1-cyclopentylidene-2-(4-(4-methoxyphenyl)thiazol-2-yl)hydrazine | 949912-57-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-cyclopentylidene-2-(4-(4-methoxyphenyl)thiazol-2-yl)hydrazine
• 英文别名: 2-(2-Cyclopentylidenehydrazinyl)-4-(4-methoxyphenyl)thiazole；N-(cyclopentylideneamino)-4-(4-methoxyphenyl)-1,3-thiazol-2-amine
• CAS: 949912-57-6
• 化学式: C₁₅H₁₇N₃OS
• 分子量: 287.385
• InChiKey: XHYZSHVRUWFCNJ-UHFFFAOYSA-N

物化性质

• 熔点：
  196-197 °C
• 沸点：
  467.7±47.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环戊酮 在 盐酸 、 三乙胺 作用下， 以 水 为溶剂， 反应 0.37h， 生成 1-cyclopentylidene-2-(4-(4-methoxyphenyl)thiazol-2-yl)hydrazine
  参考文献：
  名称：

  Dry Grinding Synthesis and Docking Study of Cyclopentanone-Sulfur Containing Compounds with Anti-Proliferative Activity for HepG-2 and A-549 Cancer Cell Lines

  摘要：

  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。

  DOI：

  10.2174/1573406418666220324155119

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）。
• Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring
  作者：S.K. Bharti、G. Nath、R. Tilak、S.K. Singh

  DOI：10.1016/j.ejmech.2009.11.008

  日期：2010.2

  antimicrobial activities. The structures of synthesized compounds were established by spectroscopic (FT-IR, 1H NMR, 13C NMR, Mass) and elemental analyses. Both the anti-bacterial and anti-fungal activities with MIC values of compounds were evaluated. The results of anti-bacterial screening reveal that among all the compounds screened eight compounds showed moderate to good anti-bacterial activity while ten

  一系列的亚芳基-2-（4-（4-（4-甲氧基/溴苯基）噻唑-2-基）肼（4a – z）和1-（4-（4-甲氧基/溴苯基）噻唑-2-基）-2合成了-cyclohexydenne / cyclopentylidene肼（5a – b / 6a – b），并对其抗菌性能进行了表征和筛选。通过光谱（FT-IR，1 H NMR，1313 C NMR，质量）和元素分析。用化合物的MIC值评估了抗菌和抗真菌活性。抗菌筛选结果表明，在筛选出的所有化合物中，有八种化合物表现出中等至良好的抗菌活性，而新合成的化合物中有十种表现出良好至优异的抗真菌活性。在测试的化合物中，MIC值在6.25–25μg/ ml范围内的最有效化合物是针对三种真菌菌株viz的4a，4n，4z，5a，5b，6a和6b。白色念珠菌，新型隐球菌和黄曲霉。
• Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
  作者：Franco Chimenti、Bruna Bizzarri、Elias Maccioni、Daniela Secci、Adriana Bolasco、Rossella Fioravanti、Paola Chimenti、Arianna Granese、Simone Carradori、Daniela Rivanera、Daniela Lilli、Alessandra Zicari、Simona Distinto

  DOI：10.1016/j.bmcl.2007.05.078

  日期：2007.8

  In this paper, we report on the synthesis of a novel series of 2-thiazolylhydrazone derivatives and the influence of the substituents on the thiazole ring on antifungal activity. All synthesized compounds were screened for their in vitro activities against 22 clinical isolates of Candida spp., representing six different species, compared to clotrimazole as a reference compound. Some of the tested compounds were found to possess significant antifungal activity when compared to clotrimazole, in particular compound 14 which exhibited higher potency against most of the Candida spp. considered. The compounds that were most active as anti-Candida agents were also Submitted to cytotoxic screening by the Trypan Blue dye exclusion assay and in general they were shown to induce low cytotoxic effects. (c) 2007 Elsevier Ltd. All rights reserved.
• 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。