2-(3-ethoxy-4-hydroxybenzylidene)hydrazinecarbothioamide | 6324-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-ethoxy-4-hydroxybenzylidene)hydrazinecarbothioamide
• 英文别名: [(3-Ethoxy-4-hydroxyphenyl)methylideneamino]thiourea
• CAS: 6324-85-2
• 化学式: C₁₀H₁₃N₃O₂S
• mdl: MFCD01071037
• 分子量: 239.298
• InChiKey: CFEVJBPVXXAVRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-ethoxy-4-hydroxybenzylidene)hydrazinecarbothioamide 、 2-氯乙酰乙酸乙酯 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  In vitro and in silico antimalarial activity of 2-(2-hydrazinyl)thiazole derivatives

  摘要：

  A series of 2-(2-hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were synthesized, characterized and evaluated their inhibitory potentials against plasmodium falciparum, NF54, by in vitro blood stage assay. The compounds, ethyl-4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and 1-(4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidenelhydrazin-1-yl]-mu 3-thiazol-5-yliethan-1-one, 5d showed significant antimalarial activity with IC50 values of 0.725 mu M and 0.648 mu M respectively. To understand the mechanism, the binding interactions between 2-(2-hydrazinyl)thiazole derivatives and trans-2-enoyl acyl carrier protein reductase of P. falciparum were studied through docking studies. The half maximal inhibitory concentration (IC50) through docking studies for the compounds, 4d and 5d were found to be 22.88 mu M and 631.84 mu M respectively. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2013.11.001
• 作为产物：
  描述：

  乙基香兰素 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以82%的产率得到2-(3-ethoxy-4-hydroxybenzylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  一些新的4,5'-联苯并恶唑的合成与抗菌评价

  摘要：

  噻唑和联噻唑衍生物代表了抗菌药物发现中的普遍支架。因此，我们决定合成一些新的4,5'-双噻唑系列。总共合成了17种化合物，其结构解析基于元素分析（C，H，N，S）和光谱数据（MS和1 H NMR）。使用分光光度法评估了它们对几种革兰氏阳性和革兰氏阴性细菌菌株以及一种真菌菌株（白色念珠菌）的体外抗菌活性。一些化合物对革兰氏阴性大肠杆菌，鼠伤寒沙门氏菌和革兰氏阳性菌表现出中等至良好的抗菌活性。金黄色葡萄球菌和蜡状芽孢杆菌菌株。所有合成的化合物对白念珠菌均具有中度到很好的抑菌活性。

  DOI：

  10.1002/jhet.2054

文献信息

• Synthesis and Antimicrobial Evaluation of Some New 4,5′-Bisthiazoles
  作者：Tibor Rozsa、Mihaela Duma、Laurian Vlase、Ioana Ionuţ、Adrian Pîrnău、Brînduşa Tiperciuc、Ovidiu Oniga

  DOI：10.1002/jhet.2054

  日期：2015.7

  bisthiazole derivatives represent a prevalent scaffold in the antimicrobial drug discovery. Therefore, we have decided to synthesize some new series of 4,5′‐bisthiazoles. A total of 17 compounds were synthesized, their structural elucidation being based on elemental analysis (C,H,N,S) and spectroscopic data (MS and 1H NMR). Their in vitro antimicrobial activities were assessed against several Gram‐positive

  噻唑和联噻唑衍生物代表了抗菌药物发现中的普遍支架。因此，我们决定合成一些新的4,5'-双噻唑系列。总共合成了17种化合物，其结构解析基于元素分析（C，H，N，S）和光谱数据（MS和1 H NMR）。使用分光光度法评估了它们对几种革兰氏阳性和革兰氏阴性细菌菌株以及一种真菌菌株（白色念珠菌）的体外抗菌活性。一些化合物对革兰氏阴性大肠杆菌，鼠伤寒沙门氏菌和革兰氏阳性菌表现出中等至良好的抗菌活性。金黄色葡萄球菌和蜡状芽孢杆菌菌株。所有合成的化合物对白念珠菌均具有中度到很好的抑菌活性。
• Design, and synthesis of selectively anticancer 4-cyanophenyl substituted thiazol-2-ylhydrazones
  作者：Hasnain Mehmood、Mustapha Musa、Simon Woodward、Md Shahadat Hossan、Tracey D. Bradshaw、Muhammad Haroon、Andrew Nortcliffe、Tashfeen Akhtar

  DOI：10.1039/d2ra03226k

  日期：——

  concentrations. Cell cycle, caspase activation and Western blot assays demonstrated that compounds 3b′ and 3f induce cancer cell death via caspase-dependent apoptosis. The combination of straight forward synthesis and high activity makes the thiazoles 3 an interesting lead for further development.

  取代的缩氨基硫脲与 α-溴-4-氰基苯乙酮的环化允许快速单步可持续合成 4-氰基苯基-2-肼基噻唑文库（30 个例子，66-79%）。所有都显示出对 HCT-116 和 MCF-7 癌细胞系的抗癌功效，其中大多数比顺铂阳性对照更具活性。化合物 2-(2-(2-hydroxy-3-methylbenzylidene)hydrazinyl)-4-(4-cyanophenyl)thiazole ( 3f ) 和 2-(2-((pentafluorophenyl)methylene)-hydrazinyl)-4-(4 -氰基苯基)噻唑 ( 3a' ) 显示出针对 MCF-7 乳腺癌细胞的最佳 GI 50值（1.0 ± 0.1 μM 和 1.7 ± 0.3 μM）。抗结直肠癌HCT-116细胞，(2-(2-(3-bromothiophen-2-yl)methylene)hydrazinyl)-4-(
• In vitro and in silico antimalarial activity of 2-(2-hydrazinyl)thiazole derivatives
  作者：Parameshwar Makam、Prasoon Kumar Thakur、Tharanikkarasu Kannan

  DOI：10.1016/j.ejps.2013.11.001

  日期：2014.2

  A series of 2-(2-hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were synthesized, characterized and evaluated their inhibitory potentials against plasmodium falciparum, NF54, by in vitro blood stage assay. The compounds, ethyl-4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and 1-(4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidenelhydrazin-1-yl]-mu 3-thiazol-5-yliethan-1-one, 5d showed significant antimalarial activity with IC50 values of 0.725 mu M and 0.648 mu M respectively. To understand the mechanism, the binding interactions between 2-(2-hydrazinyl)thiazole derivatives and trans-2-enoyl acyl carrier protein reductase of P. falciparum were studied through docking studies. The half maximal inhibitory concentration (IC50) through docking studies for the compounds, 4d and 5d were found to be 22.88 mu M and 631.84 mu M respectively. (C) 2013 Elsevier B.V. All rights reserved.
• Pyridine appended 2-hydrazinylthiazole derivatives: design, synthesis, <i>in vitro</i> and <i>in silico</i> antimycobacterial studies
  作者：Ramkishore Matsa、Parameshwar Makam、Guneswar Sethi、Ahammed Ameen Thottasseri、Aswani Raj Kizhakkandiyil、Krishna Ramadas、Vignesh Mariappan、Agieshkumar Balakrishna Pillai、Tharanikkarasu Kannan

  DOI：10.1039/d2ra02163c

  日期：——

  Thirty novel pyridine-appended 2-hydrazinylthiazole derivatives have been synthesized and tested for their antimycobacterial activity against Mictrobactrium tuberculosis, H37Rv strain.

  已经合成了30种新的吡啶附加的2-肼基噻唑衍生物，并对它们在H37Rv菌株的抗结核活性进行了测试。