5-(4-Chlorophenyl)-2-phenylpyrazole-3-carbaldehyde | 1002101-96-3

• 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)-2-phenylpyrazole-3-carbaldehyde
• CAS: 1002101-96-3
• 化学式: C₁₆H₁₁ClN₂O
• 分子量: 282.729
• InChiKey: VJXUFEQIBSXMQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  磺胺 、 5-(4-Chlorophenyl)-2-phenylpyrazole-3-carbaldehyde 在 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 以69 %的产率得到(E)-4-(((3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-yl)methylene)amino)benzenesulfonamide
  参考文献：
  名称：

  Synthesis, Characterization and In Silico Studies of Novel (E)-4-(((3-(substituted phenyl)-1-phenyl-1H-pyrazol-5-yl)methylene)amino)benzenesulfonamide as Diuretic Agents

  摘要：

  This research delves into the examination of benzene sulphonamide derivatives featuring pyrazole rings as potential diuretics. Concentrating on their role as human carbonic anhydrase inhibitors (hCA), the investigation aims to unveil a groundbreaking diuretic drug. Six innovative benzenesulfonamide derivatives are synthesized utilizing a conventional heating process. Subsequently, employing AutoDock Vina 1.2.3, these compounds undergo molecular docking assessments and pharmacokinetic predictions at the active sites of hCA I and hCA II, while the SwissADME program is employed for pharmacokinetic forecasting. Notably, Compounds 17 and 19 exhibit robust binding affinities with hCA I and II, respectively, as evidenced by the docking study. ADME studies reveal favorable bioavailability and adherence to PAINS alerts, as well as Lipinski's rule of five requirements. Consequently, based on the findings, these compounds exhibit significant potential as diuretics in comparison to well-established acetazolamide medications.

  DOI：

  10.13005/ojc/400212
• 作为产物：
  描述：

  对氯苯乙酮 在 溶剂黄146 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 5-(4-Chlorophenyl)-2-phenylpyrazole-3-carbaldehyde
  参考文献：
  名称：

  Synthesis, Characterization and In Silico Studies of Novel (E)-4-(((3-(substituted phenyl)-1-phenyl-1H-pyrazol-5-yl)methylene)amino)benzenesulfonamide as Diuretic Agents

  摘要：

  This research delves into the examination of benzene sulphonamide derivatives featuring pyrazole rings as potential diuretics. Concentrating on their role as human carbonic anhydrase inhibitors (hCA), the investigation aims to unveil a groundbreaking diuretic drug. Six innovative benzenesulfonamide derivatives are synthesized utilizing a conventional heating process. Subsequently, employing AutoDock Vina 1.2.3, these compounds undergo molecular docking assessments and pharmacokinetic predictions at the active sites of hCA I and hCA II, while the SwissADME program is employed for pharmacokinetic forecasting. Notably, Compounds 17 and 19 exhibit robust binding affinities with hCA I and II, respectively, as evidenced by the docking study. ADME studies reveal favorable bioavailability and adherence to PAINS alerts, as well as Lipinski's rule of five requirements. Consequently, based on the findings, these compounds exhibit significant potential as diuretics in comparison to well-established acetazolamide medications.

  DOI：

  10.13005/ojc/400212

文献信息

• La(OTf)₃-catalysed one-pot synthesis of pyrazole tethered imidazo[1,2-<i>a</i>]azine derivatives and evaluation of their light emitting properties
  作者：Shubham Sharma、Avijit Kumar Paul、Virender Singh

  DOI：10.1039/c9nj05426j

  日期：——

  A facile and efficient protocol has been unfolded towards the diversity-oriented synthesis of highly fluorescent pyrazole C-3(5) tethered imidazo[1,2-a]azines via an La(OTf)3 catalysed one-pot multicomponent assembly of pyrazole carbaldehydes, 2-aminoazines and isonitriles. This present protocol offers several advantages such as multiple bond formation in a single step, low catalyst loading, short

  通过La（OTf）3催化的吡唑甲醛单组分多组分组装，已实现了简便高效的方案，用于多样性导向的高荧光吡唑C-3（5）束缚的咪唑并[1,2- a ]嗪的合成。，2-氨基嗪和异腈。本方案具有几个优点，例如在一个步骤中形成多个键，催化剂用量低，反应时间短，可观的原子经济性，良好的官能团耐受性，可扩展性和易于执行的反应条件。吡唑基咪唑并[1,2的光学性质一个]吖嗪进行了研究，并且它们表现出优异的荧光量子产率（Φ ˚F高达83％）。
• An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides
  作者：Shubham Sharma、Dharmender Singh、Sunit Kumar、Vaishali、Rahul Jamra、Naveen Banyal、Deepika、Chandi C Malakar、Virender Singh

  DOI：10.3762/bjoc.19.22

  日期：——

  described for the synthesis of pyrazole-tethered thioamide and amide conjugates. The thioamides were generated by employing a three-component reaction of diverse pyrazole C-3/4/5 carbaldehydes, secondary amines, and elemental sulfur in a single synthetic operation. The advantages of this developed protocol refer to the broad substrate scope, metal-free and easy to perform reaction conditions. Moreover

  描述了一种操作简单且无金属的方法，用于合成吡唑系硫代酰胺和酰胺缀合物。硫代酰胺是通过在单一合成操作中采用多种吡唑 C-3/4/5 甲醛、仲胺和元素硫的三组分反应生成的。该开发协议的优点是底物范围广、无金属且易于执行反应条件。此外，还使用过氧化氢作为氧化剂，通过吡唑甲醛和 2-氨基吡啶的氧化胺化合成了吡唑 C-3/5 连接的酰胺缀合物。
• Development of novel pyrazolone derivatives as inhibitors of aldose reductase: An eco-friendly one-pot synthesis, experimental screening and in silico analysis
  作者：Aparna Kadam、Bhaskar Dawane、Manisha Pawar、Harshala Shegokar、Kapil Patil、Rohan Meshram、Rajesh Gacche

  DOI：10.1016/j.bioorg.2014.02.002

  日期：2014.4

  Aldose reductase is the key enzyme of polypol pathway leading to accumulation of sorbitol. Sorbitol does not diffuse across the cell membranes easily and therefore accumulates within the cell, causing osmotic damage which leads to retinopathy (cataractogenesis), neuropathy and other diabetic complications. Currently, aldose reductase inhibitors like epalrestat, ranirestat and fidarestat are used for the amelioration of diabetic complications. However, such drugs are effective in patients having good glycemic control and less severe diabetic complications. In present study we have designed novel pyrazolone derivative and performed eco-friendly synthesis approach and tested the synthesized compounds as potential inhibitors of aldose reductase activity. Additional in silico analysis in current study indicates presence of highly conserved chemical environment in active site of goat lens aldose reductase. The reported data is expected to be useful for developing novel pyrazolone derivatives as lead compounds in the management of diabetic complications. (C) 2014 Elsevier Inc. All rights reserved.