1-(4,5-dimethoxy-2-nitrophenyl)prop-2-en-1-one | 1445859-30-2

• 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: 1-(4,5-dimethoxy-2-nitrophenyl)prop-2-en-1-one
• 英文别名: 1-(4,5-Dimethoxy-2-nitrophenyl)prop-2-en-1-one
• CAS: 1445859-30-2
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: BCPPLEWEXACGIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4,5-dimethoxy-2-nitrophenyl)prop-2-en-1-one 在 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 3-(4,5-dimethoxy-2-nitrophenyl)-1-phenylpropanoyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group

  摘要：

  In a preliminary article, we reported a series of 4,5-dihydro-1H-pyrazole derivatives as neuronal nitric oxide synthase (nNOS) inhibitors. Here we present the data about the inhibition of inducible nitric oxide synthase (iNOS) of these compounds. In general, we can confirm that these pyrazoles are nNOS selective inhibitors. In addition, taking these compounds as a reference, we have designed and synthesized a series of new derivatives by modification of the heterocycle in 1-position, and by introduction of electrondonating or electron-withdrawing substituents in the aromatic ring. These derivatives have been evaluated as nNOS and iNOS inhibitors in order to identify new compounds with improved activity and selectivity. Compound 3r, with three methoxy electron-donating groups in the phenyl moiety, is the most potent nNOS inhibitor, showing good selectivity nNOS/iNOS. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.016
• 作为产物：
  描述：

  6-硝基藜芦醛 在 chromium(VI) oxide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.67h， 生成 1-(4,5-dimethoxy-2-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  基于噻二唑啉和吡唑啉的甲酰胺和硫代酰胺：合成和抑制一氧化氮合酶

  摘要：

  已经开发了两个新的吡唑啉和噻二唑啉杂环家族。报道了它们对一氧化氮合酶的两种不同异构体（诱导型和神经元 NOS）的抑制活性。新的衍生物合成结合芳基噻二唑啉或芳基吡唑啉骨架和甲酰胺或硫代甲酰胺部分，分别用作起始原料 2-硝基苯甲酸乙酯或取代的硝基苯甲醛。最终分子的构效关系根据芳环中的 R1 自由基效应、杂环系统中的 Y 原子、主链中的 X 杂原子以及甲酰胺或硫代硫酰胺中的 R2 取代基进行讨论。一般来说，噻二唑啉 (5a-e) 优先抑制神经元同种型；其中，5a 是最好的 nNOS 抑制剂（1 mM 时为 74.11%，IC50 = 420 μM）。相比之下，吡唑啉 (6a-r) 作为 iNOS 的表现优于 nNOS 抑制剂，6m 是该系列中最好的分子（1 mM iNOS 抑制时为 76.86%，IC50 = 130 μM）并且是所有测试化合物中最有效的。

  DOI：

  10.1155/2018/9242616

文献信息

• Organocatalytic β-Azidation of Enones Initiated by an Electron-Donor–Acceptor Complex
  作者：Rajendra P. Shirke、S. S. V. Ramasastry

  DOI：10.1021/acs.orglett.7b02861

  日期：2017.10.6

  β-unsaturated ketones is described. Reaction of the Zhdankin azidoiodane with enones in the presence of a catalytic amount of an amine provides β-azido ketones via the formation of an electron-donor–acceptor complex. The application of this protocol is demonstrated through one-step elaborations leading to the synthesis of unprecedented classes of 1,2,3-triazoles.

  描述了一种操作简单的α，β-不饱和酮的有机催化β-叠氮化。Zhdankin叠氮碘烷与烯酮在催化量的胺存在下的反应通过电子给体-受体配合物的形成提供了β-叠氮基酮。该协议的应用通过一步一步精炼来证明，该合成导致合成前所未有的1,2,3-三唑类。
• Thiadiazoline- and Pyrazoline-Based Carboxamides and Carbothioamides: Synthesis and Inhibition against Nitric Oxide Synthase
  作者：Fabio Arias、M. Encarnación Camacho、M. Dora Carrión、Meriem Chayah、Miguel Romero、Juan Duarte、Miguel A. Gallo

  DOI：10.1155/2018/9242616

  日期：——

  novel derivatives were synthesized combining the arylthiadiazoline or arylpyrazoline skeleton and a carboxamide or carbothioamide moiety, used as starting material ethyl 2-nitrobenzoates or substituted nitrobenzaldehydes, respectively. The structure-activity relationships of final molecules are discussed in terms of the R1 radical effects in the aromatic ring, the Y atom in the heterocyclic system, the

  已经开发了两个新的吡唑啉和噻二唑啉杂环家族。报道了它们对一氧化氮合酶的两种不同异构体（诱导型和神经元 NOS）的抑制活性。新的衍生物合成结合芳基噻二唑啉或芳基吡唑啉骨架和甲酰胺或硫代甲酰胺部分，分别用作起始原料 2-硝基苯甲酸乙酯或取代的硝基苯甲醛。最终分子的构效关系根据芳环中的 R1 自由基效应、杂环系统中的 Y 原子、主链中的 X 杂原子以及甲酰胺或硫代硫酰胺中的 R2 取代基进行讨论。一般来说，噻二唑啉 (5a-e) 优先抑制神经元同种型；其中，5a 是最好的 nNOS 抑制剂（1 mM 时为 74.11%，IC50 = 420 μM）。相比之下，吡唑啉 (6a-r) 作为 iNOS 的表现优于 nNOS 抑制剂，6m 是该系列中最好的分子（1 mM iNOS 抑制时为 76.86%，IC50 = 130 μM）并且是所有测试化合物中最有效的。
• Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group
  作者：M. Dora Carrión、Mariem Chayah、Antonio Entrena、Ana López、Miguel A. Gallo、Darío Acuña-Castroviejo、M. Encarnación Camacho

  DOI：10.1016/j.bmc.2013.05.016

  日期：2013.7

  In a preliminary article, we reported a series of 4,5-dihydro-1H-pyrazole derivatives as neuronal nitric oxide synthase (nNOS) inhibitors. Here we present the data about the inhibition of inducible nitric oxide synthase (iNOS) of these compounds. In general, we can confirm that these pyrazoles are nNOS selective inhibitors. In addition, taking these compounds as a reference, we have designed and synthesized a series of new derivatives by modification of the heterocycle in 1-position, and by introduction of electrondonating or electron-withdrawing substituents in the aromatic ring. These derivatives have been evaluated as nNOS and iNOS inhibitors in order to identify new compounds with improved activity and selectivity. Compound 3r, with three methoxy electron-donating groups in the phenyl moiety, is the most potent nNOS inhibitor, showing good selectivity nNOS/iNOS. (C) 2013 Elsevier Ltd. All rights reserved.