ethyl 3-(5-methoxy-2-nitrobenzoyl)-1-pentanoyl-Δ²-pyrazoline-5-carboxylate | 710300-31-5

• 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)-1-pentanoyl-Δ²-pyrazoline-5-carboxylate
• 英文别名: Ethyl 5-(5-methoxy-2-nitrobenzoyl)-2-pentanoyl-3,4-dihydropyrazole-3-carboxylate；ethyl 5-(5-methoxy-2-nitrobenzoyl)-2-pentanoyl-3,4-dihydropyrazole-3-carboxylate
• CAS: 710300-31-5
• 化学式: C₁₉H₂₃N₃O₇
• 分子量: 405.408
• InChiKey: NWLBPCAYTZTLQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 3-(5-methoxy-2-nitrobenzoyl)-1-pentanoyl-Δ²-pyrazoline-5-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以80%的产率得到ethyl 3-(2-amino-5-methoxybenzoyl)-1-pentanoyl-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
• 作为产物：
  描述：

  5-methoxy-2-nitrophenyl vinyl ketone 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 13.0h， 生成 ethyl 3-(5-methoxy-2-nitrobenzoyl)-1-pentanoyl-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

• 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.