ethyl 3-(5-methoxy-2-nitrobenzoyl)-Δ²-pyrazoline-5-carboxylate | 710300-07-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-(5-methoxy-2-nitrobenzoyl)-Δ²-pyrazoline-5-carboxylate
• 英文别名: ethyl 3-(5-methoxy-2-nitrobenzoyl)-4,5-dihydro-1H-pyrazole-5-carboxylate
• CAS: 710300-07-5
• 化学式: C₁₄H₁₅N₃O₆
• 分子量: 321.29
• InChiKey: GOGMVLXFWLGZEV-UHFFFAOYSA-N

物化性质

• 熔点：
  144-146 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  501.8±60.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 3-(5-methoxy-2-nitrobenzoyl)-Δ²-pyrazoline-5-carboxylate 在 palladium on activated charcoal 氢气 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0~65.0 ℃ 、482.64 kPa 条件下， 反应 10.5h， 生成 1-acetyl-3-(2-amino-5-methoxybenzoyl)-Δ²-pyrazoline-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and iNOS/nNOS inhibitory activities of new benzoylpyrazoline derivatives

  摘要：

  A series of new Delta(2)-pyrazoline derivatives has been synthesized by means of a 1,3-dipolar-cycloaddition reaction. Ethyl 3-(5-methoxy-2-nitroben zoyl)-Delta(2)-pyrazoline-5-carboxylate (5a) has been designed for the formation of the benzoylpyrazoline system present in these derivatives. Two synthetic routes have been utilized changing the starting products in the cycloaddition reaction. In both routes, the majority product obtained was only a Delta(2)-pyrazoline. The intermediate ethyl 1-acyl-3-(2-nitrobenzoyl-5 -substituted)-Delta(2)-pyrazoline-5-carboxylate derivatives have been transformed into the final compounds by means of several chemical treatments. The compounds have been biologically evaluated as inhibitors of nitric oxide synthase (NOS), showing better affinity towards the inducible NOS isoform than versus neuronal NOS. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.013
• 作为产物：
  描述：

  5-甲氧基-2-硝基苯甲酰氯 以 乙醚 为溶剂， 反应 19.0h， 生成 ethyl 3-(5-methoxy-2-nitrobenzoyl)-Δ²-pyrazoline-5-carboxylate
  参考文献：
  名称：

  Synthesis and iNOS/nNOS inhibitory activities of new benzoylpyrazoline derivatives

  摘要：

  A series of new Delta(2)-pyrazoline derivatives has been synthesized by means of a 1,3-dipolar-cycloaddition reaction. Ethyl 3-(5-methoxy-2-nitroben zoyl)-Delta(2)-pyrazoline-5-carboxylate (5a) has been designed for the formation of the benzoylpyrazoline system present in these derivatives. Two synthetic routes have been utilized changing the starting products in the cycloaddition reaction. In both routes, the majority product obtained was only a Delta(2)-pyrazoline. The intermediate ethyl 1-acyl-3-(2-nitrobenzoyl-5 -substituted)-Delta(2)-pyrazoline-5-carboxylate derivatives have been transformed into the final compounds by means of several chemical treatments. The compounds have been biologically evaluated as inhibitors of nitric oxide synthase (NOS), showing better affinity towards the inducible NOS isoform than versus neuronal NOS. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.013

文献信息

• An unexpected aromatization during the N-alkylation reaction of 3,4-dihydro-1H-pyrazole derivatives: insight into the reaction mechanism
  作者：Luisa C. López-Cara、M. Encarnación Camacho、María D. Carrión、Miguel A. Gallo、Antonio Espinosa、Antonio Entrena

  DOI：10.1016/j.tetlet.2006.06.141

  日期：2006.8

  In this letter we describe the unexpected aromatization that takes place during the N-alkylation reaction performed on several 3-(2-nitrobenzoyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid methyl esters, giving rise to a mixture of 1-alkyl-3-(2-nitrobenzoyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid methyl esters and 1-alkyl-3-(2-nitrobenzoyl)-1H-pyrazole-5-carboxylic acid methyl esters.

  在这封信中，我们描述了在几种3-（2-硝基苯甲酰基）-4,5-二氢-1 H-吡唑-5-羧酸甲酯进行的N-烷基化反应过程中发生的意外芳香化反应1-烷基-3-（2-硝基苯甲酰基）-4,5-二氢-1 H-吡唑-5-羧酸甲酯与1-烷基-3-（2-硝基苯甲酰基）-1 H-吡唑-5的混合物-羧酸甲酯。
• Pyrazoles and pyrazolines as neural and inducible nitric oxide synthase (nNOS and iNOS) potential inhibitors (III)
  作者：M. Dora Carrión、Luisa C. López Cara、M. Encarnación Camacho、Víctor Tapias、Germaine Escames、Darío Acuña-Castroviejo、Antonio Espinosa、Miguel A. Gallo、Antonio Entrena

  DOI：10.1016/j.ejmech.2008.01.014

  日期：2008.11

  We have previously described a series of 4,5-dihydro-1H-pyrazole as moderately potent nNOS inhibitors. As a follow up of these studies, we report here the preparation and the preliminary evaluation of a series of 1-alkyl-3-benzoyl-4,5-dihydro-1H-pyrazole and 1-alkyl-3-benzoyl-1H-pyrazole as potential inhibitors of both neuronal and inducible nitric oxide synthases (nNOS and iNOS). None of the reported compounds exhibited significant iNOS or nNOS inhibition, although the 1-benzyl-3-(2-amino-5-chlorobenzoyl)-1H-pyrazole-5-carboxylic acid ethyl ester derivative (101), which shows an inhibition of 50% versus iNOS at a 1 mM final concentration and no activity against nNOS, is potentially amenable of further optimization. The reasons for the inactivity of the reported series are discussed on the basis of docking studies. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Synthesis and iNOS/nNOS inhibitory activities of new benzoylpyrazoline derivatives
  作者：M.Dora Carrión、M.Encarnación Camacho、Josefa León、Germaine Escames、Vı́ctor Tapias、Darı́o Acuña-Castroviejo、Miguel A Gallo、Antonio Espinosa

  DOI：10.1016/j.tet.2004.03.013

  日期：2004.4

  A series of new Delta(2)-pyrazoline derivatives has been synthesized by means of a 1,3-dipolar-cycloaddition reaction. Ethyl 3-(5-methoxy-2-nitroben zoyl)-Delta(2)-pyrazoline-5-carboxylate (5a) has been designed for the formation of the benzoylpyrazoline system present in these derivatives. Two synthetic routes have been utilized changing the starting products in the cycloaddition reaction. In both routes, the majority product obtained was only a Delta(2)-pyrazoline. The intermediate ethyl 1-acyl-3-(2-nitrobenzoyl-5 -substituted)-Delta(2)-pyrazoline-5-carboxylate derivatives have been transformed into the final compounds by means of several chemical treatments. The compounds have been biologically evaluated as inhibitors of nitric oxide synthase (NOS), showing better affinity towards the inducible NOS isoform than versus neuronal NOS. (C) 2004 Elsevier Ltd. All rights reserved.