2-(2-cyclopentylidenehydrazinyl)-4-phenyl-1,3-thiazole

• 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-cyclopentylidenehydrazinyl)-4-phenyl-1,3-thiazole
• 英文别名: 2-(2-cyclopentylidenehydrazineyl)-4-phenylthiazole；2-(2-cyclopentylidenehydrazinyl)-4-phenylthiazole；N-(cyclopentylideneamino)-4-phenyl-1,3-thiazol-2-amine
• 化学式: C₁₄H₁₅N₃S
• mdl: MFCD01113275
• 分子量: 257.359
• InChiKey: WUSIIHCESPBBHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2-溴苯乙酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 2-(2-cyclopentylidenehydrazinyl)-4-phenyl-1,3-thiazole
  参考文献：
  名称：

  在无溶剂条件下通过三组分反应一锅法快速合成 2,4-二取代噻唑

  摘要：

  摘要开发了一种快速的一锅法，用于在无溶剂条件下通过多组分方法合成 2,4-二取代噻唑。通过环酮、氨基硫脲和苯甲酰溴或3-(2-溴乙酰)-2H-色烯-2-酮在较短的反应时间内反应，通过简单的纯化技术以高产率合成取代的噻唑。图形概要

  DOI：

  10.1080/00397911.2017.1399422

文献信息

• Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: Enzyme and cellular studies
  作者：Simone Carradori、Dante Rotili、Celeste De Monte、Alessia Lenoci、Melissa D'Ascenzio、Veronica Rodriguez、Patrizia Filetici、Marco Miceli、Angela Nebbioso、Lucia Altucci、Daniela Secci、Antonello Mai

  DOI：10.1016/j.ejmech.2014.04.042

  日期：2014.6

  thiazolidines and pyrimidin-4(3H)-ones, and we tested the whole library existing in our lab against human p300 and PCAF HAT enzymes. Some compounds (1x, 1c', 1d', 1i' and 2m) were more efficient than CPTH2 and CPTH6 in inhibiting the p300 HAT enzyme. When tested in human leukemia U937 and colon carcinoma HCT116 cells (100 μM, 30 h), 1x, 1i' and 2m gave higher (U937 cells) or similar (HCT116 cells) apoptosis

  最近，我们描述了一些（噻唑-2-基）azo作为抗原生动物，抗真菌和抗MAO试剂以及Gcn5 HAT抑制剂。在这些最后的化合物中，CPTH2和CPTH6在细胞中显示出HAT抑制作用和广泛的抗癌特性。为了鉴定比两个原型更有效的HAT抑制剂，我们合成了几种新的（噻唑-2-基）azo酮，包括一些相关的噻唑烷和嘧啶4（3 H）-酮，并测试了我们现有的整个文库针对人p300和PCAF HAT酶的实验室。某些化合物（1x，1c '，1d '，1i '和2m）在抑制p300 HAT酶方面比CPTH2和CPTH6更有效。在人白血病U937和结肠癌HCT116细胞（100μM，30小时）中进行测试时，1x，1i '和2m产生的凋亡（U937细胞）或类似细胞（HCT116细胞）高于CPTH6，并且在诱导细胞分化方面比CPTH6更有效（U937细胞）。
• 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 Efficient Method for the One‐pot Synthesis of 4‐Phenyl‐hydrazinyl Thiazole Derivatives Using Nano‐SiO₂
  作者：Sahar Gholami、Masoud Mokhtary

  DOI：10.1002/jhet.3371

  日期：2018.12

  One‐pot synthesis of 4‐phenyl‐hydrazinyl thiazole derivatives was developed by three‐component reaction of various ketones, phenacyl chloride, and thiosemicarbazid in the presence of nano‐SiO2 in ethanol at reflux conditions. The products formed in excellent yields over short reaction times under an environmentally friendly condition.

  在乙醇中存在纳米SiO 2的条件下，通过各种酮，苯甲酰氯和硫代氨基脲的三组分反应，开发了4-苯基-肼基噻唑衍生物的一锅法合成方法。在环境友好的条件下，在短的反应时间内以优异的产率形成了产物。
• Dry Grinding Synthesis and Docking Study of Cyclopentanone-Sulfur Containing Compounds with Anti-Proliferative Activity for HepG-2 and A-549 Cancer Cell Lines
  作者：Thoraya A. Farghaly、Zeinab A. Muhammad、Sami A. Al-Hussain、Mastoura M. Edrees、Magdi E. A. Zaki、Sara N. Shabaan

  DOI：10.2174/1573406418666220324155119

  日期：2022.12

  The dry grinding method is a green technique for efficient organic synthesis with numerous advantages, such as mild reaction conditions, environmental acceptability, simple segregation, and refinement, as well as elevated selectivity and efficiency.

  The aim of the present work is to design and synthesize cyclopentylidene-hydrazino)- thiazole derivatives using dry grinding conditions to investigate their antitumor activity against two cell lines, namely, HepG-2 and A-549.

  In this context, we synthesized a series of thiazole incorporated cyclopentane through hydrazone- group and 2-cyclopentylidenehydrazine-1-carbimidic-2-ethoxy-N-aryl-2-oxoacetohydrazonic thioanhydride under dry grinding within minutes and excellent to good yield.

  All spectral data confirmed the proposed structures. In addition to antitumor activity investigations against the two kinds of cancer cells, molecular docking studies were conducted using Macrophage Migration Inhibitory Factor (Pdb: 4k9g) and Lysozyme C (Pdb: 2f4a), the overexpressed proteins in the human liver cancer cell (HepG-2) and lung cancer cell lines (A-549), respectively.

  Two derivatives, 9b, and 9d, showed the highest antitumor activity against the two cell lines HepG-2 and A-549. Also, docking results revealed a high energy score ranging from -7.1590 to -5.9364 Kcal/mol with Macrophage Migration Inhibitory Factor (Pdb: 4k9g), more than that the energy score = -4.118 Kcal/mol of co-crystallized ligand. Moreover, the tested derivatives showed energy score varies from -6.0802 to -4.5503 Kcal/mol against Lysozyme C (Pdb: 2f4a).

  背景： 干磨法是一种高效有机合成的绿色技术，具有许多优点，如温和的反应条件、环境可接受性、简单的分离和精制、以及升高的选择性和效率。 目标：本研究的目的是设计和合成环戊基亚甲基-肼)-噻唑类衍生物，使用干磨条件研究它们对两种细胞系（HepG-2和A-549）的抗肿瘤活性。 方法：在这种情况下，我们通过肼酰基和2-环戊基亚甲基肼-1-氨基甲酸酯-2-乙氧基-N-芳基-2-氧代乙酰肼基硫酸酐在几分钟内使用干磨法合成了一系列噻唑并环戊烷，产率良好。 结果：所有光谱数据都证实了所提出的结构。除了抗肿瘤活性研究外，还进行了分子对接研究，使用宏噬细胞迁移抑制因子（Pdb: 4k9g）和溶菌酶C（Pdb: 2f4a）进行了分子对接研究，它们是人类肝癌细胞（HepG-2）和肺癌细胞系（A-549）中过度表达的蛋白质。 结论：两种衍生物，9b和9d，对两种细胞系HepG-2和A-549显示出最高的抗肿瘤活性。此外，对接结果显示，与结晶配体的能量得分-4.118 Kcal/mol相比，与宏噬细胞迁移抑制因子（Pdb: 4k9g）的能量得分范围为-7.1590至-5.9364 Kcal/mol更高。此外，测试的衍生物对溶菌酶C（Pdb: 2f4a）的能量得分在-6.0802至-4.5503 Kcal/mol之间变化。
• 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.