1-(4-chlorophenyl)-2-(1-p-tolylethylidene)hydrazine | 386272-18-0

• 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-(4-chlorophenyl)-2-(1-p-tolylethylidene)hydrazine
• CAS: 386272-18-0
• 化学式: C₁₅H₁₅ClN₂
• 分子量: 258.75
• InChiKey: RLVHUFBXHLQGHW-UHFFFAOYSA-N

物化性质

• 沸点：
  369.9±52.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  24.39
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-2-(1-p-tolylethylidene)hydrazine 在 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 15.5h， 生成 5-{[1-(4-chlorophenyl)-3-(p-tolyl)-1H-pyrazol-4-yl]methylene}-2-imino-3-[2-methyl-3-(tri-fluoromethyl)phenyl]thiazolidin-4-one
  参考文献：
  名称：

  Synthesis, antimycobacterial, cytotoxicity, anti‐inflammatory, in silico studies and molecular dynamics of pyrazole‐embedded thiazolidin‐4‐one hybrids

  摘要：

  AbstractIn the present investigation, we devolved and synthesized a new series of pyrazole‐embedded thiazolidin‐4‐one derivatives (9a–p) with the goal to produce promising antitubercular leads. The in vitro antimycobacterial activity of the synthesized compounds was tested against replicating and nonreplicating Mtb H37Rv strains. With MIC ranging from 3.03 to 22.55 µg/ml, five compounds (9a, 9c, 9d, 9e, and 9f) emerged as promising antitubercular agents. The active molecules were nontoxic to normal Vero cells. All the synthesized compounds were evaluated for in vitro anti‐inflammatory studies. Compounds 9a, 9b, 9c, 9h, and 9i exhibited excellent anti‐inflammatory efficacy. Docking study was performed to understand the binding pattern of the significantly active compound 9a with 1P44.

  DOI：

  10.1002/ardp.202200444
• 作为产物：
  描述：

  对氯苯肼盐酸盐 、 对甲基苯乙酮 在 溶剂黄146 、 sodium hydroxide 作用下， 反应 1.0h， 生成 1-(4-chlorophenyl)-2-(1-p-tolylethylidene)hydrazine
  参考文献：
  名称：

  1,3,4-Trisubstituted pyrazole bearing a 4-(chromen-2-one) thiazole: synthesis, characterization and its biological studies

  摘要：

  3-{2-[N′-(1,3-二取代-1H-吡唑-4-基-甲基)-肼基]-噻唑-4-基}-香豆素-2-酮类化合物（10a-l）被合成、表征并用于对抗各种微生物的体外抗菌研究。大多数化合物具有生物活性。

  DOI：

  10.1039/c5ra04995d

文献信息

• Synthesis of novel 1,3,4-trisubstituted pyrazoles as anti-inflammatory and analgesic agents
  作者：Fatma A. Ragab、Nagwa M. Abdel Gawad、Hanan H. Georgey、Mona F. Said

  DOI：10.1016/j.ejmech.2013.03.005

  日期：2013.5

  Some novel 1,3,4-trisubstituted pyrazoles were synthesized and screened for their anti-inflammatory and analgesic activities as well as their ulcerogenic liability. They showed anti-inflammatory and analgesic activities with better GIT tolerance than the standard drug phenylbutazone. In addition, IC50 values for 5e and 8e were recorded. Compound 5e was found to be the most active one as anti-inflammatory

  合成了一些新颖的1,3,4-三取代吡唑，并筛选了它们的抗炎和镇痛活性以及致溃疡作用。他们显示出比标准药物苯基丁a具有更好的GIT耐受性的抗炎和镇痛活性。另外，记录了5e和8e的IC 50值。发现化合物5e作为抗炎和止痛剂是最活性的。另一方面，还进行了COX-1 / COX-2同工酶的选择性，对两种同工型均表现出相同的抑制作用。
• Novel pyrazole‐clubbed thiophene derivatives via Gewald synthesis as antibacterial and anti‐inflammatory agents
  作者：Soukhyarani G. Nayak、Boja Poojary、Vinuta Kamat

  DOI：10.1002/ardp.202000103

  日期：2020.12

  Schiff bases by condensing 2‐amino‐5‐(2,4‐dichlorophenyl)thiophene‐3‐carbonitrile and 1,3‐disubstituted‐1H‐pyrazole‐4‐carbaldehydes, and to investigate their biological activity. The compounds were synthesized via Gewald synthesis and characterized by spectral data and elemental analyses. They were screened for their in vitro antibacterial and anti‐inflammatory activities. The synthesized compounds

  本研究的目的是通过缩合 2-氨基-5-(2,4-二氯苯基)噻吩-3-甲腈和 1,3-二取代-1H-吡唑-4-甲醛来合成新的有效席夫碱，并研究它们的生物活性。这些化合物是通过 Gewald 合成法合成的，并通过光谱数据和元素分析进行​​表征。筛选了它们的体外抗菌和抗炎活性。还使用微孔板 Alamar Blue 测定评估了合成的化合物对结核分枝杆菌 H37Rv 的体外抗结核活性。化合物 8b、8c、8f、8g、8k、8n 和 8o 显示出良好的抗菌活性。取代的吡唑与牛蛋白之间的相互作用显示出有希望的抗炎活性。实验结果表明化合物 8a 是一种很有前景的抗结核药物。溶血试验证实这些化合物是无毒的，溶血百分比范围为 3.6 至 20.1，浓度为 1 毫克/毫升。结果表明，吡唑环和杂环部分上的取代模式对生物活性有影响。
• Antitubercular and Antimicrobial Activity of NH4VO3 Promoted 1,4- Dihydropyridine Incorporated 1,3,4-trisubstituted Pyrazole
  作者：Nandam Harikrishna、Arun M. Isloor、K. Ananda、Tanya Parish、Joazaizulfazli Jamalis、Hazem A. Ghabbour、Hoong-Kun Fun

  DOI：10.2174/1570180813666161103145224

  日期：2017.6.6

  synthesized from substituted acetylated aryls and substituted phenylhydrazine by the multistep reaction. Method: The target compounds 1,4-dihydropyridine derivatives were obtained from green synthesis of 1,3-disubstituted phenyl-1H-pyrazole-4-carbaldehydes 4a-i with ethyl acetoacetate and methyl acetoacetate at higher temperatures in the presence of ammonium acetate and the catalytic amount of ammonium metavanadate

  背景：以取代乙酰化芳基和取代苯肼为原料，通过多步反应合成了一系列含有 1,4-二氢吡啶衍生物 5a-i 和 6a-i 的新型吡唑。方法: 目标化合物 1,4-二氢吡啶衍生物由 1,3-二取代苯基-1H-吡唑-4-甲醛 4a-i 与乙酰乙酸乙酯和乙酰乙酸甲酯在较高温度下在醋酸铵和偏钒酸铵（NH4VO3）的催化量。偏钒酸铵的作用是提高反应速率并获得高产率。结果：新合成的含有吡唑衍生物的 1,4-二氢吡啶部分的结构通过 FT-IR、NMR 和质谱研究得到证实。通过S-XRD研究证实了化合物5b的结构。更多，对这些化合物进行了体外抗结核和抗微生物研究。发现化合物 5a、5b、5i、6a、6b、6g、6h 和 6i 对所有细菌微生物都有活性。结论：上述化合物对结核分枝杆菌的最低 MIC 在 3.12-12.5 μg/ml 之间，对耻垢分枝杆菌、金黄色葡萄球菌和铜绿假单胞菌的 MIC 值在 7.8-15
• Design and synthesis of novel quinazolinone-pyrazole derivatives as potential α-glucosidase inhibitors: Structure-activity relationship, molecular modeling and kinetic study
  作者：Fateme Azimi、Homa Azizian、Mohammad Najafi、Farshid Hassanzadeh、Hojjat Sadeghi-aliabadi、Jahan B. Ghasemi、Mohammad Ali Faramarzi、Somayeh Mojtabavi、Bagher Larijani、Lotfollah Saghaei、Mohammad Mahdavi

  DOI：10.1016/j.bioorg.2021.105127

  日期：2021.9

  structure–activity relationship suggested that the variation in the inhibitory activities of the compounds affected by different substitutions on phenyl rings of diphenyl pyrazole moiety. The enzyme kinetic studies of the most potent compound 9i revealed that it inhibited α-glucosidase in a competitive mode with a Ki of 56 μM. Molecular docking study was performed to predict the putative binding interaction. As expected

  在这项研究中，设计、合成了一系列新的喹唑啉酮-吡唑杂化物，并筛选了它们的 α-葡萄糖苷酶抑制活性。的结果在体外筛选表明所有分子杂交显示出更多的抑制活性（IC 50值从60.5±0.3μM-186.6±20μM范围）相比于标准阿卡波糖（IC 50 = 750.0 ± 10.0 µM）。有限的构效关系表明化合物抑制活性的变化受二苯基吡唑部分苯环上不同取代的影响。最有效的化合物 9i 的酶动力学研究表明，它以竞争模式抑制 α-葡萄糖苷酶，Ki 为 56 μM。进行分子对接研究以预测假定的结合相互作用。正如预期的那样，初始结构设计中使用的所有药效基团在与酶结合位点的相互作用中都发挥着关键作用。此外，通过进行分子动力学研究和 MM-GBSA 计算，
• Synthesis of 3-(1, 3-Diphenyl-1<i>H</i>-pyrazol-4-yl) Propanoic Acids Using Diimide Reduction
  作者：M. Deepa、V. Harinadha Babu、R. Parameshwar、B. Madhava Reddy

  DOI：10.1155/2012/481682

  日期：——

  Pyrazole-1H-4-yl-acrylic acids (3a-j) were prepared from pyrazole-1H-4-carbaldehydes which in turn were prepared by the Vilsmeier-Haack reaction of phenyl hydrazone derivatives (1a-j). The reaction of pyrazole-1H-4-yl-acrylic acids to 3-(1, 3-diphenyl-1H-pyrazol-4-yl) propanoic acids (4a-j) was carried out using Pd-charcoal and diimide methods and % yields were compared. Though the yields may be slightly less in diimide method, the method was found to be economical, highly effective with simple operating procedure.

  从苯基腙衍生物（1a-j）的Vilsmeier-Haack反应制备的吡唑-1H-4-基丙烯酸（3a-j）制备而成的吡唑-1H-4-基丙烯酸（3a-j）制备自吡唑-1H-4-羰基醛。使用Pd-木炭和二亚甲基方法进行吡唑-1H-4-基丙烯酸反应制备3-(1,3-二苯基-1H-吡唑-4-基)丙酸（4a-j），并比较产率。尽管二亚甲基方法的产率可能略低，但该方法被证明在操作程序简单的情况下经济高效。