N-(2,4-dihydroxybenzylidene)thiosemicarbazide | 6292-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(2,4-dihydroxybenzylidene)thiosemicarbazide
• 英文别名: (E)-2-(2,4-dihydroxybenzylidene)thiosemicarbazone；2,4-Dihydroxybenzaldehyde thiosemicarbazone；[(E)-(2,4-dihydroxyphenyl)methylideneamino]thiourea
• CAS: 6292-76-8
• 化学式: C₈H₉N₃O₂S
• 分子量: 211.244
• InChiKey: DZTQPWJXTVXKJK-ONNFQVAWSA-N

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

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  N-(2,4-dihydroxybenzylidene)thiosemicarbazide 、 一氯频呐酮 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  功能化 1,3-噻唑的合成、单晶结构测定、Hirshfeld 表面分析、晶体空隙、相互作用能和密度泛函理论研究

  摘要：

  目前的研究提供功能化 1,3-噻唑(5a-5b)的合成、X 射线结构测定、Hirshfeld 表面分析、相互作用能和密度泛函理论计算。因此，化合物属于具有P 2 1 /c空间群的单斜晶系。分子间相互作用通过 Hirshfeld 表面 (HS) 分析可视化。另一方面，确定空隙，计算相互作用能，并构建能量框架以阐明在晶体稳定化中占主导地位的能量贡献类型（5a和5b）。此外，密度泛函理论、电子和振动计算提供了对合成化合物（5a和5b）氧化还原行为的深入了解。电子能量、前沿分子轨道密度与振动频率和过渡态以及热力学参数相结合，表明这两种化合物（5a和5b）具有亲电特性。然而，预计化合物5a在电荷转移反应中比5b更易还原。

  DOI：

  10.1016/j.molstruc.2023.135108
• 作为产物：
  描述：

  氨基硫脲 、 2,4-二羟基苯甲醛 以 甲醇 为溶剂， 反应 3.0h， 以89%的产率得到N-(2,4-dihydroxybenzylidene)thiosemicarbazide
  参考文献：
  名称：

  苯甲醛和（硫代）半卡巴zone衍生物的酚类曼尼希碱对半胱氨酸蛋白酶falcipain-2和恶性疟原虫的氯喹抗性菌株的合成和生物学评估。

  摘要：

  合成了目标系列的苯甲醛和（硫代）半卡巴zone衍生物的酚类曼尼希碱基，并在体外针对疟疾半胱氨酸蛋白酶falcipain-2和恶性疟原虫的耐氯喹菌株（W2）进行了体外评估。一系列新型的4-氨基喹啉半咔唑酮是falcipain-2的最有效抑制剂（最有效的抑制剂的IC（50）= 0.63microM），而双喹啉半咔a化合物8f是最有效的抗疟疾化合物，IC（50）为0.07针对W2的microM。化合物8f还弱抑制falcipain-2，IC（50）为3.16microM，尽管它的主要抗寄生虫活性似乎不是由于对该酶的抑制。

  DOI：

  10.1016/j.bmc.2006.09.055

文献信息

• Enhancers of Protein Degradation
  申请人：Wanker Erich

  公开号：US20120282629A1

  公开（公告）日：2012-11-08

  The present invention relates to compounds suitable for modulating huntingtin protein processing and useful for treating or preventing huntingtin-related disorders. The invention provides pharmaceutical compositions comprising said compounds and methods of syntheses thereof.

  本发明涉及适用于调节亨廷顿蛋白处理并用于治疗或预防亨廷顿相关疾病的化合物。本发明提供了包含所述化合物的药物组合物以及其合成方法。
• Investigation of the salicylaldehyde thiosemicarbazone scaffold for inhibition of influenza virus PA endonuclease
  作者：Dominga Rogolino、Alessia Bacchi、Laura De Luca、Gabriele Rispoli、Mario Sechi、Annelies Stevaert、Lieve Naesens、Mauro Carcelli

  DOI：10.1007/s00775-015-1292-0

  日期：2015.10

  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.
• Synthesis, spectroscopic studies and crystal structure of (E)-2-(2,4-dihydroxybenzylidene)thiosemicarbazone and (E)-2-[(1H-indol-3-yl)methylene]thiosemicarbazone
  作者：Mustafa Yıldız、Hüseyin Ünver、Diğdem Erdener、Aşkın Kiraz、Nazan Ocak İskeleli

  DOI：10.1016/j.molstruc.2008.09.008

  日期：2009.2

  Thiosemicarbazone Schiff bases (1 and 2) derived from 2,4-dihydroxybenzaldehyde, indoline-3-carbaldehyde and thiosemicarbazone have been synthesized and their structures were elucidated by elemental analysis. FT-IR, H-1 NMR, C-13 NMR and UV-visible spectroscopic techniques. The structures of compounds 1 and 2 have also been examined cyrstallographically. The title compounds 1 and 2 crystallize in the monoclinic space group C-2/c and triclinic space group P (1) over bar, with unit cell parameters: a = 21.421 (1) and 7.233(1), b = 4.131(1) and 11.166(1), c = 24.942(2) and 13.648(1) angstrom, V = 1856.1(2) and 1019.5(1) angstrom(3), D-x = 1.512 and 1.422 g cm(-3) and Z = 8 and 4, respectively. (C) 2008 Elsevier B.V. All rights reserved.
• ANTI-PARASITIC COMPOUNDS AND METHODS OF THEIR USE
  申请人：Chibale Kelly

  公开号：US20070197495A1

  公开（公告）日：2007-08-23

  The present invention provides a novel class of compounds that disrupt the parasitic infectious life cycle and serve as promising agents for anti-parasitic therapy.
• US9512066B2
  申请人：——

  公开号：US9512066B2

  公开（公告）日：2016-12-06