(E)-2-(2-chlorobenzylidene)hydrazine-1-carbothioamide | 186507-05-1

• 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: (E)-2-(2-chlorobenzylidene)hydrazine-1-carbothioamide
• 英文别名: (E)-2-chlorobenzaldehyde thiosemicarbazone；2-chlorobenzaldehyde thiosemicarbazone；(E)-1-(2-chlorobenzylidene)thiosemicarbazide；[(E)-(2-chlorophenyl)methylideneamino]thiourea
• CAS: 186507-05-1
• 化学式: C₈H₈ClN₃S
• mdl: MFCD00022154
• 分子量: 213.691
• InChiKey: ZGPJVXICCFYSRT-VZUCSPMQSA-N

物化性质

• 熔点：
  215 °C (decomp)
• 沸点：
  351.9±44.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (E)-2-(2-chlorobenzylidene)hydrazine-1-carbothioamide 、 2-氯乙酰乙酸乙酯 以 乙醇 为溶剂， 以83%的产率得到ethyl 2-[(E)-2-[(2-chlorophenyl)methylidene]hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  2-(2-Hydrazinyl)thiazole derivatives: Design, synthesis and in vitro antimycobacterial studies

  摘要：

  In an attempt to discover new potent inhibitors for Mycobacterium tuberculosis (Mtb), a series of 2-(2hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were designed by considering Lipinski rule. The designed compounds were synthesized, characterized and evaluated for their inhibitory potential against Mtb, H(37)Rv, by in vitro assay. The compounds, ethyl-4methyl-2-[(E)-24]-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and ethyl-2[(E)-2-[(2-hydroxyphenyl)methylidenelhydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate, 2i showed noticeable inhibitory activity against Mtb, H37Rv with minimum inhibitory concentration (MIC) of 12.5 pM and 25 1.1M respectively. An attempt has been made to understand the mechanism of action by binding interactions of these molecules with 0-ketoacyl-ACP synthase protein through docking studies. The inhibition constants for compounds 4d and 2i were found to be 1.46 pM and 0.177 pM respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.054
• 作为产物：
  描述：

  2-氯苯甲醛 、 氨基硫脲 在 四氢吡咯 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (E)-2-(2-chlorobenzylidene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  在温和的有机催化反应条件下可持续合成肟，Hy和硫代氨基脲

  摘要：

  吡咯烷很有效地催化，大概是通过亚胺基活化，使用等摩尔量的试剂和绿色溶剂，形成了芳香族和脂肪族醛衍生的酰基肟，酰基hydr和硫代半氨基甲酮。该方法的主要优点是实验简单，过滤简单后的优异收率，是目前可用于那些特别是酰基衍生物的替代方法，这些方法在未催化条件下不起作用。通过醛和酰基羟胺之间的直接缩合将其用于合成酰基肟的应用是空前的。

  DOI：

  10.1021/acs.joc.6b01912

文献信息

• Design, Synthesis, and Evaluation of 3-((4-(<i>t</i>-Butyl)-2-(2-benzylidenehydrazinyl)thiazol-5-yl)methyl)quinolin-2(1<i>H</i>)-ones as Neuraminidase Inhibitors
  作者：Yilin Fang、Mengwu Xiao、Aixi Hu、Jiao Ye、Wenwen Lian、Ailin Liu

  DOI：10.1002/cjoc.201500738

  日期：2016.4

  A series of novel 3‐((4‐(t‐butyl)‐2‐(2‐benzylidenehydrazinyl)thiazol‐5‐yl)methyl)quinolin‐2(1H)‐ones (7a–7z) were designed, synthesized and evaluated for their ability of inhibiting neuraminidase (NA) of in?uenza H1N1 virus. Some compounds displayed moderate influenza NA inhibitory activity. Compound 7l with the scaffold of 2‐(2‐(2‐methoxybenzylidene)hydrazinyl)thiazole was the best one, exhibiting

  设计，合成和合成了一系列新颖的3-（（4-（叔丁基）-2-（2-苄叉肼基）噻唑-5-基）甲基）喹啉-2-（1 H）-酮（7a - 7z）评估其抑制流感H1N1病毒神经氨酸酶（NA）的能力。一些化合物显示出中等的流感NA抑制活性。带有7-（2-（2-（2-甲氧基亚苄基）肼基）噻唑骨架的化合物7l是最好的化合物，具有中等的NA抑制活性，IC 50为44.66 µmol / L。结构-活性关系显示出与甲氧基或羟基基团的化合物在邻位，氟和硝基在元苯环对位的氯和溴基更活泼。对接研究表明，化合物7l与一些关键残基（包括Asp151，Glu119，Arg292，Tyr406和Asn347）具有重要的相互作用，并与邻近NA活性位点的430腔结合。
• Halogenated aromatic thiosemicarbazones as potent inhibitors of tyrosinase and melanogenesis
  作者：Katarzyna Hałdys、Waldemar Goldeman、Michał Jewgiński、Ewa Wolińska、Natalia Anger-Góra、Joanna Rossowska、Rafał Latajka

  DOI：10.1016/j.bioorg.2019.103419

  日期：2020.1

  been synthesized and its inhibitory properties toward activity diphenolase of mushroom tyrosinase and their ability to inhibition of melanogenesis in B16F10 murine, melanoma cell line have been investigated. The molecular docking to the active site of the enzyme has been also performed to investigate the nature of enzyme-inhibitor interactions. The obtained outcomes allowed us to perform SAR analysis

  已经合成了一组21个卤代硫代半氨基甲酮（TSC），并研究了其对蘑菇酪氨酸酶活性双酚酶的抑制特性以及它们在B16F10小鼠黑素瘤细胞系中抑制黑素生成的能力。还进行了与酶活性位点的分子对接，以研究酶-抑制剂相互作用的性质。获得的结果使我们能够进行SAR分析。TSC 6、12和21表现出最强的抑制特性，IC50分别为0.5、0.9和0.8 µM。他们揭示了酪氨酸酶抑制作用的可逆性和竞争性方式。根据SAR分析，在所研究的化合物中，硫代半氨基甲酮的对位取代的苯乙酮衍生物对该酶具有最高的亲和力。B16F10细胞中黑色素的产生被所有研究的化合物以微摩尔水平抑制。建议的抑制机理是基于硫代半氨基甲酮的硫脲部分的硫原子与酶活性位点中的铜离子之间的相互作用。这些结果可能有助于寻找可用于化妆品和食品工业的新型黑色素生成抑制剂。
• Synthesis, spectroscopic characterization, single crystal XRD, Hirshfeld Surface analysis and theoretical studies (DFT) of 4-adamantyl-(2-(substitutedbenzylidene)hydrazinyl)thiazoles
  作者：Yasir Iqbal、Muhammad Haroon、Tashfeen Akhtar、Muhammad Ashfaq、Muhammad Nawaz Tahir、Lubna Rasheed、Muhammad Yousuf、Muhammad Abid Zia

  DOI：10.1016/j.molstruc.2022.133620

  日期：2022.11

  moderate one. We have also compared the theoretical molecular vibrations and chemical shifts of the compounds with experimental data and results were in good agreement with each other. On the basis of respective correlation co-efficient (σ2) of calculation methods (6-311G(d,p), ccPVTZ and ccPVDZ) it is revealed that ccPVTZ basis sets gave the best results. The MEP analysis revealed that electronegative elements

  在目前的工作中，通过1-（取代的亚苄基）氨基硫脲(2)和 1-金刚烷基溴甲基酮的简单环化反应合成了两种新型的金刚烷基噻唑类化合物。在光谱分析技术的帮助下确定了所得化合物3a和3b的结构，例如：FTIR, 1 H-, 13C-NMR和质谱。结构的最终确认是用单晶 XRD 完成的。使用密度泛函理论 (DFT) 进一步研究了化合物的所有光谱特性。量子化学计算采用 B3LYP 方法，以 6-311G(d,p)、ccPVTZ 和 ccPVDZ 为基组，确定键长、键角、二面角、前沿分子轨道 (FMO) 和分子静电势 (MEP)，这表明分子3b是强亲电体，而分子3a是中等亲电体。我们还将化合物的理论分子振动和化学位移与实验数据进行了比较，结果相互吻合。基于各自的相关系数（σ2 )的计算方法(6-311G(d,p)、ccPVTZ和ccPVDZ)表明ccPVTZ基组给出了最好的结果。MEP分析表明，结构中的电负性元素拥有最大的电子云。
• Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors
  作者：Muhammad Adil S. Aslam、Shams-ul Mahmood、Mohammad Shahid、Aamer Saeed、Jamshed Iqbal

  DOI：10.1016/j.ejmech.2011.09.009

  日期：2011.11

  A series of new and novel Schiff base derivatives were synthesized and investigated as potential new inhibitors of Jack bean urease. The most potent compounds were 3f with (K-i = 0.09 mu M) and 3k (K-i = 0.122 mu M). A pure competitive mechanism of inhibition was observed. Molecular docking studies were also performed to illustrate the binding mode of the compounds. Docking studies were performed on both enzymes from Jack bean urease and H. pylori urease. It was observed that both share the same binding mode. The binding sites of the two urease structures also aligned very well indicating the similarity in binding sites of the enzymes. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis and Biological Evaluation of 3-thiazolocoumarinyl Schiff-base Derivatives as Cholinesterase Inhibitors
  作者：Rabia Raza、Aamer Saeed、Mubeen Arif、Shamsul Mahmood、Muhammad Muddassar、Ahsan Raza、Jamshed Iqbal

  DOI：10.1111/j.1747-0285.2012.01435.x

  日期：2012.10

  On the basis of the observed biological activity of the coumarins, a new set of 3‐thiazolocoumarinyl Schiff‐base derivatives with chlorine, hydroxy and methoxy functional group substitutions were designed and synthesized. These compounds were tested against acetylcholinesterase from Electrophorus electricus and butyrylcholinesterase from horse serum and their structure–activity relationship was established. Studies revealed them as the potential inhibitors of cholinesterase (acetylcholinesterase and butyrylcholinesterase). The 3f was found to be most potent against acetylcholinesterase with Ki value of 1.05 ± 0.3 μm and 3l showed excellent inhibitory action against butyrylcholinesterase with Ki value of 0.041 ± 0.002 μm. The synthesized compounds were also docked into the active sites of the homology models of acetylcholinesterase and butyrylcholinesterase to predict the binding modes of these compounds. It was predicted that most of the compounds have similar binding modes with reasonable binding affinities. Our docking studies have also shown that these synthesized compounds have better interaction patterns with butyrylcholinesterase over acetylcholinesterase. The main objective of the study was to develop new potent and selective compounds, which might be further optimized to prevent the progression of the Alzheimer’s disease and could provide symptomatic treatment.