5-(4-chlorophenyl)-3-phenyl-4,5-dihydropyrazole-1-carbaldehyde | 336168-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-3-phenyl-4,5-dihydropyrazole-1-carbaldehyde
• 英文别名: N-formyl-5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-2-pyrazoline；N-formyl-5-(4’-chlorophenyl)-3-phenyl-2-pyrazoline；5-(4-Chloro-phenyl)-3-phenyl-4,5-dihydro-pyrazole-1-carbaldehyde；3-(4-chlorophenyl)-5-phenyl-3,4-dihydropyrazole-2-carbaldehyde
• CAS: 336168-27-5
• 化学式: C₁₆H₁₃ClN₂O
• 分子量: 284.745
• InChiKey: ASSLHYVMEAHWEM-UHFFFAOYSA-N

物化性质

• 沸点：
  430.0±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)
• 溶解度：
  14.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-3-phenyl-4,5-dihydropyrazole-1-carbaldehyde 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以90%的产率得到6-chloro-2-phenyl-3,3a-dihydropyrazolo[5,1-a]isoindol-8-one
  参考文献：
  名称：

  2-(取代苯基)-3,3a-二氢-8H-吡唑并[5,1-a]异吲哚-8-酮通过查尔酮基N-甲酰基-吡唑啉的替代合成路线

  摘要：

  摘要 描述了通过基于查尔酮的 N-甲酰基-吡唑啉生成 2-(取代苯基)-3,3a-二氢-8H-吡唑并[5,1a] 异吲哚-8-酮的替代方法。通过查耳酮与水合肼在甲酸存在下的反应，在三氟乙酸（TFA）作为催化剂的存在下进行分子内弗瑞德-克来福特酰化反应，以优异的收率（81-96%）制备了 N-甲酰基-吡唑啉在乙腈中回流，以良好至极好的收率（74-94%）提供官能化的 2-（取代苯基）-3,3a-二氢-8H-吡唑并[5,1-a]异吲哚-8-酮。我们的合成路线避免了昂贵的试剂并显着提高了产量。图形概要

  DOI：

  10.1080/00397911.2011.606414
• 作为产物：
  描述：

  4-氯查耳酮 、 甲酸 在 一水合肼 作用下， 以95%的产率得到5-(4-chlorophenyl)-3-phenyl-4,5-dihydropyrazole-1-carbaldehyde
  参考文献：
  名称：

  2-(取代苯基)-3,3a-二氢-8H-吡唑并[5,1-a]异吲哚-8-酮通过查尔酮基N-甲酰基-吡唑啉的替代合成路线

  摘要：

  摘要 描述了通过基于查尔酮的 N-甲酰基-吡唑啉生成 2-(取代苯基)-3,3a-二氢-8H-吡唑并[5,1a] 异吲哚-8-酮的替代方法。通过查耳酮与水合肼在甲酸存在下的反应，在三氟乙酸（TFA）作为催化剂的存在下进行分子内弗瑞德-克来福特酰化反应，以优异的收率（81-96%）制备了 N-甲酰基-吡唑啉在乙腈中回流，以良好至极好的收率（74-94%）提供官能化的 2-（取代苯基）-3,3a-二氢-8H-吡唑并[5,1-a]异吲哚-8-酮。我们的合成路线避免了昂贵的试剂并显着提高了产量。图形概要

  DOI：

  10.1080/00397911.2011.606414

文献信息

• Synthesis, antiamoebic activity and thermal study of copper complexes of 1-formyl-2-pyrazolines
  作者：Pramod Singh、Jagmohan S. Negi、M. S. M. Rawat、Geeta Joshi nee Pant

  DOI：10.1007/s10973-011-2168-3

  日期：2013.1

  Copper complexes of 1-formyl-2-pyrazolines were prepared by the reaction of 1-formyl-2-pyrazolines with copper chloride and nitrate with methanol. The structures of copper complexes 1a–3a have been established by elemental analysis, FT-IR, UV and thermogravimetric analysis. These compounds were tested against HM1:IMSS strain of Entamoeba histolytica by the microdilution method. Complexes 2a and 3a are more active than other complexes.

  通过 1-甲酰基-2-吡唑与氯化铜和硝酸铜与甲醇的反应，制备了 1-甲酰基-2-吡唑的铜络合物。通过元素分析、傅立叶变换红外光谱、紫外光谱和热重分析，确定了铜络合物 1a-3a 的结构。采用微稀释法对这些化合物进行了抗 HM1:IMSS 型组织溶解恩塔米巴虫菌株的测试。络合物 2a 和 3a 的活性高于其他络合物。
• N-formylpyrazolines and N-benzoylpyrazolines as novel inhibitors of mammalian cathepsin B and cathepsin H
  作者：N. Raghav、S. Garg

  DOI：10.1016/j.bioorg.2014.07.012

  日期：2014.12

  Cathepsins, intracellular proteases, are known to be involved in a number of physiological processes ranging from degradation of extracellular proteins, prohormone processing, progressions of atherosclerosis, etc. High levels of cathepsins have been indicated in various pathological conditions like arthritis, cancer and other tissue degenerative disorders. One of the reasons attributed to these high levels is decrease in inhibitor concentration. Therefore, the work on the identification of small molecular weight compounds as inhibitors of cysteine proteases is of great therapeutic significance. Exploring this work in the same direction, we here present the synthesis of substituted N-formylpyrazolines and N-benzoylpyrazolines and study these as inhibitors to cysteine proteases. After a preliminary screening of the compounds as inhibitors to cysteine proteases in general, studies were carried out to study their inhibitory effects on cathepsin B and cathepsin H. SAR studies show that N-formylpyrazolines were better inhibitors than N-benzoylpyrazolines. The most potent inhibitors among the two series were nitro substituted compounds 1i and 2i with K-i values of similar to 1.1 x 10 (9) M and 19.5 x 10 (8) M for cathepsin B and K-i values of similar to 5.19 x 10 (8) M and 9.8 x 10 (7) M for cathepsin H, respectively. Docking experiments showing interaction between N-formylpyrazolines and N-benzoylpyrazolines with enzyme active sites structures also provided useful insights. (C) 2014 Elsevier Inc. All rights reserved.
• Alternate Synthesis Route of 2-(Substituted Phenyl)-3,3a-dihydro-8H-pyrazolo[5,1-<i>a</i>]isoindol-8-ones via Chalcone-Based N-Formyl-pyrazolines
  作者：Naseem Ahmed、Dharm Dev

  DOI：10.1080/00397911.2011.606414

  日期：2013.1.1

  Abstract An alternate approach to 2-(substituted phenyl)-3,3a-dihydro-8H-pyrazolo[5,l-a] isoindol-8-ones via chalcone-based N-formyl-pyrazolines is described. N-Formyl-pyrazolines were prepared in excellent yield (81–96%) by the reaction of chalcones with hydrazine hydrate in the presence of formic acid, which undergoes intramolecular Friedel–Crafts acylation in the presence of trifluoroacetic acid

  摘要 描述了通过基于查尔酮的 N-甲酰基-吡唑啉生成 2-(取代苯基)-3,3a-二氢-8H-吡唑并[5,1a] 异吲哚-8-酮的替代方法。通过查耳酮与水合肼在甲酸存在下的反应，在三氟乙酸（TFA）作为催化剂的存在下进行分子内弗瑞德-克来福特酰化反应，以优异的收率（81-96%）制备了 N-甲酰基-吡唑啉在乙腈中回流，以良好至极好的收率（74-94%）提供官能化的 2-（取代苯基）-3,3a-二氢-8H-吡唑并[5,1-a]异吲哚-8-酮。我们的合成路线避免了昂贵的试剂并显着提高了产量。图形概要