially at the C2-position of thiazoles.

  据报道，一种温和有效的合成取代噻唑的方法是通过一锅N-去甲硅烷基化，硫代酰化/氧硫代酰化/硫代硫酰化，然后进行噻-迈克尔环异构化。该方法通常适用于引入各种氧代和硫代官能团，包括脂族和芳族部分，尤其是在噻唑的C 2位。
• 2-Substituted Aniline as a Simple Scaffold for LuxR-Regulated QS Modulation
  作者：Sizhe Li、Julien Wawrzyniak、Yves Queneau、Laurent Soulère

  DOI：10.3390/molecules22122090

  日期：——

  that the 2-substituted aniline motif fits within the LuxR binding site at the place of the lactone moiety of AHL, and the biological evaluation revealed QS antagonisitic activity for several compounds, validating the hypothesis that this scaffold acts on QS. Structure activity relationships are discussed regarding interactions with the key residues of the LuxR binding site, showing significant variations

  通过对接实验和对一系列 15 种特殊合成化合物的生物学评估，研究了 2-取代苯胺基序作为设计潜在 LuxR 调节的群体感应 (QS) 调节剂的支架的能力。考虑了苯胺、2-乙酰苯胺和 2-硝基苯胺，以及它们的 N-酰化衍生物。对接实验表明，2-取代的苯胺基序适合 AHL 内酯部分位置的 LuxR 结合位点，生物学评估揭示了几种化合物的 QS 拮抗活性，验证了该支架作用于 QS 的假设。讨论了与 LuxR 结合位点的关键残基的相互作用的结构活性关系，显示出 H 键合模式的显着变化。
• Pyridinyl-substituted-benz imidazole derivatives and preparation
  申请人：STERLING DRUG INC.

  公开号：EP0056260A1

  公开（公告）日：1982-07-21

  2-R-5-(Py-Y)-lH-benzimidazole or pharmaceutically-acceptable acid-addition salt thereof, useful as a cardiotonic, is prepared by reacting 4-(Py-Y)-1,2-benzenediamine with a tri-(lower-alkyl)ortho-(lower-alkanoate) of the formula R-C(ORI)3, where R is hydrogen or lower-alkyl, Y is a direct linkage or lower-alkylene having one or two carbon atoms, and Py is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or with dimethylformamide dimethyl acetal or dimethylacetamide dimethyl acetal to produce said 2-R-5-(Py-Y)-1H-benzimidazole where R is methyl or ethyl respectively. The same compound where R is lower-alkyl is prepared in two steps by first reacting 4-(Py-Y)-1,2-benzenediamine with an alkanoylating agent providing alkanoyl of the formula R'-C=O to produce N2[R'C(=O)]-4-(Py-Y)-1,2-benzenediamine and heating the latter compound to produce said 2-R'-5-(Py-Y)-1H-benzimidazole, where R' is lower-alkyl. Also shown is 1-hydroxy-2-R-6-(Py-Y)-1H-benzimidazole or pharmaceutically-acceptable acid-addition salt thereof, useful as a cardiotonic and prepared by reacting 3-nitro-N-(RCO)-4-(Py-Y)-benzeneamine with hydrogen under catalytic hydrogen conditions.

  可用作强心剂的 2-R-5-(Py-Y)-lH-苯并咪唑或其药学上可接受的酸加成盐，是通过 4-(Py-Y)-1,2-苯二胺与式 R-C(ORI)3（其中 R 为氢或低级烷基）的三(低级烷基)原(低级烷酸)酯反应制备的、Y 是具有一个或两个碳原子的直链烷基或低级烷基，Py 是 4-或 3-吡啶基或具有一个或两个低级烷基取代基的 4-或 3-吡啶基，或与二甲基甲酰胺二甲基缩醛或二甲基乙酰胺二甲基缩醛生成所述 2-R-5-(Py-Y)-1H-苯并咪唑，其中 R 分别为甲基或乙基。R 为低级烷基的相同化合物分两步制备，首先将 4-(Py-Y)-1,2-苯二胺与提供式 R'-C=O 烷酰基的烷酰化剂反应，生成 N2[R'C(=O)]-4-(Py-Y)-1,2-苯二胺，然后加热后一种化合物，生成所述 2-R'-5-(Py-Y)-1H-苯并咪唑，其中 R' 为低级烷基。图中还显示了 1-羟基-2-R-6-(Py-Y)-1H-苯并咪唑或其药学上可接受的酸加成盐，可用作强心剂，其制备方法是在催化氢条件下使 3-硝基-N-(RCO)-4-(Py-Y)-苯胺与氢反应。
• LIPASE VARIANTS AND POLYNUCLEOTIDES ENCODING SAME
  申请人：Novozymes A/S

  公开号：EP2732033A1

  公开（公告）日：2014-05-21