3'-chloroacetophenone thiosemicarbazone | 387847-12-3

• 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: 3'-chloroacetophenone thiosemicarbazone
• 英文别名: [1-(3-Chlorophenyl)ethylideneamino]thiourea；[1-(3-chlorophenyl)ethylideneamino]thiourea
• CAS: 387847-12-3
• 化学式: C₉H₁₀ClN₃S
• mdl: MFCD21101634
• 分子量: 227.718
• InChiKey: FOUDFBGIMTWDEF-UHFFFAOYSA-N

物化性质

• 沸点：
  360.4±44.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3'-chloroacetophenone thiosemicarbazone 、 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：

  氨基硫脲 、 3-氯苯乙酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 3'-chloroacetophenone thiosemicarbazone
  参考文献：
  名称：

  微波辅助合成新的噻唑并ros衍生物作为酪氨酸酶抑制剂和抗氧化剂

  摘要：

  在这项工作中，我们合成了一系列2-噻唑并hydr衍生物（1-27），并研究了它们作为酪氨酸酶抑制剂和抗氧化剂的生物学活性。一些化合物显示出强大的酪氨酸酶抑制活性，而4-（2-（2-（2-（1-（4-氨基苯基）亚乙基）-肼基）噻唑-4-基）苯酚（26）显示出比标准酪氨酸酶抑制剂曲酸更强的抑制作用。酸（IC 50：9.8μM对23.6μM）。化合物2，14，和26在2,2-二苯基-1-吡啶甲基肼基（DPPH）和2,2'-氮杂双（3-乙基苯并噻唑啉-6-磺酸）（ABTS）分析中显示出高抗氧化活性。结构-活性关系（SAR）表明，溴，羟基和氨基的取代对酪氨酸酶的抑制作用有很大影响。机理和动力学研究表明，化合物26作为可逆性和非竞争性抑制剂，对酪氨酸酶具有抑制作用。对接研究表明化合物26通过氢键与蘑菇酪氨酸酶强烈相互作用。

  DOI：

  10.1002/jhet.3760

文献信息

• Microwave‐assisted synthesis and biological evaluation of new thiazolylhydrazone derivatives as tyrosinase inhibitors and antioxidants
  作者：Yu Zhang、Xi Fu、Yangting Yan、Jinbing Liu

  DOI：10.1002/jhet.3760

  日期：2020.3

  In this work, we have synthesized a series of 2‐thiazolylhydrazone derivatives (1–27) and investigated their biological activities as tyrosinase inhibitors and antioxidants. Some compounds showed potent tyrosinase inhibitory activities and 4‐(2‐(2‐(1‐(4‐Aminophenyl)ethylidene)‐hydrazinyl)thiazol‐4‐yl) phenol (26) showed more potent inhibitory effect than the standard tyrosinase inhibitor kojic acid

  在这项工作中，我们合成了一系列2-噻唑并hydr衍生物（1-27），并研究了它们作为酪氨酸酶抑制剂和抗氧化剂的生物学活性。一些化合物显示出强大的酪氨酸酶抑制活性，而4-（2-（2-（2-（1-（4-氨基苯基）亚乙基）-肼基）噻唑-4-基）苯酚（26）显示出比标准酪氨酸酶抑制剂曲酸更强的抑制作用。酸（IC 50：9.8μM对23.6μM）。化合物2，14，和26在2,2-二苯基-1-吡啶甲基肼基（DPPH）和2,2'-氮杂双（3-乙基苯并噻唑啉-6-磺酸）（ABTS）分析中显示出高抗氧化活性。结构-活性关系（SAR）表明，溴，羟基和氨基的取代对酪氨酸酶的抑制作用有很大影响。机理和动力学研究表明，化合物26作为可逆性和非竞争性抑制剂，对酪氨酸酶具有抑制作用。对接研究表明化合物26通过氢键与蘑菇酪氨酸酶强烈相互作用。
• 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.