(E)-2-(2,3-dihydroxybenzylidene)hydrazinecarbothioamide | 7411-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-2-(2,3-dihydroxybenzylidene)hydrazinecarbothioamide
• 英文别名: N-(2,3-dihydroxybenzylidene)thiosemicarbazide；(2E)-2-[(2,3-dihydroxyphenyl)methylidene]-hydrazine-1-carbothioamide；(E)-2-(2,3-dihydroxybenzylidene)hydrazine-1-carbothioamide；2,3-dihydroxy-benzaldehyde-thiosemicarbazone；2,3-Dihydroxy-benzaldehyd-thiosemicarbazon；[[(E)-(5-hydroxy-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino]thiourea；[(E)-(2,3-dihydroxyphenyl)methylideneamino]thiourea
• CAS: 7411-05-4
• 化学式: C₈H₉N₃O₂S
• 分子量: 211.244
• InChiKey: BBAULBCUTURIMD-ONNFQVAWSA-N

物化性质

• 熔点：
  206.0-207.6 °C
• 沸点：
  427.6±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(2,3-dihydroxybenzylidene)hydrazinecarbothioamide 、 magnesium acetate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Investigation of the salicylaldehyde thiosemicarbazone scaffold for inhibition of influenza virus PA endonuclease

  摘要：

  The influenza virus PA endonuclease is an attractive target for the development of novel anti-influenza virus therapeutics, which are urgently needed because of the emergence of drug-resistant viral strains. Reported PA inhibitors are assumed to chelate the divalent metal ion(s) (Mg2+ or Mn2+) in the enzyme's catalytic site, which is located in the N-terminal part of PA (PA-Nter). In the present work, a series of salicylaldehyde thiosemicarbazone derivatives have been synthesized and evaluated for their ability to inhibit the PA-Nter catalytic activity. Compounds 1-6 have been evaluated against influenza virus, both in enzymatic assays with influenza virus PA-Nter and in virus yield assays in MDCK cells. In order to establish a structure-activity relationship, the hydrazone analogue of the most active thiosemicarbazone has also been evaluated. Since chelation may represent a mode of action of such class of molecules, we studied the interaction of two of them, one with and one without biological activity versus the PA enzyme, towards Mg2+, the ion that is probably involved in the endonuclease activity of the heterotrimeric influenza polymerase complex. The crystal structure of the magnesium complex of the o-vanillin thiosemicarbazone ligand 1 is also described. Moreover, docking studies of PA endonuclease with compounds 1 and 2 were performed, to further analyse the possible mechanism of action of this class of inhibitors.

  DOI：

  10.1007/s00775-015-1292-0
• 作为产物：
  描述：

  2,3-二羟基苯甲醛 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (E)-2-(2,3-dihydroxybenzylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  三齿硫半碳环铜配合物的体外和体内抗癌活性：阐明尚未探索的药理学靶标

  摘要：

  某些金属配合物可能具有很好的抗肿瘤活性，因为在过去的五十年中，顺铂在治疗中的应用已得到证明。作为基于内源金属的抗癌化合物的实例，特别是铜络合物引起了广泛的关注。在本文中，我们介绍了具有不同取代的水杨醛硫代半脲配体的一系列铜（II）配合物的合成和活性。在体外在一组细胞系（HCT-15，LoVo和LoVo奥沙利铂耐药结肠癌，A375黑色素瘤，BxPC3和PSN1胰腺腺癌，BCPAP甲状腺癌，2008年卵巢癌，HEK293非转化胚胎癌）中评估了配体和铜配合物的活性肾脏），突出了金属配合物的显着活性，在某些情况下在低纳摩尔范围内。铜（II）配合物1-6还针对结肠（HCT-15）和胰腺（PSN1）癌细胞的3D椭球体进行了筛选，并取得了良好的效果。还报道了有关铜（II）配合物作用机理的详细研究：它们能够有效抑制铜结合蛋白蛋白质二硫键异构酶，蛋白质二硫键异构酶最近已成为癌症治疗的新治疗靶标。在C57BL

  DOI：

  10.1016/j.ejmech.2020.112266

文献信息

• 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。
• Discovery of New Hydrazone-Thiazole Polyphenolic Antioxidants through Computer-Aided Design and In Vitro Experimental Validation
  作者：Gabriel Marc、Anca Stana、Mihaela Tertiş、Cecilia Cristea、Alexandra Ciorîţă、Ștefan-Mihai Drăgan、Vlad-Alexandru Toma、Raluca Borlan、Monica Focșan、Adrian Pîrnău、Laurian Vlase、Smaranda Oniga、Ovidiu Oniga

  DOI：10.3390/ijms241713277

  日期：——

  Oxidative stress is linked to a series of diseases; therefore, the development of efficient antioxidants might be beneficial in preventing or ameliorating these conditions. Based on the structure of a previously reported compound with good antioxidant properties and on computational studies, we designed several catechol derivatives with enhanced antioxidant potential. The compounds were synthesized and physicochemically characterized, and their antioxidant activity was assessed through different antiradical, electron transfer and metal ions chelation assays, their electrochemical behavior and cytotoxicity were studied. The results obtained in the in vitro experiments correlated very well with the in silico studies; all final compounds presented very good antioxidant properties, generally superior to those of the reference compounds used. Similarly, the results obtained from studying the compounds’ electrochemical behavior were in good agreement with the results of the antioxidant activity evaluation assays. Regarding the compounds’ cytotoxicity, compound 7b had a dose-dependent inhibitory effect against all cell lines. In conclusion, through computer-aided design, we developed several catechol thiazolyl-hydrazones with excellent antioxidant properties, of which compound 7b, with two catechol moieties in its structure, exhibited the best antioxidant activity.

  氧化应激与一系列疾病有关；因此，开发高效的抗氧化剂可能有利于预防或改善这些疾病。基于之前报道的一种具有良好抗氧化性的化合物的结构和计算研究，我们设计了几种具有更强抗氧化潜力的儿茶酚衍生物。我们合成了这些化合物并对其进行了物理化学表征，通过不同的抗自由基、电子传递和金属离子螯合实验评估了它们的抗氧化活性，还研究了它们的电化学行为和细胞毒性。体外实验所获得的结果与硅学研究结果有很好的相关性；所有最终化合物都具有很好的抗氧化性，总体上优于所使用的参考化合物。同样，化合物的电化学行为研究结果与抗氧化活性评估实验结果也非常吻合。在化合物的细胞毒性方面，化合物 7b 对所有细胞株都有剂量依赖性抑制作用。总之，通过计算机辅助设计，我们开发出了几种具有优异抗氧化性能的儿茶酚噻唑肼类化合物，其中化合物 7b 的结构中有两个儿茶酚分子，其抗氧化活性最佳。
• Synthesis of a new hydrazone-based schiff base: Spectroscopy, single crystal, DNA binding and theoretical studies
  作者：Khurram Shahzad Munawar、Saqib Ali、Iqra Shafiq、Muhammad Ashfaq、Muhammad Nawaz Tahir、Saadia Haq、Norah Alhokbany、Sarfraz Ahmed

  DOI：10.1016/j.molstruc.2024.137979

  日期：2024.7

  For this, various kinds of investigations such as frontier molecular orbital (FMO), UV–Vis, global reactivity parameters (GRPs), transition density matrix (TDM), density of states (DOS), natural population analysis (NPA), and natural bond orbital analysis (NBO) were executed at M06 functional. A good agreement was examined between XRD and DFT findings of molecular geometric parameters. Notably, in comparison

  以氨基硫脲和2,3-二羟基苯甲醛为原料，合成了一种新型氨基硫脲基希夫碱。所制备的缩氨基硫脲通过元素(CHN)、FT-IR、1H和13C NMR技术进行了表征。此外，利用单晶X射线衍射（SC-XRD）技术探测了分子结构，证实了不对称单元中具有两个独立分子的烯醇互变异构形式。分子单元之间的差异通过分子叠加图确定。通过赫什菲尔德表面分析探索了各种分子间相互作用和固态组装稳定性。进行空隙分析以检查晶体单元的机械稳定性。采用吸收相互作用法，利用缩氨基硫脲与鲑鱼精子DNA（SS-DNA）的结合能力来探讨其生物活性。伴随着生物活性，还通过 DFT 方法在 M06/6–311 G (d,p) 上探索了所得晶体的光电特性，例如非线性光学特性。为此，各种研究，如前沿分子轨道（FMO）、紫外-可见光、全局反应参数（GRP）、跃迁密度矩阵（TDM）、态密度（DOS）、自然总体分析（NPA）和自然键轨道分析（NBO）是在
• 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.
• US9622993B2
  申请人：——

  公开号：US9622993B2

  公开（公告）日：2017-04-18