2-[2-(4-chlorobenzylidene)hydrazinyl]-4-phenyl-1,3-thiazole | 21938-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[2-(4-chlorobenzylidene)hydrazinyl]-4-phenyl-1,3-thiazole
• 英文别名: 2-(2-(4-chlorobenzylidene)hydrazinyl)-4-phenylthiazole；2-(4-chlorobenzyliden)hydrazo-4-phenylthiazole；N-[(4-chlorophenyl)methylideneamino]-4-phenyl-1,3-thiazol-2-amine
• CAS: 21938-35-2
• 化学式: C₁₆H₁₂ClN₃S
• mdl: MFCD00519096
• 分子量: 313.81
• InChiKey: YQKYELGBAMTOTP-UHFFFAOYSA-N

物化性质

• 熔点：
  246-248 °C(Solv: ethanol (64-17-5))
• 沸点：
  486.4±47.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 2-[2-(4-chlorobenzylidene)hydrazinyl]-4-phenyl-1,3-thiazole
  参考文献：
  名称：

  噻唑腙衍生物的抗氧化和抗酪氨酸酶活性的合成、评价及其在鲜切马铃薯防褐变中的应用

  摘要：

  酪氨酸酶是黑色素生物合成中的关键酶，黑色素是导致食物褐变和许多皮肤病的原因。为了开发具有双重抗氧化和抗酪氨酸酶能力的新型抗褐变剂，合成了一系列30种噻唑腙衍生物。在制备的分子中，发现6和30是最有效的酪氨酸酶抑制剂，其 IC 50值与曲酸相当。有趣的是，6在制备的分子中也具有最高的自由基清除活性。抑制动力学研究表明6是一种非竞争性抑制剂，而30竞争性抑制酪氨酸酶。鲜切马铃薯片的抗褐变试验表明，6和30是有效的抗褐变剂，其能力与曲酸一样高。自由基清除和酪氨酸酶抑制的机制已在计算机中使用计算动力学、分子对接和分子动力学模拟进行了全面研究。

  DOI：

  10.1016/j.foodchem.2023.135745

文献信息

• Synthesis, Antibacterial Activity and Quantum-Chemical Studies of Novel 2-Arylidenehydrazinyl-4-arylthiazole Analogues
  作者：Mohammad Sayed Alam、Lijun Liu、Yong-Eok Lee、Dong-Ung Lee

  DOI：10.1248/cpb.59.568

  日期：——

  A new series of 2-arylidenehydrazinyl-4-arylthiazole derivatives (2a—k) was designed and synthesized through a rapid, simple, and efficient methodology in excellent isolated yield. These compounds were screened for in vitro antimicrobial activities against eight bacteria, e.g. Bacillus cereus, Staphylococcus aureus, Bacillus subtilis, Bacillus megaterium, Pseudomonas aeruginosa, Shigella dysenteriae, Salmonella typhi, Escherichia coli, and three fungi e.g. Aspergillus oryzae, Candida albicans, and Saccharomyces cerevis. The results indicate that some of the compounds exhibit strong antibacterial activity, depending on the bacterial strain, but show virtually no antifungal activity. The structure–antibacterial activity relationships were studied using some physicochemical and quantum-chemical parameters with the ab initio Hartree–Fock model at the RHF/6-31G level of theory. A good qualitative correlation between predicted lipophilic parameters and antibacterial activity has been found.

  通过快速、简单且高效的方法，设计并合成了一系列新的2-芳亚甲基酰肼-4-芳基噻唑衍生物（2a—k），这些化合物在极佳的分离产率下制得。我们对这些化合物进行了体外抗菌活性筛选，针对八种细菌（如蜡样芽孢杆菌、金黄色葡萄球球菌、枯草芽孢杆菌、巨大芽孢杆菌、铜绿假单胞菌、痢疾志贺菌、伤寒沙门菌、大肠埃希菌）和三种真菌（如米曲霉、白色念珠菌、酿酒酵母）进行了测试。结果显示，部分化合物根据细菌株的不同，展现出强烈的抗菌活性，但几乎不具备抗真菌活性。我们采用从头计算Hartree-Fock模型在RHF/6-31G理论水平上，利用一些物理化学和量子化学参数，研究了结构与抗菌活性之间的关系。发现预测的亲脂性参数与抗菌活性之间存在良好的定性相关性。
• Efficient one-pot three-component synthesis of N-(4-arylthiazol-2-yl) hydrazones in water under ultrasound irradiation
  作者：Dong-Nuan Zhang、Ji-Tai Li、Ya-Li Song、Hui-Min Liu、Hong-Ya Li

  DOI：10.1016/j.ultsonch.2011.10.017

  日期：2012.5

  A highly efficient and facile one-pot three-component synthesis of N-(4-arylthiazol-2-yl) hydrazones was carried out in excellent yield without any catalyst in water under ultrasound irradiation.

  N-（4-芳基噻唑-2-基）hydr的高效，便捷的一锅三组分合成法在超声波照射下在水中无催化剂的情况下以优异的收率进行。
• An investigation of the biological effect of structural modifications of isothiosemicarbazones and their cyclic analogues
  作者：E Maccioni、M.C Cardia、S Distinto、L Bonsignore、A De Logu

  DOI：10.1016/s0014-827x(03)00154-x

  日期：2003.9

  Several arylideneisothiosemicarbazones and arylidenehydrazothiazoles have been synthesised to obtain new antimicrobial agents. Their activity against both bacteria and fungi has been tested and some interesting informations about their biological activity have been obtained.
• Design, synthesis and biological evaluation of novel thiazole derivatives as potent FabH inhibitors
  作者：Peng-Cheng Lv、Kai-Rui Wang、Ying Yang、Wen-Jun Mao、Jin Chen、Jing Xiong、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2009.09.111

  日期：2009.12

  Fatty acid biosynthesis is essential for bacterial survival. Components of this biosynthetic pathway have been identified as attractive targets for the development of new antibacterial agents. FabH, beta-ketoacylacyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram positive and negative bacteria. Three series of Schiff bases containing thiazole template were synthesized and developed as potent inhibitors of FabH. This inhibitor class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 11 and 18 were potent inhibitors of E. coli FabH. (C) 2009 Elsevier Ltd. All rights reserved.
• Selective Inhibitory Activity against MAO and Molecular Modeling Studies of 2-Thiazolylhydrazone Derivatives
  作者：Franco Chimenti、Elias Maccioni、Daniela Secci、Adriana Bolasco、Paola Chimenti、Arianna Granese、Olivia Befani、Paola Turini、Stefano Alcaro、Francesco Ortuso、Maria C. Cardia、Simona Distinto

  DOI：10.1021/jm060869d

  日期：2007.2.1

  A series of 2-thiazolylhydrazone derivatives have been investigated for the ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) selectively. All of the compounds showed high activity against both the MAO-A and the MAO-B isoforms with pK(i) values ranging between 5.92 and 8.14 for the MAO-A and between 4.69 and 9.09 for the MAO-B isoforms. Both the MAO-A and the MAO-B isoforms, deposited in the Protein Data Bank as model 2BXR and 1GOS, respectively, were considered in a computational study performed with docking techniques on the most active and MAO-B-selective inhibitor, 18.