p-dimethylaminobenzaldehyde thiosemicarbazone | 2929-81-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: p-dimethylaminobenzaldehyde thiosemicarbazone
• 英文别名: (E)-2-(4-(dimethylamino)benzylidene)hydrazinecarbothioamide；(2E)-2-{[4-(dimethylamino)phenyl]methylidene}-hydrazine-1-carbothioamide；4-(Dimethylamino)benzaldehyde thiosemicarbazone；[(E)-[4-(dimethylamino)phenyl]methylideneamino]thiourea
• CAS: 2929-81-9
• 化学式: C₁₀H₁₄N₄S
• 分子量: 222.314
• InChiKey: MUDHKEQEBJQRRG-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  85.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  p-dimethylaminobenzaldehyde thiosemicarbazone 在 碳酸氢钠 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 [Ni((2E)-2-[4-(dimethylamino)benzylidene]-N-[(1Z,2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydrazinecarbothioamide)₂]
  参考文献：
  名称：

  Synthesis, characterization, and in vitro anti-neoplastic activity of novel vic-dioximes bearing thiosemicarbazone side groups and their mononuclear complexes

  摘要：

  Two novel vicinal dioxime ligands containing thiosemicarbazone units, (2E)-2-[4-(diethylamino)benzylidene]-N-[(1Z, 2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydrazine carbothioamide ((LH2)-H-1) and (2E)-2-[4-(dimethylamino)benzylidene]-N-[(1Z,2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydra-zinecarbothioamide ((LH2)-H-2), were synthesized. Using the HL-60 human leukemia cell line, the in vitro anti-neoplastic activity of these thiosemicarbazone-oxime derivatives was evaluated. Mononuclear nickel(II), copper(II), and cobalt(II) complexes with a metal: ligand ratio of 1:2 for both the (LH2)-H-1 and (LH2)-H-2 ligands were also synthesized. To characterize these compounds, Fourier transform-infrared spectroscopy (FT-IR), mass spectrometry (MS), magnetic susceptibility measurements, H-1 and C-13 nuclear magnetic resonance (NMR), ultraviolet-visible (UV-Vis) absorption spectroscopy, heteronuclear multiple-bond correlation (HMQC), and elemental analysis were performed. For (LH2)-H-1, (LH2)-H-2, and each of their derivatives, antiproliferative effects against HL-60 cells were exhibited and the associated IpC50 values ranged from 5 mu M to 20 mu M. Furthermore, (LH2)-H-1 and its derivatives inhibited the proliferation of HL-60 cells more effectively than (LH2)-H-2, and 5 mu M [Cu((LH)-H-1)(2)] exhibited the strongest antiproliferative activity. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.01.003
• 作为产物：
  描述：

  氨基硫脲 、 对二甲氨基苯甲醛 以 乙醇 、 水 为溶剂， 反应 2.5h， 以93%的产率得到p-dimethylaminobenzaldehyde thiosemicarbazone
  参考文献：
  名称：

  广谱抗病毒活性，包括由新型维甲酸类硫代半乳糖胺衍生物介导的人类免疫缺陷和丙型肝炎病毒

  摘要：

  芳香醛衍生的缩氨基硫脲4 - 6，该小号-取代的缩氨基硫脲改性7 / 8，和维生素A衍生的（类视黄醇）缩氨基硫脲衍生物12进行了调查人类C型肝炎病毒的抑制剂（HCV）亚基因组RNA复制子的Huh7 ET（luc的-ubi-neo / ET）复制。化合物4 - 6和12被认为是HCV RNA复制子复制的有效抑制剂。三氟甲氧基取代的硫代氨基脲6和类维生素A硫代氨基脲衍生物12它们的选择性甚至优于所含参考试剂重组人α-干扰素2b，显示出在纳摩尔浓度范围内的效力。此外，化合物5，6，8和12进行了测试作为由水痘带状疱疹病毒（VZV）和/或人巨细胞病毒（HCMV）诱导的细胞病变效应（CPE）的抑制剂。化合物4 - 6，8和12被附加地检查如牛痘病毒和牛痘病毒诱导的CPE的抑制剂。硫代氨基脲4与参考药物西多福韦相比，其对牛痘和牛痘病毒复制的抑制作用在效力和选择性上可比。类维生素A硫半碳环酮衍生物12作

  DOI：

  10.1016/j.ejmech.2011.02.014

文献信息

• Synthesis, NMR structural characterization and molecular modeling of substituted thiosemicarbazones and semicarbazones using DFT calculations to prove the syn/anti isomer formation
  作者：T. K. Venkatachalam、Gregory K. Pierens、David C. Reutens

  DOI：10.1002/mrc.4041

  日期：2014.3

  Thiosemicarbazones possessing electron‐donating and electron‐withdrawing groups were prepared, and their spectral characteristics determined. In all cases, the spectra showed that one isomer was formed, allowing further functionalization to molecules of biological interest. We provide NMR data for some of the thiosemicarbazones and semicarbazones. We also provide evidence that for 2‐pyridyl thiosemicarbazone

  制备了具有给电子和吸电子基团的硫缩氨基脲，并确定了它们的光谱特性。在所有情况下，光谱都表明形成了一种异构体，从而可以进一步功能化具有生物学意义的分子。我们提供了一些缩氨基硫脲和缩氨基脲的核磁共振数据。我们还提供证据表明，对于 2-吡啶基缩氨基硫脲，顺式异构体在二甲亚砜溶剂中以一级动力学缓慢转化为反式异构体。分子建模和密度泛函理论计算证实了这些观察结果。版权所有 © 2014 John Wiley & Sons, Ltd.
• Aryl hydrazones linked thiazolyl coumarin hybrids as potential urease inhibitors
  作者：Uzma Salar、Bakhtawer Qureshi、Khalid Mohammed Khan、Muhammad Arif Lodhi、Zaheer Ul‑Haq、Farman Ali Khan、Fouzia Naz、Muhammad Taha、Shahnaz Perveen、Shafqat Hussain

  DOI：10.1007/s13738-021-02377-8

  日期：2022.4

  Aryl hydrazones bearing thiazolyl coumarin hybrids 1–32 were prepared by following 'one-pot' two-steps reaction scheme. Various arylaldehydes were reacted to thiosemicarbazide under acidic condition to form aryl thiosemicarbazone intermediates which in turn treated with 3-bromoacetyl coumarin under basic condition to afford thiazolyl coumarin hybrids 1–32. All hybrids were recognized by EI- and HREI-MS

  通过遵循“一锅”两步反应方案制备带有噻唑基香豆素杂化物1-32的芳基腙。各种芳醛在酸性条件下与氨基硫脲反应形成芳基氨基氨基硫脲中间体，该中间体又在碱性条件下用 3-溴乙酰香豆素处理，得到噻唑基香豆素杂化物 1-32。所有杂种均通过 EI-和 HREI-MS 以及 1H-和 13C-NMR 光谱技术进行识别。筛选化合物 1-32 对脲酶的体外抑制活性，并在 IC50 = 16.29 ± 1.1-256.30 ± 1.4 µM 范围内显示出良好至中等的抑制潜力。值得指出的是，化合物 21 (IC50 = 16.29 ± 1.1 µM) 被确定为比标准乙酰氧肟酸 (IC50 = 27.0 ± 0.5 µM) 更有效的脲酶抑制剂。衍生物 19 (IC50 = 77.67 ± 1. 5 µM) 和 30 (IC50 = 71.21 ± 1.6 µM) 被发现具有中度活性。构效关系表明-F、-Cl、-
• A Series of Benzylidenes Linked to Hydrazine‐1‐carbothioamide as Tyrosinase Inhibitors: Synthesis, Biological Evaluation and Structure−Activity Relationship
  作者：Hona Hosseinpoor、Aida Iraji、Najmeh Edraki、Somayeh Pirhadi、Mahshid Attarroshan、Mahsima Khoshneviszadeh、Mehdi Khoshneviszadeh

  DOI：10.1002/cbdv.202000285

  日期：2020.8

  and enzymatic browning of vegetables and fruits. In the present article, 12 small molecules of benzylidene-hydrazinecarbothioamide were designed, synthesized and evaluated for their anti-tyrosinase activities followed by molecular docking and pharmacophore-based screening. Among synthesized thiosemicarbazone derivatives, 3d is the strongest inhibitor of mushroom tyrosinase with IC 50 of 0.05 µM which

  酪氨酸酶是一种 3 型铜酶，可导致皮肤色素沉着障碍、皮肤癌以及蔬菜和水果的酶促褐变。在本文中，设计、合成了 12 个小分子亚苄基肼碳硫酰胺并评估了它们的抗酪氨酸酶活性，然后进行了分子对接和基于药效团的筛选。在合成的氨基硫脲衍生物中，3d 是最强的蘑菇酪氨酸酶抑制剂，IC 50 为 0.05 µM，与阳性对照相比，其效力提高了 128 倍。动力学研究还揭示了 3d 的混合类型抑制。对接研究证实合成的化合物完全适合酪氨酸酶活性位点。
• Synthesis, computational studies and enzyme inhibitory kinetics of substituted methyl[2-(4-dimethylamino-benzylidene)-hydrazono)-4-oxo-thiazolidin-5-ylidene]acetates as mushroom tyrosinase inhibitors
  作者：Pervaiz Ali Channar、Aamer Saeed、Fayaz Ali Larik、Muhammad Rafiq、Zaman Ashraf、Farukh Jabeen、Tanzeela Abdul Fattah

  DOI：10.1016/j.bmc.2017.09.009

  日期：2017.11

  The present article describes the synthesis and enzyme inhibitory kinetics of methyl[2-(arylmethylene-hydrazono)-4-oxo-thiazolidin-5-ylidene]acetates 5a–j as mushroom tyrosinase inhibitors. The title compounds were synthesized via cyclocondensation of thiosemicarbazones 3a–j with dimethyl but-2-ynedioate (DMAD) 4 in good yields under solvent-free conditions. The synthesized compounds were evaluated

  本文描述了作为蘑菇酪氨酸酶抑制剂的甲基[2-（芳基亚甲基-肼基）-4-氧代-噻唑烷-5--5-亚甲基]乙酸酯5a – j的合成和酶抑制动力学。标题化合物是在无溶剂条件下，以高收率通过硫代半咔唑3a – j与丁-2-炔二酸二甲酯（DMAD）4的环缩合反应合成的。评价合成的化合物抑制蘑菇酪氨酸酶活性的潜力。据透露，化合物5i在IC 50为3.17 µM时显示出优异的酶抑制活性，而IC 50为标准曲酸的浓度为15.91 µM。化合物5i中杂环吡啶环的存在在酶抑制活性中起重要作用，因为所有合成的化合物中其余的官能团都是常见的。通过Lineweaver-Burk图和Dixon图确定的最有效衍生物5i的酶抑制动力学表明，它是与Ki不竞争的抑制剂值1.5 µM。进一步研究表明，湿实验室的结果与计算结果非常吻合。对酪氨酸酶蛋白（PDBID 2Y9X）进行合成化合物的分子对接，以在分子水平上描述配体-蛋白相
• On the verification of binding modes of p-dimethylaminobenzaldehyde thiosemicarbazone with mercury(II). The solid state studies
  作者：Agata Trzesowska-Kruszynska

  DOI：10.1016/j.molstruc.2014.05.027

  日期：2014.8

  thiosemicarbazone, fluorescent chemosensor, have been synthesised from the mercury(II) nitrate and mercury(II) chloride, and subsequently characterised by IR spectroscopy, thermal analysis, as well as single crystal X-ray diffraction technique. The inorganic anion has a distinct influence on binding mode of thiosemicarbazone ligand to Hg(II) ion. In both compounds the metal to ligand stoichiometry is 1:2 and

  摘要 以硝酸汞（II）和氯化汞（II）为原料合成了对二甲氨基苯甲醛缩氨基硫脲的两种配位化合物，并通过红外光谱、热分析和单晶X射线衍射技术进行了表征。 . 无机阴离子对氨基硫脲配体与 Hg(II) 离子的结合方式有明显影响。在这两种化合物中，金属与配体的化学计量比为 1:2，有机配体与中性硫酮形式的 Hg 离子配位，但它们的配体结合模式和配体构象不同。硝酸汞 (II) 与氨基硫脲络合物的晶体堆积受汞螯合环-亚苯基环 π … π 堆积相互作用控制。