1-ethyl-3-(2-nitrobenzoyl)-1H-pyrazole-5-carboxylic acid ethyl ester | 910537-66-5

• 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: 1-ethyl-3-(2-nitrobenzoyl)-1H-pyrazole-5-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-ethyl-5-(2-nitrobenzoyl)pyrazole-3-carboxylate；ethyl 2-ethyl-5-(2-nitrobenzoyl)pyrazole-3-carboxylate
• CAS: 910537-66-5
• 化学式: C₁₅H₁₅N₃O₅
• 分子量: 317.301
• InChiKey: CEENSRNHMRHBKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-ethyl-3-(2-nitrobenzoyl)-1H-pyrazole-5-carboxylic acid ethyl ester 在 铁粉 、 iron(II) sulfate 作用下， 以 水 为溶剂， 反应 3.0h， 以70%的产率得到Ethyl 5-(2-aminobenzoyl)-2-ethylpyrazole-3-carboxylate
  参考文献：
  名称：

  Pyrazoles and pyrazolines as neural and inducible nitric oxide synthase (nNOS and iNOS) potential inhibitors (III)

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2008.01.014
• 作为产物：
  描述：

  硫酸二乙酯 、 ethyl 3-(2-nitrobenzoyl)-Δ²-pyrazoline-5-carboxylate 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以46%的产率得到1-ethyl-3-(2-nitrobenzoyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  3,4-二氢-1 H-吡唑衍生物的N-烷基化反应过程中出乎意料的芳香化：了解反应机理

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2006.06.141

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.